Editing Robert Downey Jr. (section)

==Career==
===1983–1995: Early work and critical acclaim===
[[File:Robert Downey Jr.jpg|thumb|upright|left|Downey at the premiere of ''[[Air America (film)|Air America]]'' in 1990]]

Downey began building upon his theater roles, making his debut on stage in 1983 at the [[Geva Theatre Center]] in ''Alms for the Middle Class'' for a three-week run.<ref>{{Cite web |last=Greenwood |first=Marcia |title=TBT: Robert Downey Jr. makes stage acting debut at Geva |url=https://www.democratandchronicle.com/story/lifestyle/entertainment/2016/02/18/tbt-robert-downey-jr-makes-stage-acting-debut-geva/80556338/ |access-date=March 8, 2024 |website=Democrat and Chronicle |archive-date=March 8, 2024 |archive-url=https://web.archive.org/web/20240308061728/https://www.democratandchronicle.com/story/lifestyle/entertainment/2016/02/18/tbt-robert-downey-jr-makes-stage-acting-debut-geva/80556338/ |url-status=live }}</ref> He also performed in the short-lived [[off-Broadway]] musical ''American Passion'' at the [[Joyce Theater]] in 1983, produced by [[Norman Lear]].<ref>{{Cite web |title=Actor Robert Downey, Jr. in a scene fr. the Off-Broadway musical "American Passion." (New York) |url=https://digitalcollections.nypl.org/items/880898f0-4a42-0131-e947-58d385a7b928 |access-date=March 8, 2024 |website=NYPL Digital Collections |archive-date=March 8, 2024 |archive-url=https://web.archive.org/web/20240308061728/https://digitalcollections.nypl.org/items/880898f0-4a42-0131-e947-58d385a7b928 |url-status=live }}</ref> In 1984, Downey got a part in the film ''[[Firstborn (1984 film)|Firstborn]]'', where he met [[Sarah Jessica Parker]], and the pair started dating.<ref name="instyle.com">{{Cite web |title=Sarah Jessica Parker and Robert Downey Jr. Used to Throw Water Balloons at Their Hollywood Neighbors |url=https://www.instyle.com/news/tbt-sarah-jessica-parker-robert-downey-jr-relationship |access-date=March 8, 2024 |website=InStyle |archive-date=March 8, 2024 |archive-url=https://web.archive.org/web/20240308061728/https://www.instyle.com/news/tbt-sarah-jessica-parker-robert-downey-jr-relationship |url-status=live }}</ref> In 1985, he was part of the new, younger cast hired for ''[[Saturday Night Live]]''. Downey has said that [[Anthony Michael Hall]], whom he had met and become friends with on the set of his ''[[Weird Science (film)|Weird Science]]'', helped him get the audition.<ref>{{Cite web |last=Moor |first=Ashley |date=October 28, 2021 |title=Inside Anthony Michael Hall's Relationship With Robert Downey Jr |url=https://www.thelist.com/645747/inside-anthony-michael-halls-relationship-with-robert-downey-jr/ |access-date=March 8, 2024 |website=The List |archive-date=March 8, 2024 |archive-url=https://web.archive.org/web/20240308061728/https://www.thelist.com/645747/inside-anthony-michael-halls-relationship-with-robert-downey-jr/ |url-status=live }}</ref> However, he and most of the new crew were dropped and replaced following a year of poor ratings and criticism of the new cast's comedic talents.<ref name="CNN profile" /> ''[[Rolling Stone]]'' magazine named Downey the worst ''SNL'' cast member in its entire run, stating that the "Downey Fail sums up everything that makes ''SNL'' great."<ref>{{cite magazine |last=Sheffield |first=Rob |url=https://www.rollingstone.com/tv/lists/saturday-night-live-all-141-cast-members-ranked-20150211/141-robert-downey-jr-20150211 |title=145. Robert Downey Jr. &#124; 'Saturday Night Live': All 145 Cast Members Ranked |magazine=[[Rolling Stone]] |date=February 11, 2015 |access-date=March 3, 2017 |archive-url=https://web.archive.org/web/20170219004334/http://www.rollingstone.com/tv/lists/saturday-night-live-all-141-cast-members-ranked-20150211/141-robert-downey-jr-20150211 |archive-date=February 19, 2017 |url-status=live }}</ref>

That same year, Downey had a dramatic acting breakthrough when he played [[James Spader]]'s [[sidekick]] in ''[[Tuff Turf]]'' and then a bully in [[John Hughes (filmmaker)|John Hughes]]'s ''Weird Science''. [[Molly Ringwald]] wanted him for the role of Duckie in John Hughes's 1986 film ''[[Pretty in Pink]]'', but the part went to [[Jon Cryer]].<ref name="Kirk Honeycutt">{{cite book |author=Kirk Honeycutt |url=https://books.google.com/books?id=7NyrBwAAQBAJ&pg=PA102 |title=John Hughes: A Life in Film The Genius Behind Ferris Bueller, The Breakfast Club, Home Alone, and More |publisher=Race Point Publishing |year=2015 |isbn=978-1-63106-022-9 |pages=102 |access-date=March 2, 2023 |archive-url=https://web.archive.org/web/20230302233127/https://books.google.com/books?id=7NyrBwAAQBAJ&pg=PA102 |archive-date=March 2, 2023 |url-status=live}}</ref><ref>{{Cite web |date=March 3, 2021 |title=Molly Ringwald Revisits The Crazy Fashion (& Sexual Politics) Of 'Pretty In Pink', 35 Years On |url=https://www.vogue.co.uk/arts-and-lifestyle/article/molly-ringwald-interview |access-date=March 8, 2024 |website=British Vogue |archive-date=April 11, 2021 |archive-url=https://web.archive.org/web/20210411054512/https://www.vogue.co.uk/arts-and-lifestyle/article/molly-ringwald-interview |url-status=live }}</ref> He went on to star with Ringwald in his first lead role in ''[[The Pick-up Artist (1987 film)|The Pick-up Artist]]'' (1987). Because of these and other [[Coming-of-age film|coming-of-age]] films Downey did during the 1980s, he is sometimes named as a member of the [[Brat Pack (actors)|Brat Pack]].<ref name="CNN profile" /><ref>{{cite news |url=http://seattletimes.nwsource.com/html/entertainment/2002575504_downey23.html |title=Downey riding high on the comeback trail |work=[[The Seattle Times]] |first=David |last=Germain |access-date=May 2, 2008 |date=October 23, 2005 |archive-url=https://web.archive.org/web/20110629054425/http://seattletimes.nwsource.com/html/entertainment/2002575504_downey23.html |archive-date=June 29, 2011 |url-status=live }}</ref> Downey moved to Hollywood and lived with fellow actors [[Billy Zane]], who later appeared with Downey in ''[[Only You (1994 film)|Only You]]'' (1994); Sarah Jessica Parker; and [[Kiefer Sutherland]], who starred with Downey in ''[[1969 (film)|1969]]'' (1988).<ref>{{Cite web |date=April 29, 2022 |title=Kiefer Sutherland: 'When the FBI comes running through your house, you remember it' |url=https://www.independent.co.uk/arts-entertainment/music/features/kiefer-sutherland-interview-2022-bloor-street-24-b1997413.html |access-date=March 8, 2024 |website=The Independent|archive-date=March 8, 2024 |archive-url=https://web.archive.org/web/20240308061728/https://www.independent.co.uk/arts-entertainment/music/features/kiefer-sutherland-interview-2022-bloor-street-24-b1997413.html |url-status=live }}</ref><ref>{{Cite news |last=Manzoor |first=Sarfraz |date=March 8, 2024 |title=Kiefer Sutherland: 'I have regrets, but I had a great time' |newspaper=[[The Times]] |url=https://www.thetimes.com/culture/tv-radio/article/kiefer-sutherland-i-have-regrets-but-i-had-a-great-time-38gd3t67j |access-date=March 8, 2024 |issn=0140-0460 |archive-date=March 8, 2024 |archive-url=https://web.archive.org/web/20240308070236/https://www.thetimes.co.uk/article/kiefer-sutherland-i-have-regrets-but-i-had-a-great-time-38gd3t67j |url-status=live }}</ref>

In 1987, Downey played Julian Wells, a drug-addicted rich boy whose life rapidly spirals out of his control, in the film version of the [[Bret Easton Ellis]] novel ''[[Less than Zero (novel)|Less than Zero]]''. His performance, described by [[Janet Maslin]] in ''The New York Times'' as "desperately moving,"<ref>{{cite news |url=https://query.nytimes.com/gst/fullpage.html?res=9B0DE4DA1239F935A35752C1A961948260&sec=&spon= |title=Film: 'Less Than Zero', Young Lives |work=[[The New York Times]] |last=Maslin |first=Janet |access-date=May 2, 2008 |date=November 6, 1987 |author-link=Janet Maslin |archive-date=July 29, 2018 |archive-url=https://web.archive.org/web/20180729141559/https://www.nytimes.com/1987/11/06/movies/film-less-than-zero-young-lives.html |url-status=live }}</ref> was widely praised, though Downey has said that for him "the role was like the [[Ghost of Christmas Yet to Come|ghost of Christmas Future]]" since his drug habit resulted in his becoming an "exaggeration of the character" in real life.<ref name="skin deep">{{cite news |url=http://film.guardian.co.uk/interview/interviewpages/0,6737,1080388,00.html |title=More than skin deep |work=The Guardian |location=UK |date=November 8, 2003 |first=Jon |last=Wilde |access-date=May 2, 2008 |archive-url=https://web.archive.org/web/20080828193924/http://film.guardian.co.uk/interview/interviewpages/0,6737,1080388,00.html |archive-date=August 28, 2008 |url-status=live }}</ref> Soon after completing the film, Downey went into rehab for the first time; the episode would be followed by a number of interventions and stints in rehab over the next decade prior to his 1996 arrest.<ref name="telegraph.co.uk">{{Cite web |date=April 26, 2008 |title=Robert Downey Jr: return of the hero |url=https://www.telegraph.co.uk/culture/film/3672926/Robert-Downey-Jr-return-of-the-hero.html |access-date=March 8, 2024 |website=The Telegraph |archive-date=March 8, 2024 |archive-url=https://web.archive.org/web/20240308055522/https://www.telegraph.co.uk/culture/film/3672926/Robert-Downey-Jr-return-of-the-hero.html |url-status=live }}</ref><ref name=":1"/> ''Zero'' drove Downey into films with bigger budgets and names, such as ''[[Chances Are (film)|Chances Are]]'' (1989) with [[Cybill Shepherd]] and [[Ryan O'Neal]], ''[[Air America (film)|Air America]]'' (1990) with [[Mel Gibson]], and ''[[Soapdish]]'' (1991) with [[Sally Field]], [[Kevin Kline]], [[Cathy Moriarty]], and [[Whoopi Goldberg]].<ref>{{cite web|first=Roger|last=Ebert|title=''Chances Are'' Movie Review & Film Summary|url=https://www.rogerebert.com/reviews/chances-are-1989|publisher=Roger Ebert Online|access-date=July 10, 2014|date=March 10, 1989|archive-url=https://web.archive.org/web/20140709042249/http://www.rogerebert.com/reviews/chances-are-1989|archive-date=July 9, 2014|url-status=live}}</ref><ref>{{cite web|first=Ben|last=Child|title=Robert Downey Jr: Hollywood should forgive Mel Gibson|url=https://www.theguardian.com/film/2011/oct/17/robert-downey-jr-mel-gibson|work=[[The Guardian]]|access-date=July 10, 2014|date=October 17, 2011|archive-url=https://web.archive.org/web/20141106021918/http://www.theguardian.com/film/2011/oct/17/robert-downey-jr-mel-gibson|archive-date=November 6, 2014|url-status=live}}</ref><ref>{{cite web|first=Roger|last=Ebert|title=''Soapdish'' Movie Review & Film Summary|url=https://www.rogerebert.com/reviews/soapdish-1991|publisher=Roger Ebert Online|access-date=July 10, 2014|date=May 31, 1991|archive-url=https://web.archive.org/web/20140709004549/http://www.rogerebert.com/reviews/soapdish-1991|archive-date=July 9, 2014|url-status=live}}</ref>

In 1992, he starred as [[Charlie Chaplin]] in ''[[Chaplin (film)|Chaplin]]'', a role for which he prepared extensively, learning how to play the violin as well as tennis left-handed. He had a personal coach in order to help him imitate Chaplin's posture and way of carrying himself.<ref>{{cite news |url=https://query.nytimes.com/gst/fullpage.html?res=9F0CE3D91E3EF932A25757C0A965958260 |title=Film: Once Again The Clowning Gets Physical |work=The New York Times |last=Hornaday |first=Anne |access-date=August 1, 2008 |date=April 11, 1993 |archive-date=July 29, 2018 |archive-url=https://web.archive.org/web/20180729141715/https://www.nytimes.com/1993/04/11/movies/film-once-again-the-clowning-gets-physical.html |url-status=live }}</ref> The role garnered Downey an [[Academy Awards|Academy Award]] nomination for [[Academy Award for Best Actor|Best Actor]] at the [[65th Academy Awards|65th Academy Awards ceremony]], losing to [[Al Pacino]] in ''[[Scent of a Woman (1992 film)|Scent of a Woman]]''.<ref>{{cite magazine |url=https://www.rollingstone.com/blogs/traverstake/2008/03/the-strange-case-of-iron-man-r.php |title=The Strange Case of Iron Man Robert Downey Jr. |magazine=Rolling Stone |last=Travers |first=Peter |access-date=August 1, 2008 |date=March 13, 2008 |archive-url=https://web.archive.org/web/20080619105209/http://www.rollingstone.com/blogs/traverstake/2008/03/the-strange-case-of-iron-man-r.php |archive-date=June 19, 2008 |url-status=live }}</ref> In 1993, he appeared in the films ''[[Heart and Souls]]'' with [[Alfre Woodard]] and [[Kyra Sedgwick]] and ''[[Short Cuts]]'' with [[Matthew Modine]] and [[Julianne Moore]], along with a documentary that he wrote about the 1992 presidential campaigns titled ''[[The Last Party (film)|The Last Party]]'' (1993).<ref>{{cite web|first=Janet|last=Maslin|title=Heart and Souls (1993) Reviews/Film: A Yuppie Haunted (Really) By Other People's Problems|url=https://www.nytimes.com/movie/review?res=9F0CE1DF1F38F930A2575BC0A965958260|work=[[The New York Times]]|access-date=July 10, 2014|date=August 13, 1993|archive-url=https://web.archive.org/web/20140907192823/http://www.nytimes.com/movie/review?res=9F0CE1DF1F38F930A2575BC0A965958260|archive-date=September 7, 2014|url-status=live}}</ref><ref>{{cite magazine|first=Peter|last=Travers|title=Short Cuts {{!}} Movie Review|url=https://www.rollingstone.com/movies/reviews/short-cuts-19931003|magazine=[[Rolling Stone]]|access-date=July 10, 2014|date=October 3, 1993|archive-url=https://web.archive.org/web/20140715085201/http://www.rollingstone.com/movies/reviews/short-cuts-19931003|archive-date=July 15, 2014|url-status=live}}</ref><ref>{{cite web|first=Chris|last=Heath|title=Robert Downey Jr: 21 Years Ago|url=https://www.gq.com/entertainment/movies-and-tv/201305/robert-downey-jr-in-1992|work=[[GQ]]|access-date=July 10, 2014|date=April 2013|archive-url=https://web.archive.org/web/20140714220218/http://www.gq.com/entertainment/movies-and-tv/201305/robert-downey-jr-in-1992|archive-date=July 14, 2014|url-status=live}}</ref> He starred in the 1994 films ''[[Only You (1994 film)|Only You]]'' with [[Marisa Tomei]], and ''[[Natural Born Killers]],'' with [[Woody Harrelson]].<ref>{{cite web|first=Roger|last=Ebert|title=''Only You'' Movie Review & Film Summary|url=https://www.rogerebert.com/reviews/only-you-1994|publisher=Roger Ebert Online|access-date=July 10, 2014|date=October 7, 1994|archive-url=https://web.archive.org/web/20140708231109/http://www.rogerebert.com/reviews/only-you-1994|archive-date=July 8, 2014|url-status=live}}</ref><ref>{{cite web|first=Britt|last=Hayes|title=See the Cast of 'Natural Born Killers' Then and Now|date=January 11, 2014 |url=https://screencrush.com/natural-born-killers-then-and-now/|publisher=Screen Crush|access-date=July 10, 2014|archive-url=https://web.archive.org/web/20140717050018/http://screencrush.com/natural-born-killers-then-and-now/|archive-date=July 17, 2014|url-status=live}}</ref> He then subsequently appeared in ''[[Restoration (1995 film)|Restoration]]'' (1995), ''[[Richard III (1995 film)|Richard III]]'' (1995), ''[[Home for the Holidays (1995 film)|Home for the Holidays]]'' (1995), ''[[Two Girls and a Guy]]'' (1997),<ref>{{cite web|url=https://www.rogerebert.com/reviews/two-girls-and-a-guy-1998|author=Ebert, Roger|title=Two Girls and a Guy|website=RogerEbert.com|publisher=Chicago Sun-Times|date=April 24, 1998|access-date=November 27, 2018|archive-url=https://web.archive.org/web/20191226102959/https://www.rogerebert.com/reviews/two-girls-and-a-guy-1998|archive-date=December 26, 2019|url-status=live}}</ref> as Special Agent John Royce in ''[[U.S. Marshals (film)|U.S. Marshals]]'' (1998), and in ''[[Black and White (1999 drama film)|Black and White]]'' (1999).<ref>{{cite web|first=Janet|last=Maslin|title=Restoration (1994) Film Review: The King's Vet, Beard and Cuckolder|url=https://www.nytimes.com/movie/review?res=9904EEDC1239F93AA15751C1A963958260|work=The New York Times|access-date=July 10, 2014|date=December 29, 1995|archive-url=https://web.archive.org/web/20140716121405/http://www.nytimes.com/movie/review?res=9904EEDC1239F93AA15751C1A963958260|archive-date=July 16, 2014|url-status=live}}</ref><ref>{{cite web|title=Ian McKellen's Richard III {{!}} Notes |url=http://www.mckellen.com/cinema/richard/notes.htm |publisher=McKellen.com |access-date=July 10, 2014 |url-status=dead |archive-url=https://web.archive.org/web/20090430075105/http://www.mckellen.com/cinema/richard/notes.htm |archive-date=April 30, 2009 }}</ref><ref>{{cite web|title=Robert Downey Jr. Turned Down Heather Graham|url=http://www.entertainmentwise.com/news/41729/robert-downey-jr-turned-down-heather-graham|publisher=Entertainment Wise|access-date=July 10, 2014|date=April 15, 2008|archive-url=https://web.archive.org/web/20140714153216/http://www.entertainmentwise.com/news/41729/robert-downey-jr-turned-down-heather-graham|archive-date=July 14, 2014|url-status=live}}</ref><ref>{{cite web|first=Roger|last=Ebert|title=''Black and White'' Movie Review & Film Summary|url=https://www.rogerebert.com/reviews/black-and-white-2000|publisher=Roger Ebert Online|access-date=July 10, 2014|date=April 5, 2000|archive-url=https://web.archive.org/web/20140709003938/http://www.rogerebert.com/reviews/black-and-white-2000|archive-date=July 9, 2014|url-status=live}}</ref>

===1996–2001: Addiction-related setbacks and ''Ally McBeal''===
From 1996 through 2001, Downey was arrested several times on charges related to drugs, including [[cocaine]], [[heroin]], and marijuana.<ref>{{cite magazine |url=http://content.time.com/time/nation/article/0,8599,98373,00.html |title=Will Robert Downey Jr.'s Case Spark a Change in Drug Sentencing? |magazine=Time |last=Reaves |first=Jessica |access-date=May 1, 2008 |date=February 7, 2001 |archive-url=https://web.archive.org/web/20160826172534/http://content.time.com/time/nation/article/0,8599,98373,00.html |archive-date=August 26, 2016 |url-status=live }}</ref> He went through drug treatment programs and spent time in county jail and prison. He explained in 1999 to a judge: "It's like I have a shotgun in my mouth, and I've got my finger on the trigger, and I like the taste of the [[Gunmetal|gun metal]]." He said he had been addicted to drugs since the age of eight due to the fact that his father had been giving them to him.<ref name="bbc jail">{{cite news |url=http://news.bbc.co.uk/2/hi/americas/413283.stm |title=Addicted Downey Jnr jailed |work=BBC News |access-date=May 1, 2008 |date=August 6, 1999 |archive-url=https://web.archive.org/web/20120330114926/http://news.bbc.co.uk/2/hi/americas/413283.stm |archive-date=March 30, 2012 |url-status=live }}</ref>

In early 1996, after becoming increasingly concerned for Downey, [[Sean Penn]] and [[Dennis Quaid]] knocked on his door, took his keys, and took him to a rehab center in [[Tucson, Arizona|Tucson]]; however, Downey escaped and checked himself out a few days later.<ref name="telegraph.co.uk"/> In June 1996, Downey was arrested for possession of heroin, cocaine, [[crack cocaine]], and an unloaded [[.357 Magnum]] handgun while he was speeding down [[Sunset Boulevard]]. A month later, while on parole, he wandered into a neighbor's home through the unlocked front door while under the influence of a controlled substance and fell asleep in one of the beds.<ref name="carrtimes">{{cite news |url=https://www.nytimes.com/2008/04/20/movies/20carr.html?_r=1&ref=movies&pagewanted=all&oref=slogin |title=Been Up, Been Down. Now? Super. |work=The New York Times |last=Carr |first=David |access-date=May 1, 2008 |date=April 20, 2008 |archive-url=https://web.archive.org/web/20130525000357/http://www.nytimes.com/2008/04/20/movies/20carr.html?_r=1&ref=movies&pagewanted=all&oref=slogin |archive-date=May 25, 2013 |url-status=live }}</ref><ref>{{cite magazine |url=http://www.time.com/time/arts/article/0,8599,1731600-2,00.html |title=Robert Downey Jr.: Back from the Brink |magazine=Time |last=Winters Keegan |first=Rebecca |access-date=May 1, 2008 |date=April 16, 2008 |archive-url=https://web.archive.org/web/20120118135333/http://www.time.com/time/arts/article/0,8599,1731600-2,00.html |archive-date=January 18, 2012 |url-status=dead }}</ref> The family refused to press trespassing charges.<ref name=":1">{{Cite magazine |date=August 1, 2000 |title=Robert Downey Jr. Speaks From Prison |url=https://www.vanityfair.com/hollywood/2000/08/robert-downey-jr-prison |access-date=March 8, 2024 |magazine=Vanity Fair |archive-date=March 29, 2023 |archive-url=https://web.archive.org/web/20230329131535/https://www.vanityfair.com/hollywood/2000/08/robert-downey-jr-prison |url-status=live }}</ref> The tape of the neighbor's 911 call was made available online, and it became known as the "Goldilocks incident".<ref>{{Cite web |title=The star who came back from the depths {{!}} Robert Downey Jr {{!}} The Guardian |url=https://www.theguardian.com/film/2008/aug/24/robertdowneyjr.usa |access-date=March 8, 2024 |website=amp.theguardian.com |date=August 23, 2008 |archive-date=March 8, 2024 |archive-url=https://web.archive.org/web/20240308055522/https://amp.theguardian.com/film/2008/aug/24/robertdowneyjr.usa |url-status=live }}</ref> In November 1996, after spending time in court-ordered rehab, he received a further six months of live-in rehab, three years' probation, and was ordered to undergo compulsory drug testing.<ref name=":1" /> In 1997, he missed one of the court-ordered drug tests and had to spend six months in the Los Angeles County jail.<ref>{{cite web|first=Robert W.|last=Welkos|title=Actor Robert Downey Jr. Given 6-Month Jail Term|url=https://www.latimes.com/archives/la-xpm-1997-dec-09-me-62196-story.html|work=[[Los Angeles Times]]|access-date=July 10, 2014|date=December 9, 1997|archive-url=https://web.archive.org/web/20140714224120/http://articles.latimes.com/1997/dec/09/local/me-62196|archive-date=July 14, 2014|url-status=live}}</ref> After being released, he went into a court-ordered 120-day rehab program.<ref name=":1" />

{{multiple image
 | align = right
 | direction = vertical
 | width = 125
 | header = 
 | image1 = Actor Robert Downey Jr. photographed by the California Department of Corrections.jpg
 | alt1 = A mugshot of actor Robert Downey Jr smiling for his headshot in 1999
 | caption1 = Mugshot from his arrest in August 1999
 | image2 = Rdowneymug2.jpg
 | alt2 = A mugshot of actor Robert Downey Jr in 2001
 | caption2 = Mugshot from his arrest in April 2001
}}

In 1999, after being clean during the shooting of ''[[Wonder Boys (film)|Wonder Boys]]'', Downey relapsed. During this time, he was struggling with legal bills and had lost his house in Malibu.<ref name="telegraph.co.uk"/> After Downey missed another required drug test in 1999, he was arrested again. Despite Downey's lawyer, [[Robert Shapiro (lawyer)|Robert Shapiro]], assembling the same team of lawyers that had successfully defended [[O. J. Simpson]] during his [[O. J. Simpson murder case|criminal trial for murder]],<ref name="bbc jail" /> Downey was sentenced to a three-year prison term at the [[California Substance Abuse Treatment Facility and State Prison]] in [[Corcoran, California]].<ref name=":2" /> At the time of the arrest, all of Downey's film projects had wrapped and were close to release. He had been hired to provide the voice of the [[devil]] on the [[NBC]] animated television series ''[[God, the Devil and Bob]]'', but was fired when he failed to attend rehearsals.<ref name=":2">{{cite news |url=https://variety.com/1999/film/news/downey-gets-3-yr-prison-term-for-parole-violations-1117750121/ |title=Downey gets 3-year prison term for parole violations |work=[[Variety (magazine)|Variety]] |last=Ault |first=Susanne |access-date=August 8, 2008 |date=August 6, 1999 |archive-date=September 8, 2013 |archive-url=https://web.archive.org/web/20130908061612/http://variety.com/1999/film/news/downey-gets-3-yr-prison-term-for-parole-violations-1117750121/ |url-status=live }}</ref><ref>{{cite news |url=http://news.bbc.co.uk/1/hi/entertainment/375887.stm |title=Downey Jr back in jail |work=BBC News |access-date=August 8, 2008 |date=July 23, 1999 |archive-url=https://web.archive.org/web/20021108122740/http://news.bbc.co.uk/1/hi/entertainment/375887.stm |archive-date=November 8, 2002 |url-status=live }}</ref>

After spending nearly a year in the [[California Substance Abuse Treatment Facility and State Prison, Corcoran|California Substance Abuse Treatment Facility and State Prison]], Downey, on condition of posting a $5,000 bail, was unexpectedly freed when a judge ruled that his collective time in incarceration facilities (from the initial 1996 arrests) had qualified him for early release.<ref name="toughest"/> A week after his 2000 release, Downey joined the cast of the hit television series ''[[Ally McBeal]]'', playing a new love interest.<ref>{{cite news |url=http://news.bbc.co.uk/2/hi/entertainment/875828.stm |title=Downey Jr lands McBeal role |work=BBC News |access-date=May 1, 2008 |date=August 11, 2000 |archive-url=https://web.archive.org/web/20120330113511/http://news.bbc.co.uk/2/hi/entertainment/875828.stm |archive-date=March 30, 2012 |url-status=live }}</ref> He was nominated for the [[Primetime Emmy Award for Outstanding Supporting Actor in a Comedy Series]] and won the [[Golden Globe Award for Best Supporting Actor – Series, Miniseries or Television Film]].<ref>{{cite news |url=https://www.foxnews.com/story/bada-bing-sopranos-leads-emmy-pack |title=Bada Bing! Sopranos Leads Emmy Pack |work=Fox News Channel |access-date=May 1, 2008 |date=July 12, 2001 |archive-url=https://web.archive.org/web/20100604005442/http://www.foxnews.com/story/0,2933,29375,00.html |archive-date=June 4, 2010 |url-status=live }}</ref><ref>{{cite news |url=http://news.bbc.co.uk/2/hi/entertainment/1091051.stm |title=Downey Jr's Golden acting career |work=BBC News |access-date=May 1, 2008 |date=January 22, 2001 |archive-url=https://web.archive.org/web/20120330113204/http://news.bbc.co.uk/2/hi/entertainment/1091051.stm |archive-date=March 30, 2012 |url-status=live }}</ref> He also appeared as a writer and singer on [[Vonda Shepard]]'s ''Ally McBeal: For Once in My Life'' album and sang with [[Sting (musician)|Sting]] a duet of "[[Every Breath You Take]]" in an episode of the series. Despite the apparent success, Downey claimed that his performance on the series was overrated and said, "It was my lowest point in terms of addictions. At that stage, I didn't give a fuck whether I ever acted again."<ref name="skin deep" /> In January 2001, Downey was scheduled to play the role of [[Prince Hamlet|Hamlet]] in a [[Los Angeles]] stage production directed by [[Mel Gibson]].<ref>{{cite news|url=http://news.bbc.co.uk/1/hi/entertainment/935383.stm|title=Gibson Downey Jr becomes Hamlet|work=BBC News|date=September 21, 2000|access-date=June 1, 2008|archive-url=https://web.archive.org/web/20090115082537/http://news.bbc.co.uk/1/hi/entertainment/935383.stm|archive-date=January 15, 2009|url-status=live}}</ref>

Before the end of his first season on ''Ally McBeal'', Downey was arrested on [[Thanksgiving]] in 2000, when his room at [[Merv Griffin]]'s Hotel and Givenchy Spa in [[Palm Springs, California]], was searched by the police, who were responding to an anonymous 911 call. Downey was under the influence of a controlled substance and in possession of cocaine and [[valium]].<ref>{{cite news |url=https://query.nytimes.com/gst/fullpage.html?res=9E07E0D6113BF934A25754C0A9679C8B63 |title=Boldface Names |last=Baron |first=James |work=The New York Times |access-date=May 1, 2008 |date=July 17, 2001 |archive-date=November 23, 2018 |archive-url=https://web.archive.org/web/20181123202900/https://www.nytimes.com/2001/07/17/nyregion/boldface-names-279722.html |url-status=live }}</ref><ref>{{cite magazine|url=https://ew.com/article/2001/04/24/robert-downey-jr-arrested-la/|title=Robert Downey Jr. arrested in L.A.|last=Angulo|first=Sandra P.|magazine=Entertainment Weekly|access-date=October 2, 2019|date=April 24, 2001|archive-url=https://web.archive.org/web/20181020140606/https://ew.com/article/2001/04/24/robert-downey-jr-arrested-la/|archive-date=October 20, 2018|url-status=live}}</ref> ''Rolling Stone'' later ran a six-page investigation into the weekend's events.<ref name="telegraph.co.uk"/> Despite the fact that, if convicted, he would have faced a prison sentence of up to four years and eight months, he signed on to appear in at least eight more ''Ally McBeal'' episodes.<ref>{{cite news |url=http://news.bbc.co.uk/2/hi/entertainment/1171634.stm |title=Downey Jr signs McBeal deal |work=BBC News |access-date=May 11, 2008 |date=February 15, 2001 |archive-url=https://web.archive.org/web/20120330120605/http://news.bbc.co.uk/2/hi/entertainment/1171634.stm |archive-date=March 30, 2012 |url-status=live }}</ref>

In April 2001, while Downey was on parole, a Los Angeles police officer found him wandering barefoot in [[Culver City]]. He was arrested on suspicion of being under the influence of drugs but was released a few hours later,<ref>{{cite news |url=https://www.foxnews.com/story/robert-downey-jr-fired-from-ally-mcbeal-after-another-arrest |title=Robert Downey Jr. Fired From Ally McBeal After Another Arrest |agency=Associated Press |work=Fox News Channel |access-date=May 11, 2008 |date=April 25, 2001 |archive-url=https://web.archive.org/web/20091003025020/http://www.foxnews.com/story/0,2933,15876,00.html |archive-date=October 3, 2009 |url-status=live }}</ref> even though tests showed he had cocaine in his system.<ref name="wired drug">{{cite news |url=https://www.wired.com/entertainment/hollywood/news/2001/05/44194 |title=Robert Downey Jr.'s Drug 'Deal' |agency=Reuters |work=[[Wired (website)|Wired]] |access-date=May 11, 2008 |date=May 31, 2001 |archive-url=https://web.archive.org/web/20090110195743/http://www.wired.com/entertainment/hollywood/news/2001/05/44194 |archive-date=January 10, 2009 |url-status=live }}</ref> After this last arrest, ''Ally McBeal'' executives ordered last-minute rewrites and reshoots and fired Downey, despite the fact that Downey's character had resuscitated ''Ally McBeal''{{'}}s ratings.<ref>{{cite news |url=https://www.nytimes.com/2002/04/18/business/this-season-to-be-last-for-ally-mcbeal.html?scp=1&sq=%20%22This%20Season%20to%20Be%20Last%20for%20%27Ally%20McBeal&st=cse |title=This Season to Be Last for 'Ally McBeal' |last=Carter |first=Bill |work=The New York Times |access-date=September 9, 2010 |date=April 18, 2002 |archive-url=https://web.archive.org/web/20130525000609/http://www.nytimes.com/2002/04/18/business/this-season-to-be-last-for-ally-mcbeal.html?scp=1&sq=%20%22This%20Season%20to%20Be%20Last%20for%20%27Ally%20McBeal&st=cse |archive-date=May 25, 2013 |url-status=live }}</ref> The Culver City arrest also cost him a role in the high-profile film ''[[America's Sweethearts]]'',<ref name="wired drug" /> and the subsequent incarceration prompted Gibson to cancel his ''Hamlet'' production. In July 2001, Downey pleaded [[Nolo contendere|no contest]] to the Palm Springs charges, avoiding jail time. Instead, he was sent into drug rehabilitation and received three years of probation, benefiting from [[California Proposition 36 (2000)|California Proposition 36]], which had been passed the year before with the aim of helping nonviolent drug offenders overcome their addictions instead of sending them to jail.<ref name="toughest" /><ref>{{cite news |url=https://transcripts.cnn.com/show/se/date/2001-07-16/segment/03 |title=Robert Downey Jr. to Enter Plea Agreement on Drug Charges |work=CNN |access-date=May 11, 2008 |date=July 16, 2001 |archive-url=https://web.archive.org/web/20120110111727/http://edition.cnn.com/TRANSCRIPTS/0107/16/se.03.html |archive-date=January 10, 2012 |url-status=live }}</ref> Downey spent a year at the court-ordered drug-treatment facility. By this time, Downey was homeless, too much of an insurance liability to be employable, and on the verge of bankruptcy.<ref name="telegraph.co.uk"/>

The book ''Conversations with Woody Allen'' reports that director [[Woody Allen]] wanted to cast Downey and [[Winona Ryder]] in his 2003 film ''[[Melinda and Melinda]]'' but was unable to do so because he could not get insurance on them. Allen stated, "We couldn't get bonded. The [[completion guarantee|completion bonding]] companies would not bond the picture unless we could insure them. We were heartbroken because I had worked with Winona before [on ''[[Celebrity (1998 film)|Celebrity]]''] and thought she was perfect for this and wanted to work with her again. And I had always wanted to work with Bob Downey and always thought he was a huge talent."<ref name="Conversations With Woody Allen">{{cite book|last1=Lax|first1=Eric|author-link1=Eric Lax|orig-year=First published 2007|chapter=Chapter 1: The Idea|title=Conversations With Woody Allen: His Films, the Movies, and Moviemaking. Updated and expanded.|type=E-book|edition=1st|location=New York|publisher=[[Alfred A. Knopf]]|year= 2009|isbn=978-1400031498|lccn=2009012210|oclc=232980446|ol=23192563M}}</ref>

In a December 18, 2000, article for ''[[People (magazine)|People]]'' magazine titled "Bad to Worse", Downey's stepmother, Rosemary, told author Alex Tresnlowski that Downey had been diagnosed with [[bipolar disorder]] "a few years ago" and added that this was "the reason he has a hard time staying sober. What hasn't been tried is medication and intensive [[psychotherapy]]."<ref name="BadToWorse">{{cite web|url=https://people.com/archive/cover-story-bad-to-worse-vol-54-no-26/|title=Bad to Worse|last=Tresnlowski|first=Alex|work=People|date=December 18, 2000|access-date=October 2, 2019|archive-url=https://web.archive.org/web/20190808221202/https://people.com/archive/cover-story-bad-to-worse-vol-54-no-26/|archive-date=August 8, 2019|url-status=live}}</ref> In the same article, Dr. Manijeh Nikakhtar, a Los Angeles psychiatrist and co-author of ''Addiction or Self-Medication: The Truth'', claimed she received a letter from Downey in 1999, during his time at Corcoran II, asking for advice on his condition. She discovered that "no one had done a complete [psychiatric] evaluation [on him] ... I asked him flat out if he thought he was bipolar, and he said, 'Oh yeah. There are times I spend a lot of money and I'm hyperactive, and there are other times I'm down.'"<ref name="BadToWorse" />

In an article for the March 2007 issue of ''[[Esquire (magazine)|Esquire]]'', Downey stated that he wanted to address "this whole thing about the bipolar" after receiving a phone call from "the Bipolar Association" asking him about being bipolar. When Downey denied he had ever said he was bipolar, the caller quoted the ''People'' article, to which Downey replied, "'No! ''Dr. Malibusian'' said [I said I was bipolar] ... ', and they go, 'Well, it's been written, so we're going to quote it.'"<ref name="EsquireMarch2007">{{cite web|url=http://www.esquire.com/features/ESQ0307downeyjr|title=May God Bless and Keep Robert Downey Jr.|last=Raab|first=Scott|work=Esquire|date=March 2007|access-date=November 1, 2010|archive-url=https://web.archive.org/web/20140114215426/http://www.esquire.com/features/ESQ0307downeyjr|archive-date=January 14, 2014|url-status=live}}</ref> Downey flatly denied being "[[Major depressive disorder|depressed]] or [[Hypomania|manic]]" and said that previous attempts to diagnose him with any kind of [[Mental disorder|psychiatric]] or [[mood disorder]] have always been skewed because "the guy I was seeing didn't know I was smokin' crack in his bathroom. You can't make a diagnosis until somebody's sober."<ref name="EsquireMarch2007" />

===2001–2008: Recovery and comeback===
After five years of substance abuse, arrests, rehabilitation, and relapse, Downey was ready to work toward a full recovery from drugs and return to his career. In discussing his failed attempts to control his addictive behavior in the past, Downey told [[Oprah Winfrey]] in November 2004 that "when someone says, 'I really wonder if maybe I should go to rehab?' Well, uh, you're a wreck, you just lost your job, and your wife left you. Uh, you might want to give it a shot."<ref name="OprahPartTwo">{{YouTube|0_K_3h1KBS8|''The Oprah Winfrey Show''}}, second segment, November 22, 2004. Retrieved March 16, 2013.</ref> He added that after his last arrest in April 2001, when he knew he would likely be facing another stint in prison or another form of incarceration such as court-ordered rehab, "I said, 'You know what? I don't think I can continue doing this.' And I reached out for help, and I ran with it. You can reach out for help in kind of a half-assed way and you'll get it and you won't take advantage of it. It's not that difficult to overcome these seemingly ghastly problems ... what's hard is to decide to do it."<ref name="OprahPartTwo" />

Downey got his first post-rehabilitation acting job in August 2001, lip-syncing in the video for [[Elton John]]'s single "[[I Want Love]]".<ref>{{cite web |url=http://www.mtv.com/news/articles/1445963/20010803/john_elton.jhtml |title=Elton John Casts Robert Downey Jr. In His New Video |access-date=May 3, 2008 |last=Schumacher-Rasmussen |first=Eric |date=August 3, 2001 |publisher=MTV News |archive-url=https://web.archive.org/web/20100315085700/http://www.mtv.com/news/articles/1445963/20010803/john_elton.jhtml |archive-date=March 15, 2010 |url-status=dead }}</ref> Video director [[Sam Taylor-Wood]] shot 16 takes of the video and used the last one because, according to John, Downey looked completely relaxed and "the way he underplays it is fantastic."<ref>{{cite web|url=http://www.mtv.com/bands/j/john_elton/news_feature_101201/ |title=Elton John: California Love (Interview) |access-date=May 3, 2008 |last=Rankin |first=Rebecca |publisher=MTV News |url-status=dead |archive-url=https://web.archive.org/web/20080726214913/http://www.mtv.com/bands/j/john_elton/news_feature_101201/ |archive-date=July 26, 2008 }}</ref> Downey was able to return to the big screen after [[Mel Gibson]], who had been a close friend to Downey since both had co-starred in ''Air America'', paid Downey's insurance bond for the 2003 film ''[[The Singing Detective (film)|The Singing Detective]]'' (directed by his ''Back to School'' co-star Keith Gordon).<ref name="gibson"/> Gibson's gamble paved the way for Downey's comeback, and Downey returned to mainstream films in the mid-2000s with ''[[Gothika]]'', for which producer [[Joel Silver]] withheld 40% of Downey's salary until after production wrapped as insurance against his addictive behavior. Similar clauses became standard in his contracts throughout the 2000s.<ref name="insurance">{{cite episode |title=Robert Downey Jr. |series=Shootout |series-link=Shootout (TV series) |network=[[AMC (TV network)|AMC]] |airdate=July 14, 2006}}</ref> Silver, who was getting closer to Downey as he dated his assistant Susan Levin (later [[Susan Downey]]), also got the actor the leading role in the [[comedy thriller]] ''[[Kiss Kiss Bang Bang]]'', the directorial debut of screenwriter [[Shane Black]].<ref>{{cite web|url=https://www.hollywoodreporter.com/features/lethal-weapon-wunderkind-party-boy-892186|title='Lethal Weapon' Wunderkind (and Former Party Boy) Shane Black Is Back ... and Still Looking for Action|access-date=May 13, 2016|last=Svetkey|first=Benjamin|work=The Hollywood Reporter|date=May 13, 2016|archive-url=https://web.archive.org/web/20170108152533/http://www.hollywoodreporter.com/features/lethal-weapon-wunderkind-party-boy-892186|archive-date=January 8, 2017|url-status=live}}</ref>

After ''[[Gothika]]'', Downey was cast in a number of leading and supporting roles, including well-received work in a number of semi-independent films: ''[[A Guide to Recognizing Your Saints]]'', ''[[Good Night, and Good Luck]];'' [[Richard Linklater]]'s dystopian, [[Rotoscoping|rotoscoped]] ''[[A Scanner Darkly (film)|A Scanner Darkly]]'' (in which Downey plays the role of a drug addict); and [[Steven Shainberg]]'s fictional biographical film of [[Diane Arbus]], ''[[Fur (film)|Fur]]'', in which Downey's character represented the two biggest influences on Arbus's professional life, [[Lisette Model]] and [[Marvin Israel]].<ref>{{cite news |url=https://www.washingtonpost.com/wp-dyn/content/article/2006/11/10/AR2006111000293_pf.html |title=A 'Fur'-Fetched Portrait of Arbus? Precisely! Says the Filmmaker |newspaper=The Washington Post |last=Frey |first=Jennifer |date=November 12, 2006 |access-date=May 15, 2008 |archive-url=https://web.archive.org/web/20121111131919/http://www.washingtonpost.com/wp-dyn/content/article/2006/11/10/AR2006111000293_pf.html |archive-date=November 11, 2012 |url-status=live }}</ref> Downey also received great notice for his roles in more mainstream fare such as ''Kiss Kiss Bang Bang'' and [[Walt Disney Studios Motion Pictures|Disney's]] poorly received ''[[The Shaggy Dog (2006 film)|The Shaggy Dog]]''.<ref>{{cite web|first=Mike |last=D'Angelo|title=Actors of the Year |page=7|url=http://www.esquire.com/features/the-screen/greatperformances1207-7|work=[[Esquire (magazine)|Esquire]]|access-date=July 10, 2014|date=November 20, 2007|url-status=dead|archive-url=https://web.archive.org/web/20150103121925/http://www.esquire.com/features/the-screen/greatperformances1207-7|archive-date=January 3, 2015}}</ref>

On November 23, 2004, Downey released his debut musical album, ''[[The Futurist (Robert Downey Jr. album)|The Futurist]]'', on [[Sony Classical]], for which he designed the cover art and the track listing label on the CD with his son Indio.<ref name="AlbumCredits">As listed in the credits on the CD version of ''The Futurist''.</ref> The album received mixed reviews,<ref>{{cite news |url=http://media.www.bcheights.com/media/storage/paper144/news/2004/12/09/TheScene/Sound.Byte.Robert.Downey.The.Futurist-825969.shtml |title=Robert Downey Jr. The Futurist |work=[[The Heights (newspaper)|The Heights]] |first=Nicole |last=Pensiero |date=December 9, 2004 |access-date=August 6, 2008 |url-status=dead |archive-url=https://web.archive.org/web/20090108053050/http://media.www.bcheights.com/media/storage/paper144/news/2004/12/09/TheScene/Sound.Byte.Robert.Downey.The.Futurist-825969.shtml |archive-date=January 8, 2009 }}</ref><ref>{{cite news |url=http://music.msn.com/music/album-review/robert-downey-jr/the-futurist/ |title=The Futurist: Critic's Review |publisher=MSN Music |last=Collar |first=Matt |access-date=August 6, 2008 |archive-url=https://web.archive.org/web/20120616071434/http://music.msn.com/music/album-review/robert-downey-jr/the-futurist/ |archive-date=June 16, 2012 |url-status=dead }}</ref> but Downey stated in 2006 that he probably would not do another album, as he felt that the energy he put into doing the album was not compensated.<ref>{{cite news |url=https://www.theguardian.com/theobserver/2006/mar/26/features.magazine37 |title=This Much I Know: Robert Downey Jr |work=The Observer |location=UK |last=Horkins |first=Tony |date=March 26, 2006 |access-date=May 11, 2008 |archive-url=https://web.archive.org/web/20140213142940/http://www.theguardian.com/theobserver/2006/mar/26/features.magazine37 |archive-date=February 13, 2014 |url-status=live }}</ref> In 2006, Downey returned to television when he did [[voice acting]] on ''[[Family Guy]]'' in the episode "[[The Fat Guy Strangler]]". Downey had previously telephoned the show's production staff and asked if he could produce or assist in episode creation, as his son Indio is a fan of the show. The producers of the show accepted the offer and created the character of [[Pewterschmidt family|Patrick Pewterschmidt]], [[Lois Griffin]]'s long-lost, [[Mental disorder|mentally disturbed]] brother, for Downey.<ref name="Sheridan">{{cite AV media |people=Sheridan, Chris|year=2005|title=Family Guy season 4 DVD commentary for the episode 'The Fat Guy Strangler'|medium=DVD|publisher=20th Century Fox}}</ref>

Downey signed on with publisher [[HarperCollins]] to write a memoir, which in 2006 was already being billed as a "candid look at the highs and lows of his life and career." In 2008, however, Downey returned his advance to the publishers and canceled the book without further comment.<ref>{{cite news |url=https://www.nbcnews.com/id/wbna25801610 |title=Robert Downey Jr. postpones memoir |publisher=MSNBC |last=Italie |first=Hillel |date=July 30, 2008 |access-date=January 24, 2008 |archive-url=https://web.archive.org/web/20120926000959/http://today.msnbc.msn.com/id/25801610/ns/today-books/ |archive-date=September 26, 2012 |url-status=live }}</ref> In 2007, Downey appeared in [[David Fincher]]'s mystery thriller ''[[Zodiac (film)|Zodiac]]'', which was based on a true story. He played the role of ''[[San Francisco Chronicle]]'' journalist [[Paul Avery]], who was reporting on the [[Zodiac Killer]] case.<ref>{{cite web|first=Paul|last=Harris|title=So Who Was the Zodiac Killer?|url=https://www.theguardian.com/film/2007/apr/15/usa.world|work=The Guardian|access-date=September 2, 2014|date=April 14, 2007|archive-url=https://web.archive.org/web/20170710095041/https://www.theguardian.com/film/2007/apr/15/usa.world|archive-date=July 10, 2017|url-status=live}}</ref>

===2008–2019: Stardom with Iron Man===
[[File:Robert Downey Jr-2008 cropped.JPG|thumb|upright|left|Downey at an event for ''[[Iron Man (2008 film)|Iron Man]]'' in 2008]]

Despite all of the critical success Downey had experienced throughout his career, he had not appeared in a [[blockbuster (entertainment)|"blockbuster" film]]. That changed in 2008, when Downey starred in two critically and commercially successful films, ''[[Iron Man (2008 film)|Iron Man]]'' and ''[[Tropic Thunder]]''. In the article [[Ben Stiller]] wrote for Downey's entry in the 2008 edition of ''[[Time 100|The Time 100]]'', he offered an observation on Downey's commercially successful summer at the box office:

{{blockquote|Yes, Downey is ''Iron Man'', but he really is Actor Man&nbsp;... In the realm where box office is irrelevant and talent is king, the realm that actually means something, he has always ruled, and finally this summer he gets to have his cake and let us eat him up all the way to the multiplex, where his mastery is in full effect. |Ben Stiller, The 2008 ''Time 100'', entry No. 60, "Robert Downey Jr."<ref name="2008Time100">{{cite magazine|last=Stiller|first=Ben|title=The 2008 Time 100, entry No. 60, 'Robert Downey Jr.'|magazine=Time|date=May 11, 2008|url=http://www.time.com/time/specials/2007/article/0,28804,1733748_1733752_1734629,00.html|access-date=April 17, 2009|author-link=Ben Stiller|archive-url=https://web.archive.org/web/20090414111704/http://www.time.com/time/specials/2007/article/0,28804,1733748_1733752_1734629,00.html|archive-date=April 14, 2009|url-status=dead}}</ref>}}

In 2007, Downey was cast as the [[Tony Stark (Marvel Cinematic Universe)|title character]] in the film ''[[Iron Man (2008 film)|Iron Man]]'',<ref>{{cite news |url=http://www.marvel.com/news/moviestories.666 |title=Robert Downey Jr. is Iron Man |publisher=Marvel News |date=September 29, 2006 |access-date=September 29, 2006 |url-status=dead |archive-url=https://archive.today/20120525093422/http://www.marvel.com/news/moviestories.666 |archive-date=May 25, 2012 }}</ref> with director [[Jon Favreau]] explaining the choice by stating, "Downey wasn't the most obvious choice, but he understood what makes the character tick. He found a lot of his own life experience in 'Tony Stark'."<ref>{{cite web |url=http://www.list.co.uk/article/8139-robert-downey-jrs-heroic-comeback/ |title=Robert Downey Jr.'s heroic comeback |access-date=May 2, 2008 |last=O'Loughlin |first=Lucy |date=May 2, 2008 |work=[[The List (magazine)|The List]] |archive-url=https://web.archive.org/web/20080505064610/http://www.list.co.uk/article/8139-robert-downey-jrs-heroic-comeback/ |archive-date=May 5, 2008 |url-status=live }}</ref> Favreau insisted on having Downey, as he repeatedly claimed that Downey would be to ''Iron Man'' what [[Johnny Depp]] is to the [[Pirates of the Caribbean (film series)|''Pirates of the Caribbean'' series]]: a lead actor who could both elevate the quality of the film and increase the public's interest in it.<ref name="carrtimes" /><ref>{{cite web |url=http://www.kansascity.com/entertainment/movies/story/590521.html |title=Jon Favreau rose from obscurity to direct 'Iron Man' |access-date=May 2, 2008 |last=Anderson |first=John |date=April 16, 2008 |publisher=Kansas City.com|archive-url=https://web.archive.org/web/20080503101342/http://www.kansascity.com/entertainment/movies/story/590521.html |archive-date=May 3, 2008|url-status=dead}}</ref><ref>{{cite news |url=http://www.sfgate.com/cgi-bin/article.cgi?f=/c/a/2008/04/28/DD5C107O20.DTL&type=movie |title=Indie cred gave 'Iron Man' filmmaker his shot |access-date=May 2, 2008 |last=Hartlaub |first=Peter |date=May 5, 2008 |work=San Francisco Chronicle |archive-url=https://web.archive.org/web/20120321083121/http://www.sfgate.com/cgi-bin/article.cgi?f=%2Fc%2Fa%2F2008%2F04%2F28%2FDD5C107O20.DTL&type=movie |archive-date=March 21, 2012 |url-status=live }}</ref><ref>{{cite news |url=https://www.washingtonpost.com/wp-dyn/content/article/2008/04/30/AR2008043003729_pf.html |title=Nerve of Steel |access-date=May 2, 2008 |last=Anderson |first=John |date=May 1, 2008 |newspaper=The Washington Post |archive-url=https://web.archive.org/web/20121111131928/http://www.washingtonpost.com/wp-dyn/content/article/2008/04/30/AR2008043003729_pf.html |archive-date=November 11, 2012 |url-status=live }}</ref> For the role, Downey had to gain more than 20 pounds (9 kilograms) of muscle in five months to look like he "had the power to forge iron."<ref>{{cite news |url=http://www.seattlepi.com/movies/361415_downey02.html |title=Robert Downey Jr. has reforged his career in 'Iron Man' |access-date=May 1, 2008 |last=Masuda |first=Sylvia |date=May 2, 2008 |work=Seattle Post-Intelligencer |archive-date=November 16, 2018 |archive-url=https://web.archive.org/web/20181116091610/https://www.seattlepi.com/ae/movies/article/Robert-Downey-Jr-has-reforged-his-career-in-1272139.php |url-status=live }}</ref>

''Iron Man'' was released worldwide between April 30 and May 3, 2008, grossing over $585&nbsp;million worldwide<ref>{{cite web |url=https://boxofficemojo.com/movies/?id=ironman.htm |title=Iron Man (2008) |access-date=June 3, 2013 |website=[[Box Office Mojo]] |archive-url=https://web.archive.org/web/20130531032559/http://www.boxofficemojo.com/movies/?id=ironman.htm |archive-date=May 31, 2013 |url-status=live }}</ref> and receiving rave reviews that cited Downey's performance as a highlight of the film.<ref>{{cite news |url=https://www.washingtonpost.com/wp-dyn/content/article/2008/05/01/AR2008050103883.html?nav=rss_print/style |title='Iron Man' Shows Strength of Character |newspaper=The Washington Post |access-date=May 2, 2008 |date=May 2, 2008 |first=Ann |last=Hornaday |archive-url=https://web.archive.org/web/20121111131940/http://www.washingtonpost.com/wp-dyn/content/article/2008/05/01/AR2008050103883.html?nav=rss_print%2Fstyle |archive-date=November 11, 2012 |url-status=live }}</ref><ref>{{cite web |url=http://www.newsweek.com/id/135033?from=rss |title=Putting the Irony in 'Iron Man' |work=Newsweek |date=May 1, 2008 |access-date=May 2, 2008 |first=David |last=Ansen |archive-url=https://web.archive.org/web/20080506063134/http://www.newsweek.com/id/135033?from=rss |archive-date=May 6, 2008 |url-status=live }}</ref><ref name=trilogy>{{cite news |author=Quint |title=Quint visits the Iron Man production offices! Art! Favreau speaks about sequels (?!?), casting and more!!! |publisher=[[Ain't It Cool News]] |date=February 9, 2007 |url=https://www.aintitcool.com/node/31525 |access-date=February 10, 2007 |archive-url=https://web.archive.org/web/20070212045133/http://www.aintitcool.com/node/31525 |archive-date=February 12, 2007 |url-status=live }}</ref> By October 2008, Downey had agreed to star in two ''Iron Man'' sequels, as part of the [[Iron Man franchise]], as well as ''[[The Avengers (2012 film)|The Avengers]]'', featuring the superhero team that Stark joins, based on Marvel's comic book series ''[[Avengers (comics)|The Avengers]]''.<ref>{{cite news |first=Marc |last=Graser |title=Downey Jr. extends Marvel deal, Actor to star in 'Avengers,' 'Iron Man 3' |work=Variety |url=https://variety.com/2008/film/markets-festivals/downey-jr-extends-marvel-deal-1117994793/ |access-date=October 28, 2008 |date=October 28, 2008 |archive-url=https://web.archive.org/web/20081101031720/http://www.variety.com/article/VR1117994793.html?categoryid=10&cs=1 |archive-date=November 1, 2008 |url-status=live }}</ref> He first reprised the role in a small appearance as Iron Man's [[alter ego]] Tony Stark in the 2008 film ''[[The Incredible Hulk (film)|The Incredible Hulk]]'', as a part of [[Marvel Studios]]' depicting the same [[Marvel Cinematic Universe|Marvel Universe]] on film by providing continuity among the movies.<ref>{{cite news |first=Larry |last=Carroll |title=William Hurt Says New Hulk Is More Heroic, Reveals Iron Man Crossover Scene |publisher=MTV News |url=http://www.mtv.com/movies/news/articles/1579965/20080115/story.jhtml |access-date=April 22, 2008 |archive-url=https://web.archive.org/web/20080123032855/http://www.mtv.com/movies/news/articles/1579965/20080115/story.jhtml |archive-date=January 23, 2008 |url-status=dead }}</ref>

After ''Iron Man'', Downey appeared alongside Ben Stiller and [[Jack Black]] in the Stiller-directed ''[[Tropic Thunder]]''. The three actors play a Hollywood archetype, with Downey playing self-absorbed multi-Oscar-winning [[Australian nationality law|Australian]] method actor Kirk Lazarus{{snd}}as they star in an extremely expensive [[Vietnam War|Vietnam-era]] film called ''Tropic Thunder''. Lazarus undergoes a "controversial skin pigmentation procedure" in order to take on the role of [[African Americans|African-American]] platoon sergeant Lincoln Osiris, which requires Downey to wear dark makeup and a wig. Both Stiller and Downey feared Downey's portrayal of the character could become controversial:

{{blockquote|Stiller says that he and Downey always stayed focused on the fact that they were skewering insufferable actors, not African Americans. "I was trying to push it as far as you can within reality", Stiller explains. "I had no idea how people would respond to it". Stiller screened a rough cut of the film [in March 2008] and it scored high with African Americans. He was relieved at the reaction. "It seems people really embrace it", he said.<ref name=ew>{{cite magazine |first=Adam B. |last=Vary |title=First Look: Stiller's new movie |magazine=Entertainment Weekly |date=March 5, 2008 |url=https://ew.com/article/2008/03/09/first-look-stillers-new-movie/ |access-date=October 2, 2019 |archive-url=https://web.archive.org/web/20191111015309/https://ew.com/article/2008/03/09/first-look-stillers-new-movie/ |archive-date=November 11, 2019 |url-status=live }}</ref>}}

When asked by Harry Smith on CBS's ''The Early Show'' who his model was for Lazarus, Downey laughed before responding, "Sadly, my sorry-ass self."<ref>{{cite web|url=https://www.youtube.com/watch?v=-EU_vi6QgeY|title=Robert Downey Jr. on 'Thunder'|publisher=CBS|date=August 18, 2008|access-date=August 21, 2008|archive-url=https://web.archive.org/web/20130802065746/http://www.youtube.com/watch?v=-EU_vi6QgeY|archive-date=August 2, 2013|url-status=live}}</ref>

Released in the United States on August 13, 2008, ''Tropic Thunder'' received good reviews, with 83% of reviews positive and an average normalized score of 71, according to the review aggregator websites [[Rotten Tomatoes]] and [[Metacritic]], respectively.<ref>{{cite web|title=Tropic Thunder (2008)|url=https://www.rottentomatoes.com/m/tropic_thunder/|website=Rotten Tomatoes|access-date=July 10, 2014|archive-url=https://web.archive.org/web/20140617105502/http://www.rottentomatoes.com/m/tropic_thunder/|archive-date=June 17, 2014|url-status=live}}</ref><ref>{{cite web|title=Tropic Thunder Reviews|url=https://www.metacritic.com/movie/tropic-thunder|publisher=Meta Critic|access-date=July 10, 2014|archive-url=https://web.archive.org/web/20150117110415/http://www.metacritic.com/movie/tropic-thunder|archive-date=January 17, 2015|url-status=live}}</ref> It earned US$26&nbsp;million in its North American opening weekend and retained the number one position for its first three weekends of release. The film grossed $180&nbsp;million in theaters before its release on home video on November 18, 2008. Downey was nominated for the [[Academy Award for Best Supporting Actor]] for his portrayal of Lazarus.<ref>{{cite web|title=The 81st Academy Awards (2009) Nominees and Winners|url=http://www.oscars.org/awards/academyawards/legacy/ceremony/81st-winners.html|publisher=Academy of Motion Picture Arts and Sciences|access-date=July 10, 2014|archive-url=https://web.archive.org/web/20141006101405/http://www.oscars.org/awards/academyawards/legacy/ceremony/81st-winners.html|archive-date=October 6, 2014|url-status=live}}</ref>

Opening in late April 2009 was a film Downey finished in mid-2008, ''[[The Soloist]]''. The film was delayed from a November 2008 release by [[Paramount Pictures]] due to the studio's tight end-of-year release schedule.<ref name=TheSoloist>{{cite web |url=http://themovingpicture.net/the-soloist-delayed-until-march-2009 |title=The Soloist Delayed Until March 2009 |publisher=The Moving Picture |access-date=March 8, 2010 |archive-url=https://web.archive.org/web/20110724101609/http://themovingpicture.net/the-soloist-delayed-until-march-2009 |archive-date=July 24, 2011 |url-status=dead }}</ref> Critics who had seen the film in 2008 were mentioning it as a possible [[Academy Award]] candidate.<ref>{{cite web|title=2 high-wire performances that pandered to the academy but didn't even get a nomination.|url=http://www.slate.com/articles/arts/the_oscars/2010/03/look_at_me_im_acting_here.html|work=[[Slate (magazine)|Slate]]|access-date=May 12, 2014|first=Eric|last=Hynes|date=March 2010|archive-url=https://web.archive.org/web/20131202221608/http://www.slate.com/articles/arts/the_oscars/2010/03/look_at_me_im_acting_here.html|archive-date=December 2, 2013|url-status=live}}</ref> Downey picked up an Academy Award nomination for the 2008 release year for his role in ''Tropic Thunder''.<ref>{{cite news |first=Todd |last=Leopold |title='Button' hooks 13 Oscar nominations |work=CNN |date=January 22, 2009 |url=http://www.cnn.com/2009/SHOWBIZ/Movies/01/22/oscar.nominations/index.html |access-date=January 22, 2009 |archive-url=https://web.archive.org/web/20090123021901/http://www.cnn.com/2009/SHOWBIZ/Movies/01/22/oscar.nominations/index.html |archive-date=January 23, 2009 |url-status=live }}</ref>
[[File:Robert Downey Jr. - 2019 Disney Legends Awards Ceremony - D23 EXPO 2019 (cropped).jpg|thumb|left|upright|Downey speaking at the 2019 [[Disney Legends|Disney Legends Awards]]]]
The first role Downey accepted after ''Iron Man'' was [[Sherlock Holmes]] in [[Guy Ritchie]]'s adaptation of ''[[Sherlock Holmes (2009 film)|Sherlock Holmes]]''. [[Warner Bros.]] released it on December 25, 2009.<ref>{{cite news |first=Jacques |last=Steinberg |title=Robert Downey Jr. to Play Sherlock Holmes' |work=The New York Times |date=June 11, 2008 |url=https://www.nytimes.com/2008/07/11/arts/11arts-ROBERTDOWNEY_BRF.html?ref=arts |access-date=August 1, 2008 |archive-url=https://web.archive.org/web/20140311022341/http://www.nytimes.com/2008/07/11/arts/11arts-ROBERTDOWNEY_BRF.html?ref=arts |archive-date=March 11, 2014 |url-status=live }}</ref> The film set several box office records in the United States for a Christmas Day release, beating the previous record-holder, 2008's ''[[Marley & Me (film)|Marley & Me]]'', by nearly $10 million, and finished second to ''[[Avatar (2009 film)|Avatar]]'' in a record-setting Christmas weekend box office. ''Sherlock Holmes'' ended up being the [[2009 in film#Highest-grossing films|8th highest-grossing film of 2009]].<ref>{{cite news|first=Grady|last=Smith|date=December 27, 2009|url=http://blog.theboxofficejunkie.com/2009/12/weekend-fix-avatar-and-sherlock-lead.html|title=Avatar, Sherlock Lead The Largest Weekend in Film History! Top 12 Earned $275 Million!|work=The Box Office Junkie|quote=The Top 12 grossed an astonishing $264&nbsp;million over the weekend frame – the largest weekend in film history|access-date=January 31, 2010|url-status=dead|archive-url=https://web.archive.org/web/20091231011638/http://blog.theboxofficejunkie.com/2009/12/weekend-fix-avatar-and-sherlock-lead.html|archive-date=December 31, 2009}}</ref><ref>{{cite web|url=https://boxofficemojo.com/weekend/chart/?yr=2009&wknd=52&p=.htm|title=December 25–27, 2009&nbsp;– Weekend Studio Estimates|work=[[Box Office Mojo]]|access-date=January 31, 2010|archive-url=https://web.archive.org/web/20100203153102/http://boxofficemojo.com/weekend/chart/?yr=2009&wknd=52&p=.htm|archive-date=February 3, 2010|url-status=live}}</ref> When Downey won the Golden Globe for Best Actor in a Motion Picture Musical or Comedy from the Hollywood Foreign Press Association for his role as Sherlock Holmes, he noted in his acceptance speech that he had prepared no remarks because "[[Susan Downey]] told me that [[Matt Damon]] was going to win so don't bother preparing a speech."<ref>{{cite AV media|title=Avengers Star Robert Downey Jr Wins Best Actor Motion Picture Musical or Comedy – Golden Globes 2010|url=https://www.youtube.com/watch?v=f7f1PiHi9Uc|publisher=Dick Clark Productions|quote=First of all, I'd like to thank Susan Downey for telling me that Matt Damon was going to win so don't bother preparing a speech. That was at about 10&nbsp;am.|date=August 19, 2010|access-date=July 10, 2014|archive-url=https://web.archive.org/web/20150524160649/https://www.youtube.com/watch?v=f7f1PiHi9Uc|archive-date=May 24, 2015|url-status=live}}</ref>

Downey returned as Tony Stark in the first of two planned sequels to ''Iron Man'', ''[[Iron Man 2]]'', which was released in May 2010. ''Iron Man 2'' grossed over $623 million worldwide, becoming the [[2010 in film#Highest-grossing films|7th highest-grossing film of 2010]].<ref>{{cite web|url=https://boxofficemojo.com/yearly/chart/?view2=worldwide&yr=2010&p=.htm|title=2010 Worldwide Grosses|work=[[Box Office Mojo]]|access-date=August 28, 2012|archive-url=https://web.archive.org/web/20170222004148/http://boxofficemojo.com/yearly/chart/?view2=worldwide&yr=2010&p=.htm|archive-date=February 22, 2017|url-status=live}}</ref> Downey's other commercial film release of 2010 was the comedy [[road movie|road film]], ''[[Due Date]]''. The movie, co-starring [[Zach Galifianakis]], was released in November 2010<ref>[http://moviesblog.mtv.com/2009/07/27/iron-man-robert-downey-jr-joins-zack-galifianakis-in-the-todd-phillips-comedy-due-date 'Iron Man' Robert Downey Jr. Joins Zack Galifianakis In The Todd Phillips Comedy 'Due Date'] {{Webarchive|url=https://web.archive.org/web/20120409161755/http://moviesblog.mtv.com/2009/07/27/iron-man-robert-downey-jr-joins-zack-galifianakis-in-the-todd-phillips-comedy-due-date |date=April 9, 2012 }}. [[MTV]]. Retrieved December 11, 2010.</ref> and grossed over $211 million worldwide, making it the 36th highest-grossing movie of 2010.<ref>{{cite web|url=https://boxofficemojo.com/yearly/chart/?view2=worldwide&yr=2010&p=.htm|title=2010 Yearly Box Office Results|work=[[Box Office Mojo]]|access-date=December 17, 2011|archive-url=https://web.archive.org/web/20170222004148/http://boxofficemojo.com/yearly/chart/?view2=worldwide&yr=2010&p=.htm|archive-date=February 22, 2017|url-status=live}}</ref> Downey's sole 2011 film credit was ''[[Sherlock Holmes: A Game of Shadows]]'', which opened worldwide on December 16, 2011.<ref>{{cite web|first=Christina|last=Radish|title=Robert Downey Jr. 'Sherlock Holmes: A game of Shadows' Interview|url=https://collider.com/robert-downey-jr-interview-sherlock-holmes-2/|website=Collider|access-date=July 10, 2014|year=2012|archive-url=https://web.archive.org/web/20140714224043/http://collider.com/robert-downey-jr-interview-sherlock-holmes-2/|archive-date=July 14, 2014|url-status=live}}</ref>

In 2012, Downey reprised the role of Tony Stark in ''[[The Avengers (2012 film)|The Avengers]]''. The film received positive reviews<ref>{{cite web |title=Marvel's The Avengers (2012) |url=https://www.rottentomatoes.com/m/marvels_the_avengers/ |website=[[Rotten Tomatoes]] |access-date=August 28, 2012 |archive-url=https://web.archive.org/web/20120826153317/http://www.rottentomatoes.com/m/marvels_the_avengers/ |archive-date=August 26, 2012 |url-status=live }}</ref> and was highly successful at the box office, becoming the third highest-grossing film of all time both in the United States and worldwide.<ref>{{cite news|url=https://www.hollywoodreporter.com/news/box-office-milestone-avengers-number-three-332331|title=Box Office Milestone: 'The Avengers' Becomes No. 3 Pic of All Time With $1.331 Billion|work=[[The Hollywood Reporter]]|first=Pamela|last=McClintock|date=June 2, 2012|access-date=August 28, 2012|archive-url=https://web.archive.org/web/20120815033436/http://www.hollywoodreporter.com/news/box-office-milestone-avengers-number-three-332331|archive-date=August 15, 2012|url-status=live}}</ref> His film, the [[David Dobkin (director)|David Dobkin]]-directed dramedy ''[[The Judge (2014 film)|The Judge]]'',<ref>{{cite web|last=Kit|first=Borys|title='Gossip Girl' Star Leighton Meester Joins Robert Downey Jr. in 'The Judge'|url=https://www.hollywoodreporter.com/news/gossip-girl-star-leighton-meester-432915|work=The Hollywood Reporter|access-date=April 16, 2013|date=April 3, 2013|archive-url=https://web.archive.org/web/20130501231150/http://www.hollywoodreporter.com/news/gossip-girl-star-leighton-meester-432915|archive-date=May 1, 2013|url-status=live}}</ref> a project co-produced by his production company [[Team Downey]], was the opening film at the 2014 [[Toronto International Film Festival]].<ref>{{cite web|title=''#TIFF14 Opens With David Dobkin's The Judge''|url=http://www.tiff.net/whats-on/news-events/tiff14-david-dobkins-the-judge|url-status=dead|archive-url=https://web.archive.org/web/20140911001855/http://www.tiff.net/whats-on/news-events/tiff14-david-dobkins-the-judge|archive-date=September 11, 2014}}</ref> Downey played Tony Stark again in ''[[Iron Man 3]]'' (2013),<ref>{{cite web|url=http://splashpage.mtv.com/2010/10/20/iron-man-3-villains/|title=''Iron Man 3'' Has A Release Date, But What About A Villain?|date=October 20, 2010|access-date=December 24, 2010|archive-url=https://web.archive.org/web/20111105050349/http://splashpage.mtv.com/2010/10/20/iron-man-3-villains/|archive-date=November 5, 2011|url-status=dead}}</ref> ''[[Avengers: Age of Ultron]]'' (2015), ''[[Captain America: Civil War]]'' (2016), ''[[Spider-Man: Homecoming]]'' (2017),<ref name="Downey">{{cite web|url=https://www.hollywoodreporter.com/heat-vision/robert-downey-jr-joins-spider-885829 |title=Robert Downey Jr. Joins 'Spider-Man: Homecoming' |last=Kit |first=Borys |work=[[The Hollywood Reporter]] |date=April 21, 2016 |access-date=April 21, 2016 |archive-url=https://web.archive.org/web/20160421180921/http://www.hollywoodreporter.com/heat-vision/robert-downey-jr-joins-spider-885829 |archive-date=April 21, 2016 |url-status=live }}</ref> ''[[Avengers: Infinity War]]'' (2018), and ''[[Avengers: Endgame]]'' (2019).<ref name="Downey" /> Three of his scenes from ''The Avengers'' and ''Avengers: Endgame'' were used as archive footage in the [[Glorious Purpose (Loki season 1)|first episode]] of the [[Disney+]] series ''[[Loki (TV series)|Loki]]''.<ref>{{Cite web|date=June 9, 2021|title='Loki' Director Kate Herron on Shooting New 'Avengers: Endgame'-Era Footage|url=https://www.hollywoodreporter.com/tv/tv-features/loki-avengers-endgame-marvel-disney-1234965274/|access-date=June 10, 2021|website=The Hollywood Reporter|archive-date=June 9, 2021|archive-url=https://web.archive.org/web/20210609195951/https://www.hollywoodreporter.com/tv/tv-features/loki-avengers-endgame-marvel-disney-1234965274/|url-status=live}}</ref> Downey hosted ''[[The Age of A.I.]]'', a YouTube documentary series released in 2019.<ref>{{Cite web|url=https://deadline.com/2019/12/the-age-of-a-i-robert-downey-jr-hosts-youtube-documentary-series-watch-the-trailer-1202807411/|title='The Age Of A.I.': Robert Downey Jr. Hosts YouTube Documentary Series – Watch The Trailer|last1=Pedersen|first1=Erik|date=December 12, 2019|website=Deadline|access-date=January 18, 2020|archive-url=https://web.archive.org/web/20191231191546/https://deadline.com/2019/12/the-age-of-a-i-robert-downey-jr-hosts-youtube-documentary-series-watch-the-trailer-1202807411/|archive-date=December 31, 2019|url-status=live}}</ref>

=== 2020–present: ''Oppenheimer'' and expansion ===
In 2020, Downey starred in [[Dolittle (film)|''Dolittle'']], playing the [[Doctor Dolittle|titular character]], depicted in the film as a 19th-century Welsh veterinarian who can communicate with animals. This was the second film from Team Downey. It was a [[Box-office bomb|box office disappointment]] and received negative reviews from critics, who called it "too long [and] lifeless."<ref>{{Cite web |last1=D'Alessandro |first1=Anthony |date=January 18, 2020 |title='Bad Boys For Life' So Good With $68M+; 'Dolittle' Still A Dud With $30M+ – Box Office Update |url=https://deadline.com/2020/01/bad-boys-for-life-dolittle-1917-weekend-box-office-1202833726/ |url-status=live |archive-url=https://web.archive.org/web/20200120213703/https://deadline.com/2020/01/bad-boys-for-life-dolittle-1917-weekend-box-office-1202833726/ |archive-date=January 20, 2020 |access-date=January 19, 2020 |website=Deadline}}</ref>

In 2023, Downey portrayed antagonistic bureaucrat [[Lewis Strauss]] in [[Christopher Nolan]]'s ''[[Oppenheimer (film)|Oppenheimer]]''. He took a pay cut to work on the film, earning $4 million in lieu of his usual $10–20 million upfront salary.<ref>{{Cite web |last=Lang |first=Brent |date=July 20, 2022 |title=Inside Movie Stars' Salaries: Joaquin Phoenix Nabs $20M for ''Joker 2,'' Tom Cruise Heads to Over $100M and More |url=https://variety.com/2022/film/features/movie-star-salaries-joaquin-phoenix-joker-2-tom-cruise-1235320046/ |url-status=live |archive-url=https://web.archive.org/web/20220720160107/https://variety.com/2022/film/features/movie-star-salaries-joaquin-phoenix-joker-2-tom-cruise-1235320046/ |archive-date=July 20, 2022 |access-date=July 21, 2022 |website=[[Variety (magazine)|Variety]]}}</ref> Downey would later describe ''Oppenheimer'' as "the best film" in which he has appeared to date.<ref>{{Cite web |date=July 17, 2023 |title=Robert Downey Jr hails Oppenheimer as his "best film" |url=https://www.digitalspy.com/movies/a44569013/robert-downey-jr-oppenheimer-best-film-career/ |url-status=live |archive-url=https://web.archive.org/web/20230720113845/https://www.digitalspy.com/movies/a44569013/robert-downey-jr-oppenheimer-best-film-career/ |archive-date=July 20, 2023 |access-date=July 20, 2023 |website=[[Digital Spy]]}}</ref> The biopic and Downey's performance received critical acclaim.<ref name="Chang">{{cite news |last1=Chang |first1=Justin |title='Oppenheimer' doesn't show us Hiroshima and Nagasaki. That's an act of rigor not erasure. |url=https://www.latimes.com/entertainment-arts/movies/story/2023-08-11/oppenheimer-atomic-bomb-hiroshima-nagasaki-christopher-nolan |access-date=August 23, 2023 |newspaper=Los Angeles Times |date=August 11, 2023 |archive-date=August 23, 2023 |archive-url=https://web.archive.org/web/20230823033158/https://www.latimes.com/entertainment-arts/movies/story/2023-08-11/oppenheimer-atomic-bomb-hiroshima-nagasaki-christopher-nolan |url-status=live }}</ref><ref>{{Cite web |last=Wong |first=Henry |date=July 21, 2023 |title='Oppenheimer' is Robert Downey Jr.'s Best Role in Years |url=https://www.esquire.com/uk/culture/a44586992/oppenheimer-review-robert-downey-jr/ |access-date=July 27, 2023 |website=Esquire |archive-date=July 27, 2023 |archive-url=https://web.archive.org/web/20230727233558/https://www.esquire.com/uk/culture/a44586992/oppenheimer-review-robert-downey-jr/ |url-status=live }}</ref><ref>{{Cite web |last=Moore |first=Sam |date=July 24, 2023 |title=Robert Downey Jr. is at his best in Oppenheimer, which could spark a new chapter for the actor |url=https://www.yahoo.com/entertainment/robert-downey-jr-best-oppenheimer-170854603.html |access-date=July 27, 2023 |website=Yahoo Entertainment |archive-date=July 27, 2023 |archive-url=https://web.archive.org/web/20230727150514/https://www.yahoo.com/entertainment/robert-downey-jr-best-oppenheimer-170854603.html |url-status=live }}</ref> For the role, he won the [[Golden Globe Award for Best Supporting Actor – Motion Picture|Golden Globe Award]], [[BAFTA Award for Best Actor in a Supporting Role|BAFTA Award]], [[Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Supporting Role|Screen Actors Guild Award]], [[Critics' Choice Movie Award for Best Supporting Actor|Critics' Choice Award]], and [[Academy Award for Best Supporting Actor]].<ref name="oppenheimer">{{cite news|url=https://www.washingtonpost.com/national/2024/03/10/supporting-actor-2024-oscars/1b62fa22-df40-11ee-95aa-7384336086f3_story.html|title=Robert Downey Jr. wins his first Oscar for supporting actor role in 'Oppenheimer'|last=Yamat|first=Rio|date=March 10, 2024|newspaper=[[The Washington Post]]|access-date=March 11, 2024}}</ref> Also in 2023, Downey hosted the television series ''Downey's Dream Cars'', where he and his team converted some of Downey's cars from gas to electric.<ref>{{cite magazine|url=https://variety.com/2023/scene/columns/robert-downey-jr-downeys-dream-cars-max-1235647585/|title=Robert Downey Jr.'s 'Dream Cars' Sees 'Iron Man' Star Using Technology to Convert His Cars to Electric — but He's Not Trying to Be Tony Stark|last=Malkin|first=Marc|date=June 22, 2023|magazine=[[Variety (magazine)|Variety]]|access-date=April 26, 2024|archive-date=July 7, 2023|archive-url=https://web.archive.org/web/20230707203538/https://variety.com/2023/scene/columns/robert-downey-jr-downeys-dream-cars-max-1235647585/|url-status=live}}</ref>

Downey next starred in a [[The Sympathizer (miniseries)|2024 television adaptation]] of [[Viet Thanh Nguyen]]'s historical satire novel ''[[The Sympathizer]]'' on [[HBO]], portraying five supporting antagonistic roles representing the American establishment.<ref>{{cite magazine art<!---->icle |last1=Gardner |first1=Chris |title=Park Chan-wook Praises Robert Downey Jr. for Remembering Every Crew Member on 'Sympathizer' Set: "He Gives Them Each a Pat on the Back" |url=https://www.hollywoodreporter.com/movies/movie-news/robert-downey-jr-the-sympathizer-tv-series-park-chan-wook-1235300947/ |magazine=[[The Hollywood Reporter]] |archive-url=https://web.archive.org/web/20230412192321/https://www.hollywoodreporter.com/movies/movie-news/robert-downey-jr-the-sympathizer-tv-series-park-chan-wook-1235300947/ |archive-date=April 12, 2023 |date=January 16, 2023 |url-status=live}}</ref> His multi-role performance earned him an Emmy nomination for [[Primetime Emmy Award for Outstanding Supporting Actor in a Limited or Anthology Series or Movie|Outstanding Supporting Actor in a Limited or Anthology Series or Movie]].<ref>{{cite Magaz<!---->ine |last1=Lewis |first1=Hilary |last2=Nordyke |first2=Kimberly |title=Emmys 2024: List of Nominees |url=https://www.hollywoodreporter.com/tv/tv-news/emmys-nominations-2024-nominees-list-1235950616/ |magazine=[[The Hollywood Reporter]] |publisher=[[Penske Media Corporation]] |archive-url=https://web.archive.org/web/20240717161207/https://www.hollywoodreporter.com/tv/tv-news/emmys-nominations-2024-nominees-list-1235950616/ |archive-date=July 17, 2024 |date=July 17, 2024 |url-status=live}}</ref> Downey Jr. made his [[Broadway (theatre)|Broadway]] debut in ''[[McNeal (play)|McNeal]]'', from playwright [[Ayad Akhtar]], playing Jacob McNeal, a gifted novelist with a difficult family life and a potentially problematic interest in [[artificial intelligence]]. Previews began on September 5, 2024, and opened on September 30 at [[Lincoln Center]]'s [[Vivian Beaumont Theatre]], playing a strictly limited engagement through November 24.<ref>{{cite news|url= https://www.nytimes.com/2024/05/07/theater/robert-downey-jr-ayad-akhtar-broadway.html|title= Robert Downey Jr. to Make Broadway Debut in Ayad Akhtar Play|work= The New York Times|date= May 7, 2024|accessdate= May 7, 2024|last1= Paulson|first1= Michael|archive-date= May 7, 2024|archive-url= https://web.archive.org/web/20240507160511/https://www.nytimes.com/2024/05/07/theater/robert-downey-jr-ayad-akhtar-broadway.html|url-status= live}}</ref>

In July 2024 at [[San Diego Comic-Con]], it was announced that Downey would return to the MCU in a new role as [[Doctor Doom (Marvel Cinematic Universe)|Victor von Doom / Doctor Doom]] in the upcoming films ''[[Avengers: Doomsday]]'' (2026) and ''[[Avengers: Secret Wars]]'' (2027).<ref>{{cite web|url=https://www.hollywoodreporter.com/movies/movie-news/robert-downey-jr-doctor-doom-avengers-1235960026/|title=Robert Downey Jr. Back as Doctor Doom for Two 'Avengers' Movies|date=July 27, 2024|first1=Borys|last1=Kit|first2=Aaron|last2=Couch|first3=Ryan|last3=Gajewski|website=[[The Hollywood Reporter]]|access-date=July 28, 2024|url-status=live|archive-url=https://web.archive.org/web/20240728022926/https://www.hollywoodreporter.com/movies/movie-news/robert-downey-jr-doctor-doom-avengers-1235960026/|archive-date=July 28, 2024}}</ref>