Editing Leonardo DiCaprio (section)

===2002–2009: Work with Martin Scorsese and film production===
{{See also|Martin Scorsese and Leonardo DiCaprio|Appian Way Productions}}

[[File:Leo Scor Diaz(GangsofNY)-.jpg|thumb|DiCaprio attending an event for ''[[Gangs of New York]]'' with [[Martin Scorsese]] and [[Cameron Diaz]] at the [[2002 Cannes Film Festival]]|alt=A photograph Leonardo DiCaprio with Martin Scorsese and Cameron Diaz (from left to right) surrounded by the paparazzi]]

DiCaprio turned down the role of [[Darth Vader|Anakin Skywalker]] in ''[[Star Wars: Episode II – Attack of the Clones]]'' (2002), feeling unprepared to "take that dive" at the time.<ref>{{cite magazine |title=Leonardo DiCaprio: 'I Turned Down the Chance to Play Anakin Skywalker in ''Star Wars''{{'}}|url=https://www.nme.com/news/film/leonardo-dicaprio-i-turned-down-the-chance-to-play-1400784 |magazine=[[NME]] |access-date=November 9, 2019 |date=December 30, 2015 |archive-date=November 8, 2019 |archive-url=https://web.archive.org/web/20191108050254/https://www.nme.com/news/film/leonardo-dicaprio-i-turned-down-the-chance-to-play-1400784 |url-status=live}}</ref> His first film that year was the biopic ''[[Catch Me If You Can]]'', based on the life of [[Frank Abagnale Jr.]], who before his 19th birthday committed [[check fraud]] to make&nbsp;millions in the 1960s.<ref name="cmiyc"/> Directed by [[Steven Spielberg]], the film was shot across 147&nbsp;different locations in 52&nbsp;days, making it "the most adventurous, super-charged movie-making" DiCaprio had experienced yet.<ref>{{cite news |url=http://telepixtvcgi.warnerbros.com/dailynews/extra/12_02/12_12b.html |title=''Catch Me If You Can'' |work=[[Extra (American TV program)|Extra]] |date=December 12, 2002 |access-date=July 3, 2008 |url-status=dead |archive-url=https://web.archive.org/web/20081208031137/http://telepixtvcgi.warnerbros.com/dailynews/extra/12_02/12_12b.html |archive-date=December 8, 2008}}</ref> The film received critical acclaim and grossed $355&nbsp;million against a budget of $52&nbsp;million, becoming his second highest-grossing release after ''Titanic''.<ref>{{cite web |url=https://www.the-numbers.com/movie/Catch-Me-if-You-Can#tab=summary |title=''Catch Me If You Can'' (2002) |publisher=The Numbers |access-date=August 3, 2010 |url-status=live |archive-url=https://web.archive.org/web/20131122201816/http://www.the-numbers.com/movie/Catch-Me-if-You-Can |archive-date=November 22, 2013}}</ref><ref name="mojo"/> [[Roger Ebert]] praised his departure from dark and troubled characters,<ref name="cmiyc">{{cite news |first=Roger |last=Ebert |author-link=Roger Ebert |url=https://www.rogerebert.com/reviews/catch-me-if-you-can-2002 |title=''Catch Me If You Can'' (2002) Review |website=RogerEbert.com |date=September 25, 2002 |access-date=August 3, 2010 |url-status=live |archive-url=https://web.archive.org/web/20140829230500/http://www.rogerebert.com/reviews/catch-me-if-you-can-2002 |archive-date=August 29, 2014}}</ref> and two ''Entertainment Weekly'' critics in 2018 called it DiCaprio's best role, labeling him "delightfully persuasive, deceptive, flirtatious, and sometimes tragic—and we dare you to find a better role, if you can".<ref name="ewbest">{{cite magazine |author=Lawrence, Derek |title=Every Leonardo DiCaprio Film Performance, Ranked |url=https://ew.com/gallery/leonardo-dicaprio-ranking-his-movie-roles/ |access-date=October 26, 2019 |magazine=Entertainment Weekly |date=March 13, 2018|archive-date=November 15, 2019 |archive-url=https://web.archive.org/web/20191115144516/https://ew.com/gallery/leonardo-dicaprio-ranking-his-movie-roles/ |url-status=live}}</ref> DiCaprio received his third Golden Globe nomination for his performance in the film.<ref>{{cite web |title=''Chicago'' Grabs 8 Golden Globe Nominations |url=http://edition.cnn.com/2002/SHOWBIZ/Movies/12/19/golden.globe.nominations/index.html |work=CNN |access-date=July 8, 2015 |date=January 18, 2003 |url-status=live |archive-url=https://web.archive.org/web/20150710164326/http://edition.cnn.com/2002/SHOWBIZ/Movies/12/19/golden.globe.nominations/index.html |archive-date=July 10, 2015}}</ref>

Also in 2002, DiCaprio starred in [[Martin Scorsese]]'s ''[[Gangs of New York]]'', a historical drama set in the mid-19th century in the [[Five Points, Manhattan|Five Points district]] of New York City. Scorsese initially struggled selling his idea of realizing the film until DiCaprio became interested in starring in the film, and thus [[Miramax Films]] got involved with financing the project. Nonetheless, production on the film was plagued by overshooting of budgets and producer-director disagreements, resulting in an eight-month shoot. With a budget of $103&nbsp;million, the film was the most expensive Scorsese had ever made. DiCaprio was drawn to playing Amsterdam Vallon, the young leader of an Irish-American street gang, as it marked a shift from "boyish" roles to a mature leading man.<ref name="tage">{{cite news |date=February 10, 2003 |title=Scorsese's Gang of Acting Heavyweights |work=[[The Age]] |url=https://www.theage.com.au/entertainment/movies/scorseses-gang-of-acting-heavyweights-20030210-gdv7a6.html |url-status=live |access-date=August 3, 2010 |archive-url=https://web.archive.org/web/20100806182045/http://www.theage.com.au/articles/2003/02/09/1044725670402.html |archive-date=August 6, 2010}}</ref> ''Gangs of New York'' earned $193&nbsp;million worldwide and received positive critical response.<ref>{{cite web |url=https://www.the-numbers.com/movie/Gangs-of-New-York |title=''Gangs of New York'' (2002) |publisher=The Numbers |archive-url=https://web.archive.org/web/20131125204908/http://www.the-numbers.com/movie/Gangs-of-New-York |archive-date=November 25, 2013|url-status=live |access-date=August 3, 2010}}</ref><ref>{{cite web |title=''Gangs of New York'' (2002) |date=December 20, 2002 |url=https://www.rottentomatoes.com/m/gangs_of_new_york |publisher=Rotten Tomatoes |access-date=October 8, 2019|archive-url=https://web.archive.org/web/20190517024515/https://www.rottentomatoes.com/m/gangs_of_new_york/ |archive-date=May 17, 2019 |url-status=live}}</ref> Anne Thompson of ''[[The Observer]]'' took note of DiCaprio's "low-key, sturdy performance", but felt that co-star [[Daniel Day-Lewis]] overshadowed him.<ref name="to">{{cite news |url=https://www.theguardian.com/film/2002/dec/22/features.review |title=How Do You Like Your Leonardo DiCaprio? Butch Or Boyish? The Choice Is Yours |last=Thompson |first=Anne |date=December 22, 2002 |work=The Guardian |access-date=August 3, 2010 |archive-url=https://web.archive.org/web/20131104210656/http://www.theguardian.com/film/2002/dec/22/features.review |archive-date=November 4, 2013|url-status=live|url-access=registration}}</ref>

In 2004, DiCaprio founded the production company [[Appian Way Productions]], a namesake of [[Appian Way|the Italian road]].{{sfn|Wight|2012|p=142}} He was interested in finding unique source material and preserving its essence during development, citing previous experiences where the involvement of too many people influenced the final product in a negative way.<ref name="deadline">{{cite news |last1=Fleming |first1=Mike Jr. |title=''Wolf of Wall Street''{{'s}} Leonardo DiCaprio on Creating Fact-Based Black Comedy Without Glorifying Crooks |url=https://deadline.com/2013/12/wolf-of-wall-street-leonardo-dicaprio-657511/ |access-date=October 6, 2019 |work=[[Deadline Hollywood]] |date=December 30, 2013 |archive-url=https://web.archive.org/web/20190811100153/https://deadline.com/2013/12/wolf-of-wall-street-leonardo-dicaprio-657511/ |archive-date=August 11, 2019 |url-status=live}}</ref> DiCaprio first executive-produced ''[[The Assassination of Richard Nixon]]'', which starred [[Sean Penn]] as [[Samuel Byck]],{{sfn|Wight|2012|p=255}} and was screened at the [[2004 Cannes Film Festival]].<ref>{{cite web |url=http://www.festival-cannes.com/en/archives/ficheFilm/id/4200653/year/2004.html |title=''The Assassination of Richard Nixon'' |publisher=[[Cannes Film Festival]] |access-date=December 20, 2015 |url-status=dead |archive-url=https://web.archive.org/web/20131110210248/http://www.festival-cannes.com/en/archives/ficheFilm/id/4200653/year/2004.html |archive-date=November 10, 2013}}</ref> DiCaprio and Scorsese reunited for a biopic of [[Howard Hughes]], an American film director and aviation pioneer suffering from [[obsessive–compulsive disorder]], in ''[[The Aviator (2004 film)|The Aviator]]'' (2004), which DiCaprio also co-produced under Appian Way. He initially developed the project with [[Michael Mann (director)|Michael Mann]] who was eventually replaced by Scorsese.<ref>{{cite news |last1=Fleming |first1=Michael |title=New Line Spruced up |url=https://variety.com/2000/film/news/new-line-spruced-up-1117778736/ |access-date=March 6, 2023 |work=Variety |date=February 25, 2000 |archive-date=March 6, 2023 |archive-url=https://web.archive.org/web/20230306220352/https://variety.com/2000/film/news/new-line-spruced-up-1117778736/ |url-status=live}}</ref><ref>{{cite news |author=Saney, Daniel |title=Scorsese Overspends on ''The Aviator'' |url=https://www.digitalspy.com/movies/a17493/scorsese-overspends-on-the-aviator/ |access-date=March 6, 2023 |work=Digital Spy |date=December 8, 2004 |archive-date=February 10, 2023 |archive-url=https://web.archive.org/web/20230210000518/https://www.digitalspy.com/movies/a17493/scorsese-overspends-on-the-aviator/ |url-status=live}}</ref> ''The Aviator'' became a critical and financial success, grossing $213{{nbsp}}million against its budget of $110{{nbsp}}million.<ref>{{cite web |title=''The Aviator'' (2004) |date=December 25, 2004 |url=https://www.rottentomatoes.com/m/aviator/ |publisher=Rotten Tomatoes |access-date=November 17, 2009 |url-status=live |archive-url=https://web.archive.org/web/20090928003516/http://www.rottentomatoes.com/m/aviator/ |archive-date=September 28, 2009}}</ref><ref>{{cite web |title=''The Aviator'' (2004) |url=https://www.boxofficemojo.com/release/rl742753793/ |publisher=Box Office Mojo |access-date=April 11, 2022 |archive-date=December 21, 2015 |archive-url=https://web.archive.org/web/20151221112126/http://www.boxofficemojo.com/movies/?id=aviator.htm |url-status=live}}</ref> Simond Braund of ''[[Empire (magazine)|Empire]]'' thought DiCaprio convincingly played a complex role and highlighted the scenes depicting Hughes's paranoia and obsession.<ref>{{cite magazine |last1=Braund |first1=Simond |title=''The Aviator'' |url=https://www.empireonline.com/movies/reviews/aviator-review/ |access-date=October 8, 2019 |magazine=[[Empire (magazine)|Empire]] |archive-url=https://web.archive.org/web/20191008160317/https://www.empireonline.com/movies/reviews/aviator-review/ |archive-date=October 8, 2019 |url-status=live}}</ref> He received his first Golden Globe Award for Best Actor — Motion Picture Drama and nominations for an [[Academy Award for Best Actor|Academy Award]], a [[BAFTA Award for Best Actor in a Leading Role|BAFTA Award]] and a [[Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role|Screen Actors Guild Award]].<ref>{{cite news |title=2004 Golden Globe Awards Nominees|url=http://usatoday30.usatoday.com/life/movies/movieawards/goldenglobes/2004-12-13-nominee-list_x.htm |access-date=July 8, 2015 |work=[[USA Today]] |date=December 13, 2004 |url-status=live |archive-url=https://web.archive.org/web/20160304041617/http://usatoday30.usatoday.com/life/movies/movieawards/goldenglobes/2004-12-13-nominee-list_x.htm |archive-date=March 4, 2016}}<br />{{cite web |url=http://www.oscars.org/oscars/ceremonies/2005 |title=Nominees & Winners for the 77th Academy Awards |date=October 5, 2014 |publisher=Academy of Motion Picture Arts and Sciences |access-date=July 12, 2015 |url-status=live |archive-url=https://web.archive.org/web/20160101230853/http://oscars.org/oscars/ceremonies/2005 |archive-date=January 1, 2016}}<br>{{cite news |title=''The Aviator'' Set to Shine at BAFTAs|url=https://www.theguardian.com/film/2005/jan/17/awardsandprizes.baftas2005 |access-date=March 6, 2023 |work=The Guardian |date=January 17, 2005 |archive-date=March 6, 2023 |archive-url=https://web.archive.org/web/20230306220349/https://www.theguardian.com/film/2005/jan/17/awardsandprizes.baftas2005 |url-status=live}}<br>{{cite web |title=The 11th Annual Screen Actors Guild Awards |url=https://www.sagawards.org/awards/nominees-and-recipients/11th-annual-screen-actors-guild-awards |publisher=Screen Actors Guild Awards |access-date=March 6, 2023 |archive-date=January 22, 2021 |archive-url=https://web.archive.org/web/20210122041750/http://www.sagawards.org/awards/nominees-and-recipients/11th-annual-screen-actors-guild-awards |url-status=live}}</ref>

In 2006, DiCaprio starred in the crime film ''[[The Departed]]'' and the political war thriller ''[[Blood Diamond (film)|Blood Diamond]]''. In Scorsese's ''The Departed'', DiCaprio played the role of Billy Costigan, a state trooper working undercover in the [[Irish Mob]] in Boston, someone he characterizes as being in a "constant 24-hour panic attack". DiCaprio especially liked the experience of working with co-star [[Jack Nicholson]], describing a scene with him as "one of the most memorable moments" of his life as an actor.{{sfn|Neibaur|2016|p=159}} In preparation, he visited Boston to interact with people associated with the Irish Mob and gained {{convert|15|lb|kg}} of muscle.<ref>{{cite web |last1=Bell |first1=David |title=Ranking the Craziest Things Actors Have Done for Famous Roles |url=https://collider.com/galleries/craziest-method-acting-for-famous-roles/ |publisher=[[Collider (website)|Collider]] |access-date=December 11, 2019 |date=August 6, 2019 |archive-date=December 11, 2019 |archive-url=https://web.archive.org/web/20191211194215/https://collider.com/galleries/craziest-method-acting-for-famous-roles/ |url-status=live}}</ref> Critically acclaimed,<ref>{{cite web |url=https://www.rottentomatoes.com/m/departed/ |title=''The Departed'' (2006) |date=October 6, 2006 |publisher=Rotten Tomatoes |access-date=October 17, 2009 |url-status=live |archive-url=https://web.archive.org/web/20091118005417/http://www.rottentomatoes.com/m/departed/ |archive-date=November 18, 2009}}</ref> the film grossed $291&nbsp;million against a budget of $90&nbsp;million, becoming DiCaprio and Scorsese's highest-grossing collaboration to that point.<ref>{{cite web |title=''The Departed'' |url=https://www.boxofficemojo.com/title/tt0407887/?ref_=bo_se_r_1 |publisher=Box Office Mojo |access-date=April 10, 2022 |archive-date=April 10, 2022 |archive-url=https://web.archive.org/web/20220410090940/https://www.boxofficemojo.com/title/tt0407887/?ref_=bo_se_r_1 |url-status=live}}</ref><ref name="mojo"/> [[Peter Travers]] of ''Rolling Stone'' praised DiCaprio's and co-star [[Matt Damon]]'s performances as "explosive, emotionally complex", but felt that Nicholson overshadowed the two.<ref>{{cite news |last1=Travers |first1=Peter |title=''The Departed'' |url=https://www.rollingstone.com/movies/movie-reviews/the-departed-250575/ |access-date=October 8, 2019 |magazine=Rolling Stone |date=September 28, 2006 |archive-url=https://web.archive.org/web/20190624045407/https://www.rollingstone.com/movies/movie-reviews/the-departed-250575/ |archive-date=June 24, 2019 |url-status=live}}</ref> Despite DiCaprio's leading role in ''The Departed'', the film's distributor [[Warner Bros. Pictures]] submitted his performance for a Best Supporting Actor nomination at the AMPAS to avoid internal conflict with his part in ''Blood Diamond''.<ref>{{cite news |last1=Tapley |first1=Kristopher |title=10 Years Later: ''The Departed'', the Oscars, and the Non-Campaign Campaign |url=https://variety.com/2016/film/awards/the-departed-oscars-non-campaign-campaign-1201875685/ |access-date=January 8, 2022 |work=Variety |date=October 4, 2016 |archive-url=https://web.archive.org/web/20211227175221/https://variety.com/2016/film/awards/the-departed-oscars-non-campaign-campaign-1201875685/|url-status=live |archive-date=December 27, 2021}}</ref> Instead, his co-star [[Mark Wahlberg]] was nominated, though DiCaprio earned other accolades for ''The Departed'', including a [[Satellite Award for Best Supporting Actor&nbsp;– Motion Picture|Satellite Award for Best Supporting Actor]] and Best Actor nominations at the Golden Globes and BAFTA Awards.<ref name="2006awards"/>

[[File:Leonardo DiCaprio by David Shankbone.jpg|thumb|upright|DiCaprio at the 2007 [[Tribeca Film Festival]]|alt=A picture of Leonardo DiCaprio in a dark suit]]

In ''Blood Diamond'', DiCaprio starred as a diamond smuggler from [[Rhodesia]] who is involved in the [[Sierra Leone Civil War]]. While filming, he worked with 24&nbsp;orphaned children from the [[SOS Children's Village]] in [[Maputo]], [[Mozambique]], and said he was touched by his interactions with them.<ref>{{cite web |url=http://www.sos-usa.org/About-SOS/what-is-sos/sos-supporters/Leonardo-DiCaprio-Works-with-Orphans/Pages/default.aspx |title=Leonardo DiCaprio |archive-url=https://web.archive.org/web/20090106020800/http://www.sos-usa.org/About-SOS/what-is-sos/sos-supporters/Leonardo-DiCaprio-Works-with-Orphans/Pages/default.aspx |archive-date=January 6, 2009 |publisher=[[SOS Children's Villages – USA]] |access-date=January 13, 2009}}</ref> To prepare, he spent six months in Africa, learned about camouflage from people in South African military and interviewed and recorded people in the country to improve his accent.<ref>{{cite magazine |last1=Ressner |first1=Jeffrey |title=Q&A with Leonardo DiCaprio |url=http://content.time.com/time/arts/article/0,8599,1562640-1,00.html |access-date=October 8, 2019 |magazine=Time |date=November 22, 2006 |archive-url=https://web.archive.org/web/20191008100302/http://content.time.com/time/arts/article/0,8599,1562640-1,00.html |archive-date=October 8, 2019 |url-status=live}}</ref> The film received generally favorable reviews,<ref>{{cite web |title=''Blood Diamond'' |publisher=[[Metacritic]] |access-date=June 29, 2010 |url=https://www.metacritic.com/movie/blood-diamond |url-status=live |archive-url=https://web.archive.org/web/20100819043720/http://www.metacritic.com/movie/blood-diamond |archive-date=August 19, 2010}}</ref> and DiCaprio was noted for his South African accent, which is generally known as difficult to imitate.<ref>{{cite news |last1=Sancton |first1=Julian |title=Matt Damon vs. Leonardo DiCaprio: Whose South African (and Southie) Accent is Better? |url=https://www.vanityfair.com/hollywood/2009/12/matt-damon-vs-leonardo-dicaprio-whose-south-african-and-southie-accent-is-better |access-date=August 11, 2015 |magazine=Vanity Fair |date=December 16, 2009 |url-status=live |archive-url=https://web.archive.org/web/20150713160027/http://www.vanityfair.com/hollywood/2009/12/matt-damon-vs-leonardo-dicaprio-whose-south-african-and-southie-accent-is-better |archive-date=July 13, 2015}}</ref> Claudia Puig of the ''[[USA Today]]'' approvingly highlighted DiCaprio's transition from a boy to a man on screen,<ref>{{cite web|last=Puig|first=Claudia|date=December 7, 2006|title=''Blood Diamond'' Shines Forth|url=https://www.usatoday.com/life/movies/reviews/2006-12-07-review-blood-diamond_x.htm|archive-url=https://web.archive.org/web/20090715170610/http://www.usatoday.com/life/movies/reviews/2006-12-07-review-blood-diamond_x.htm|archive-date=July 15, 2009|access-date=October 8, 2019|newspaper=USA Today}}</ref> and [[Ann Hornaday]] of ''[[The Washington Post]]'' similarly noted his growth as an actor since ''The Departed''.<ref>{{cite news |url=https://www.washingtonpost.com/archive/lifestyle/2006/12/08/the-many-facets-of-diamond-span-classbankheadgripping-thriller-packs-a-wallop-amid-a-landscape-of-chaos-and-civil-warspan/4307ce70-a1fd-4e40-b717-66a3cdcd40fd/ |last=Hornaday |first=Ann |title=The Many Facets of 'Diamond' Gripping Thriller Packs a Wallop Amid a Landscape of Chaos and Civil War |newspaper=[[The Washington Post]] |date=December 8, 2006 |access-date=October 8, 2019 |archive-date=March 5, 2022 |archive-url=https://web.archive.org/web/20220305110716/https://www.washingtonpost.com/archive/lifestyle/2006/12/08/the-many-facets-of-diamond-span-classbankheadgripping-thriller-packs-a-wallop-amid-a-landscape-of-chaos-and-civil-warspan/4307ce70-a1fd-4e40-b717-66a3cdcd40fd/ |url-status=live}}</ref> DiCaprio received nominations for an Academy Award and a Golden Globe for ''Blood Diamond''.<ref name="2006awards">{{cite web |title=The 13th Annual Screen Actors Guild Awards |url=http://www.sagawards.org/awards/nominees-and-recipients/13th-annual-screen-actors-guild-awards |publisher=[[Screen Actors Guild Awards]] |access-date=July 8, 2015 |url-status=live |archive-url=https://archive.today/20121204191422/http://www.sagawards.org/awards/nominees-and-recipients/13th-annual-screen-actors-guild-awards |archive-date=December 4, 2012}}<br />{{cite web |title=64th Golden Globe Awards Facts and Figures |url=http://www.hfpa.org/2006/12/64th-golden-globe-awards-facts-and-figures/ |archive-url=https://web.archive.org/web/20150709083640/http://www.hfpa.org/2006/12/64th-golden-globe-awards-facts-and-figures/ |archive-date=July 9, 2015 |publisher=Hollywood Foreign Press Association |access-date=July 8, 2015 |date=December 14, 2006}}<br />{{cite news |last1=Cashin |first1=Rory |title=Opinion: Why Has Leonardo DiCaprio Never Won an Oscar? |url=http://entertainment.ie/cinema/news/Opinion-Why-has-Leonardo-DiCaprio-never-won-an-Oscar/193825.htm |access-date=July 8, 2015 |work=[[Entertainment.ie]] |date=June 18, 2013 |url-status=live |archive-url=https://web.archive.org/web/20150707085703/http://entertainment.ie/cinema/news/Opinion-Why-has-Leonardo-DiCaprio-never-won-an-Oscar/193825.htm |archive-date=July 7, 2015}}<br>{{cite web |url=http://www.pressacademy.com/award_cat/2006/ |title=2006 Winners |publisher=[[International Press Academy]] |access-date=August 3, 2015 |url-status=live |archive-url=https://web.archive.org/web/20150628235847/http://www.pressacademy.com/award_cat/2006/ |archive-date=June 28, 2015}}</ref>

In 2007, DiCaprio produced the comedy drama ''[[Gardener of Eden]]'', which according to ''[[The Hollywood Reporter]]''{{'}}s Frank Scheck "lack[ed] the necessary dramatic urgency or black humor to connect with audiences".<ref>{{cite news |last1=Scheck |first1=Frank |title=''The Gardener of Eden'' |url=https://www.hollywoodreporter.com/review/gardener-eden-159414 |agency=[[Associated Press]]|access-date=December 20, 2015 |work=[[The Hollywood Reporter]] |date=April 26, 2007 |url-status=live |archive-url=https://web.archive.org/web/20151222112758/http://www.hollywoodreporter.com/review/gardener-eden-159414 |archive-date=December 22, 2015}}</ref> Later that year, he produced, co-wrote and narrated ''[[The 11th Hour (2007 film)|The 11th Hour]]'', a documentary on the state of the [[natural environment]] that won the [[Earthwatch Institute|Earthwatch Environmental]] Film Award in 2008.<ref>{{cite web |title=Earthwatch Film Awards |url=https://earthwatch.org/news-media/film-awards |publisher=[[Earthwatch Institute]] |access-date=October 13, 2019 |archive-url=https://web.archive.org/web/20190128135425/https://earthwatch.org/News-Media/Film-Awards |archive-date=January 28, 2019 |url-status=dead}}</ref> DiCaprio's Appian Way produced [[Planet Green]]'s ''[[Greensburg (TV series)|Greensburg]]'' (2008–2010), which ran for three seasons. Set in [[Greensburg, Kansas]], it is about rebuilding the town in a [[Sustainability|sustainable]] way after being hit by the [[2007 Greensburg tornado]].<ref>{{cite web |title=''Greensburg'' Season 3 to Air on Planet Green |url=http://www.greensburgks.org/government/news/greensburg-season-3-to-air-on-planet-green |url-status=dead |archive-url=https://web.archive.org/web/20151222141150/http://www.greensburgks.org/government/news/greensburg-season-3-to-air-on-planet-green |archive-date=December 22, 2015 |access-date=October 7, 2019 |publisher=[[Greensburg, Kansas|Greensburgks.org]]}}</ref> Also in 2008, DiCaprio starred in ''[[Body of Lies (film)|Body of Lies]]'', a spy film based on the [[Body of Lies (novel)|novel of the same name]]. He played one of three agents battling a terrorist organization in the Middle East.<ref name="mtv-bol">{{cite news|last=Carroll|first=Larry|date=August 15, 2007|title=Leonardo DiCaprio and Russell Crowe Will Be a Good 'Fit' in CIA Flick, Ridley Scott Hopes|work=MTV News|url=http://www.mtv.com/movies/news/articles/1567106/story.jhtml|access-date=November 30, 2007|archive-url=https://web.archive.org/web/20090312072055/http://www.mtv.com/movies/news/articles/1567106/story.jhtml|archive-date=March 12, 2009}}</ref> Considering the film to be a throwback to political features of the 1970s like ''[[The Parallax View]]'' (1974) and ''[[Three Days of the Condor]]'' (1975), DiCaprio dyed his hair brown and wore brown contacts for the role.<ref name="mtv-bol" /> The film received mixed reviews from critics,<ref>{{cite web|title=''Body of Lies'' (2008)|url=https://www.rottentomatoes.com/m/10009225-body_of_lies|url-status=live|archive-url=https://web.archive.org/web/20080215011326/http://www.rottentomatoes.com/m/10009225-body_of_lies/|archive-date=February 15, 2008|access-date=February 20, 2008|publisher=Rotten Tomatoes}}</ref> and grossed $118&nbsp;million against a budget of $67.5&nbsp;million.<ref>{{cite web|title=''Body of Lies'' (2008)|url=https://www.the-numbers.com/movie/Body-of-Lies|url-status=live|archive-url=https://web.archive.org/web/20131208124703/http://www.the-numbers.com/movie/Body-of-Lies|archive-date=December 8, 2013|access-date=July 20, 2010|publisher=The Numbers}}</ref>

Later in 2008, DiCaprio collaborated with Kate Winslet for the drama ''[[Revolutionary Road (film)|Revolutionary Road]]'', directed by her then-husband [[Sam Mendes]]. As both actors had been reluctant to make romantic films similar to ''Titanic'', it was Winslet who suggested that they both work with her on a film adaptation of the [[Revolutionary Road|1961 eponymous novel]] by [[Richard Yates (novelist)|Richard Yates]]. She found that the script, by [[Justin Haythe]], had little in common with the 1997 blockbuster.<ref name="cnn">{{cite news |last=Wong |first=Grace |title=DiCaprio Reveals Joys of Fighting With Winslet |url=http://www.cnn.com/2009/SHOWBIZ/Movies/01/23/kate.leo/index.html |work=CNN |date=January 23, 2009 |access-date=January 23, 2009 |url-status=live |archive-url=https://web.archive.org/web/20121105112404/http://www.cnn.com/2009/SHOWBIZ/Movies/01/23/kate.leo/index.html |archive-date=November 5, 2012}}</ref> Playing a couple in a failing marriage in the 1950s, DiCaprio and Winslet spent some time together in preparation, and DiCaprio felt claustrophobic on the small set they used.<ref name="deneuvely"/><ref name="gq">{{cite magazine |last1=Sella |first1=Marshall |title=Leading Man: Leonardo DiCaprio |url=https://www.gq.com/story/leonardo-dicaprio-revolutionary-road-kate-winslet |access-date=October 15, 2019 |magazine=[[GQ (magazine)|GQ]]|date=October 31, 2008 |archive-url=https://web.archive.org/web/20180320060459/https://www.gq.com/story/leonardo-dicaprio-revolutionary-road-kate-winslet |archive-date=March 20, 2018 |url-status=live}}</ref> He saw his character as "unheroic", "slightly cowardly" and someone "willing to be just a product of his environment".<ref>{{cite news |last1=Guzmán |first1=Rafer |title=Leonardo DiCaprio, Kate Winslet in ''Revolutionary Road'' |url=http://www.newsday.com/entertainment/2.828/leonardo-dicaprio-kate-winslet-in-revolutionary-road-1.175825 |access-date=August 11, 2015 |newspaper=[[Newsday]] |date=December 18, 2008 |archive-url=https://web.archive.org/web/20160306101350/http://www.newsday.com/entertainment/2.828/leonardo-dicaprio-kate-winslet-in-revolutionary-road-1.175825 |archive-date=March 6, 2016}}</ref> Peter Travers liked DiCaprio's pairing with Winslet and his multi-layered portrayal of an overwhelmed character,<ref>{{cite magazine |last1=Travers |first1=Peter |title=''Revolutionary Road'' |url=https://www.rollingstone.com/movies/movie-reviews/revolutionary-road-116403/ |access-date=February 3, 2022 |magazine=Rolling Stone |date=December 25, 2008 |archive-date=February 3, 2022 |archive-url=https://web.archive.org/web/20220203202252/https://www.rollingstone.com/movies/movie-reviews/revolutionary-road-116403/ |url-status=live}}</ref> and Marshall Sella of ''[[GQ (magazine)|GQ]]'' called it the "most mature and memorable performance of his lifetime".<ref name="gq" /> DiCaprio earned his seventh Golden Globes nomination for the film.<ref>{{cite web |title=Complete List of Nominations for 2009 Golden Globes |url=http://www.eonline.com/news/72803/complete-list-of-nominations-for-2009-golden-globes |publisher=E! |access-date=July 8, 2015 |date=December 11, 2008 |url-status=live |archive-url=https://web.archive.org/web/20150725234459/http://www.eonline.com/news/72803/complete-list-of-nominations-for-2009-golden-globes |archive-date=July 25, 2015}}</ref> ''Revolutionary Road'' grossed $75.9{{nbsp}}million against its budget of $35{{nbsp}}million.<ref>{{cite web |title=''Revolutionary Road'' |url=https://www.boxofficemojo.com/title/tt0959337/?ref_=bo_se_r_1 |publisher=Box Office Mojo |access-date=April 4, 2022 |archive-date=September 19, 2020 |archive-url=https://web.archive.org/web/20200919172032/https://www.boxofficemojo.com/title/tt0959337/?ref_=bo_se_r_1 |url-status=live}}</ref> He ended the 2000s by producing director [[Jaume Collet-Serra]]'s psychological horror thriller film ''[[Orphan (2009 film)|Orphan]]'' (2009), starring [[Vera Farmiga]], [[Peter Sarsgaard]] and [[Isabelle Fuhrman]]. Although the film received mixed reviews, it was a commercial success.{{sfn|Ochoa|2011|p=75}}