Editing Sean Penn (section)

==Career==
{{expand section|date=July 2023}}

===1974–1989: Early work and breakthrough===
[[File:Sean Penn Cannes.jpg|thumb|left|170px|Penn at the [[1997 Cannes Film Festival]]]]
Penn appeared in a 1974 episode of the ''[[Little House on the Prairie (TV series)|Little House on the Prairie]]'' television series as an extra when his father, Leo, directed some of the episodes.<ref>{{cite web |last=Reier |first=Evan |date=February 20, 2021 |title='Little House on the Prairie': The Uncredited Role Sean Penn Played in the Series |url=https://outsider.com/news/entertainment/little-house-on-the-prairie-uncredited-role-sean-penn-played-series/ |access-date=March 7, 2022 |website=Outsider}}</ref> Penn launched his film career with the action-drama ''[[Taps (film)|Taps]]'' (1981), where he played a military high school cadet.<ref name=tca/> That same year he made his [[Broadway (theatre)|Broadway]] debut in the Kevin Heelan play ''Heartland'' at the [[Century Theatre (Central Park West)|Century Theatre]].<ref>{{cite web|url= https://playbill.com/production/heartland-century-theatre-vault-0000013395|title= Heartland (Broadway, 1981)|website= Playbill|access-date= June 12, 2024}}</ref> A year later, he appeared in the hit comedy ''[[Fast Times at Ridgemont High]]'' (1982), in the role of surfer-stoner Jeff Spicoli; his character helped popularize the word "dude" in popular culture.<ref name=tca/> Next, Penn appeared as Mick O'Brien, a troubled youth, in the drama ''[[Bad Boys (1983 film)|Bad Boys]]'' (1983).<ref name=tca/> The role earned Penn favorable reviews and jump-started his career as a serious actor. He returned to Broadway that same year acting in the [[John Byrne (playwright)|John Byrne]] play ''[[Slab Boys]]'' acting alongside [[Kevin Bacon]], [[Val Kilmer]], [[Jackie Earl Haley]], and [[Madeleine Potter]] at the [[Playhouse Theatre (New York City)|Playhouse Theatre]].<ref>{{cite web|url= https://playbill.com/production/slab-boys-playhouse-theatre-vault-0000013344|title= Slab Boys (Broadway, 1983)|website= Playbill|access-date= June 12, 2024}}</ref>

Penn played [[Andrew Daulton Lee]] in the film ''[[The Falcon and the Snowman]]'' (1985), which closely followed an actual criminal case.<ref name=tca/> Lee was a former drug dealer, convicted of espionage for the [[Soviet Union]] and originally sentenced to life in prison, but was paroled in 1998. Penn later hired Lee as his personal assistant, partly because he wanted to reward Lee for allowing him to play Lee in the film; Penn was also a firm believer in rehabilitation and thought Lee should be successfully reintegrated into society, since he was a free man again.<ref>{{cite web|url=https://www.theguardian.com/film/2005/apr/08/seanpenn|title='When Sean's having fun, it's hard to imagine having more fun'|work=[[The Guardian]]|first=Richard T.|last=Kelly|date=April 8, 2005|access-date=March 3, 2021}}</ref> Penn starred in the drama ''[[At Close Range]]'' (1986) which received critical acclaim.<ref name=tca/> He stopped acting for a few years in the early 1990s, having been dissatisfied with the industry, and focused on making his directing debut.<ref name=tca/>

===1990–1999: Leading man roles and stardom===
In 1990, Penn portrayed Detective Terry Noonan in the [[neo-noir]] ''[[State of Grace (1990 film)|State of Grace]]'' opposite [[Ed Harris]] and [[Gary Oldman]].<ref>{{cite web|url= https://www.rottentomatoes.com/m/state_of_grace|title= State of Grace|website= [[Rotten Tomatoes]]|access-date= June 12, 2024}}</ref> The following year, Penn made his directorial debut with ''[[The Indian Runner]]'' (1991), a crime drama film based on [[Bruce Springsteen]]'s song "[[Highway Patrolman]]", from the 1982 album ''[[Nebraska (album)|Nebraska]]''.<ref name=tca/> [[Janet Maslin]] of ''[[The New York Times]]'' wrote, "Flirting constantly with the dangers of pure self-indulgence, Mr. Penn still manages to keep the improvisatory quality of this painful family drama from becoming overwhelming. For all its hazy excesses, the film seldom loses sight of its story's raw essence."<ref>{{cite news|url= https://www.nytimes.com/1991/09/20/movies/review-film-resolving-the-painful-love-between-2-brothers.html|title= Review/Film; Resolving the Painful Love Between 2 Brothers|work= The New York Times|date= September 20, 1991|access-date= June 11, 2024|last1= Maslin|first1= Janet}}</ref> He also directed music videos, such as [[Shania Twain]]'s "[[Dance with the One That Brought You]]" (1993), [[Lyle Lovett]]'s "North Dakota" (1993). After a brief hiatus from acting, he returned to star in the [[Brian De Palma]] crime drama ''[[Carlito's Way]]'' (1993) acting opposite [[Al Pacino]].<ref>{{cite web|url= https://time.com/collection/100-best-movies/6296072/carlitos-way-1993/|title= Carlito's Way (1993)|website= Time Magazine|date= July 26, 2023|access-date= June 11, 2024}}</ref> Film critic Leonard Klady of ''[[Variety (magazine)|Variety]]'' wrote of his performance, "Penn reminds viewers of what they’ve been missing in his performance as Carlito’s ambitious, amoral lawyer. Without stooping to caricature, he effortlessly captures what is most heinous in the profession."<ref>{{cite web|url= https://variety.com/1993/film/reviews/carlito-s-way-1200434456/|title= Carlito's Way|website= Variety|date= November 8, 1993|access-date= June 12, 2024}}</ref> Penn was he was nominated for the [[Golden Globe Award for Best Supporting Actor – Motion Picture]].<ref>{{cite web|url= https://goldenglobes.com/person/sean-penn/|title= Sean Penn – Golden Globes|website= [[Golden Globe Awards]]|access-date= June 12, 2024}}</ref>

He also directed the indie thriller ''[[The Crossing Guard]]'' (1995) starring [[Jack Nicholson]].<ref>{{cite web|url= https://www.rottentomatoes.com/m/crossing_guard|title= The Crossing Guard|website= [[Rotten Tomatoes]]|access-date= June 12, 2024}}</ref> [[Janet Maslin]] of ''[[The New York Times]]'' wrote, "Penn is a slugger of a film maker, whether pummeling his audience with the obvious or hammering home the heartfelt and true. His second feature...has the same brute force that made his ''[[The Indian Runner|Indian Runner]]'' such a gripping oddity, bearing the distinctive stamp of Mr. Penn's raw, searching style".<ref>{{cite news|url= https://www.nytimes.com/1995/11/15/movies/film-review-from-sean-penn-a-raw-style-and-a-vision.html|title= FILM REVIEW;From Sean Penn, a Raw Style and a Vision|work= The New York Times|date= November 15, 1995|access-date= June 12, 2024|last1= Maslin|first1= Janet}}</ref> That same year he acting alongside [[Susan Sarandon]] starring in the [[Tim Robbins]] directed crime drama playing a racist murderer on [[death row]] in ''[[Dead Man Walking (film)|Dead Man Walking]]'' (1995).<ref>{{cite web |date=February 26, 2022 |title=From 'Dead Man Walking' to 'Milk': 9 Essential Sean Penn Performances |url=https://collider.com/best-sean-penn-performances/ |access-date=March 7, 2022 |website=Collider}}</ref> Critic [[Roger Ebert]] wrote "Penn proves again that he is the most powerful actor of his generation".<ref>{{cite web|url= https://www.rogerebert.com/reviews/dead-man-walking-1996|title= Dead Man Walking|website= [[Roger Ebert|Rogerebert.com]]|access-date= June 11, 2024}}</ref> For his performance he received a nomination for the [[Academy Award for Best Actor]].<ref>{{cite web|url= https://www.oscars.org/oscars/ceremonies/1996|title= The 68th Academy Awards|website= Oscars.org|date= October 5, 2014|access-date= June 11, 2024}}</ref> The following year he acted in [[Nick Cassavetes]] directed romantic drama ''[[She's So Lovely]]'' (1997) opposite his then-wife [[Robin Wright Penn]]. Lisa Schwarzbaum of ''[[Entertainment Weekly]]'' compared the film to the works of [[John Cassavetes]] and wrote that Penn's performance "is so full of heart and talent".<ref>{{cite magazine|url= https://ew.com/article/1997/09/05/shes-so-lovely/|title= She's So Lovely|magazine= [[Entertainment Weekly]]|access-date= June 12, 2024}}</ref> Penn won the [[Cannes Film Festival Award for Best Actor]].<ref>{{cite web|url= https://www.festival-cannes.com/en/p/sean-penn/|title= Sean Penn|website= [[Festival de Cannes]]|access-date= June 11, 2024}}</ref> That same year he acted in the [[Oliver Stone]] directed [[neo-noir]] crime drama ''[[U Turn (1997 film)|U Turn]]'', and [[David Fincher]]'s mystery thriller ''[[The Game (1997 film)|The Game]]''.<ref>{{cite web|url= https://www.rottentomatoes.com/m/u_turn_1997|title= U-Turn (1997)|website= [[Rotten Tomatoes]]|access-date= June 11, 2024}}</ref><ref>{{cite web|url= https://www.rottentomatoes.com/m/the_game|title= The Game (1997)|website= [[Rotten Tomatoes]]|access-date= June 11, 2024}}</ref>

In 1997, he starred in the independent drama ''[[Hurlyburly (film)|Hurlyburly]]'' based on the [[Hurlyburly|1984 play of the same name]] by [[David Rabe]]. [[Peter Bradshaw]] of ''[[The Guardian]]'' wrote, "Sean Penn ends up dominating the film, sweating anxiety and rage from every pore. His charisma and screen presence are undeniable".<ref>{{cite news|url= https://www.theguardian.com/film/2000/apr/07/culture.reviews|title= Hurlyburly|website= The Guardian|date= April 7, 2000|access-date= June 11, 2024|last1= Bradshaw|first1= Peter}}</ref> For his performance he won the [[Volpi Cup for Best Actor]] at the [[Venice International Film Festival]].<ref>{{cite web|url= https://www.indiewire.com/features/general/the-play-is-not-the-thing-anthony-drazan-directs-hurlyburly-82427/|title= The Play Is Not the Thing: Anthony Drazan directs "Hurlyburly"|website= [[IndieWire]]|date= January 4, 1999|access-date= June 11, 2024}}</ref> That same year he had a leading role in the [[Terrence Malick]] epic about the [[World War II]] battle for [[Guadalcanal]] in ''[[The Thin Red Line (1998 film)|The Thin Red Line]]'' (1998) based on the [[The Thin Red Line (novel)|1962 novel of the same name]] by [[James Jones (author)|James Jones]].<ref>{{cite web|url= https://www.criterion.com/films/27513-the-thin-red-line|title= The Thin Red Line|website= [[The Criterion Collection]]|access-date= June 11, 2024}}</ref> The following year he portrayed an egotisitcal jazz guitarist in the [[Woody Allen]] film ''[[Sweet and Lowdown]]'' (1999).<ref>{{cite magazine |last=Wolk |first=Josh Wolk |date=February 17, 2000 |title=Sean Penn discusses Woody Allen's Oscar-worthy directing style |url=https://ew.com/article/2000/02/17/sean-penn-discusses-woody-allens-oscar-worthy-directing-style/ |access-date=March 7, 2022 |magazine=Entertainment Weekly}}</ref> [[Roger Ebert]] described Penn's performances as "master classes in the art of character development".<ref>{{cite web|url= https://www.rogerebert.com/reviews/sweet-and-lowdown-1999|title= Sweet and Lowdown movie review and summary|website= Rogerebert.com|access-date= June 12, 2024}}</ref> For his performance he was nominated for his second [[Academy Award for Best Actor]].<ref>{{cite web|url= https://www.oscars.org/oscars/ceremonies/2000|title= The 72nd Academy Awards|website= Oscars.org|date= April 22, 2015|access-date= June 12, 2024}}</ref>

===2000–2011: Established actor and acclaim===
[[File:Seanpenn1.jpg|thumb|170px|left|Penn in 2008]]
In 2000, Penn acted in [[Julian Schnabel]]'s drama ''[[Before Night Falls (film)|Before Night Falls]]'' opposite [[Javier Bardem]] and [[Kathryn Bigelow]]'s thriller ''[[The Weight of Water (film)|The Weight of Water]]'' with [[Elizabeth Hurley]].<ref>{{cite web|url= https://www.rottentomatoes.com/m/before_night_falls|title= Before Night Falls|website= [[Rotten Tomatoes]]|access-date= June 12, 2024}}</ref><ref>{{cite web|url= https://www.rottentomatoes.com/m/the_weight_of_water|title= The Weight of Water|website= [[Rotten Tomatoes]]|access-date= June 12, 2024}}</ref>
The following year he guest starred on the [[NBC]] sitcom ''[[Friends]]'' portraying Eric, a man who was engaged to [[Phoebe Buffay]]'s sister Ursula, both of whom are played by [[Lisa Kudrow]]. He appeared in two episodes in the [[Friends season 8|eighth season]].<ref>{{cite magazine|url= https://ew.com/gallery/friends-guest-stars/|title= 33 stars you forgot were on Friends|magazine= [[Entertainment Weekly]]|access-date= June 12, 2024}}</ref> That same year he portrayed a mentally handicapped father in the family drama ''[[I am Sam]]'' (2001). His performance led him to his third nomination for the [[Academy Award for Best Actor]].<ref>{{cite web |last1=Peikert |first1=Mark |date=December 31, 2021 |title='I Am Sam' Director Jessie Nelson Wouldn't Make Her Movie the Same Way Now |url=https://www.indiewire.com/2021/12/i-am-sam-director-jessie-nelson-wouldnt-cast-sean-penn-now-1234688266/ |access-date=March 7, 2022 |website=IndieWire}}</ref>

In 2003, he starred in the [[Clint Eastwood]] directed [[Boston]] crime drama ''[[Mystic River (film)|Mystic River]]'' portraying a grieving father looking for his daughter.<ref>{{cite magazine |last=EW Staff |date=March 1, 2004 |title=Sean Penn had a memorable 2004 Oscars moment |url=https://ew.com/article/2004/03/01/sean-penn-had-memorable-2004-oscars-moment/ |access-date=March 7, 2022 |magazine=Entertainment Weekly}}</ref> Penn acted alongside [[Tim Robbins]], [[Laura Linney]], [[Marcia Gay Harden]], and [[Kevin Bacon]]. Film critic Todd McCarthy of ''[[Variety (magazine)|Variety]]'' wrote, "[The] Casting is immaculate. Penn is in top form as the reformed hood whose basic instincts overtake him."<ref>{{cite web|url= https://variety.com/2003/film/awards/mystic-river-3-1200541432/|title= Mystic River|website= Variety|date= May 23, 2003|access-date= June 12, 2024}}</ref> Penn received widespread acclaim for his performance earning [[Mystic River (film)#Accolades|numerous accolades]] including the [[Academy Award for Best Actor|Academy Award]], [[Critics' Choice Movie Award for Best Actor|Critics' Choice Movie Award]], and [[Golden Globe Award for Best Actor in a Motion Picture – Drama|Golden Globe Award]] for Best Actor as well as nominations for the [[BAFTA Award for Best Actor in a Leading Role|BAFTA Award]] and [[Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role|Screen Actors Guild Award]].<ref>{{cite web|url= https://www.imdb.com/title/tt0327056/awards/|title= Mystic River (2003) – Awards|website= [[IMDb]]|access-date= June 12, 2024}}</ref><ref>{{cite web|url= https://www.latimes.com/entertainment-arts/awards/story/2024-02-07/sean-penn-wins-lead-actor-for-mystic-river-in-2004|title= Oscars rewind — 2004: Sean Penn steps up for his work with Clint Eastwood|website= [[Los Angeles Times]]|date= February 7, 2024|access-date= June 12, 2024}}</ref> That same year he acted in [[Alejandro González Iñárritu]]'s [[psychological thriller]] ''[[21 Grams]]'' opposite [[Naomi Watts]] and [[Benicio del Toro]]. For his performance he was nominated for the [[BAFTA Award for Best Actor]] at the [[57th British Academy Film Awards]].<ref>{{cite news|url= http://news.bbc.co.uk/2/hi/entertainment/3490323.stm|title= Bafta awards 2004: The winners|website= [[BBC News]]|date= February 15, 2004|access-date= June 12, 2024}}</ref>

In 2004, Penn played Samuel Bicke, a character based on [[Samuel Byck]], who in 1974 attempted and failed to assassinate President [[Richard Nixon]], in ''[[The Assassination of Richard Nixon]]'' (2004). The same year, he was invited to join the [[Academy of Motion Picture Arts and Sciences]].<ref>{{cite press release |url=http://www.oscars.org/press/pressreleases/2004/04.06.28.html |archive-url=https://web.archive.org/web/20040630082206/http://www.oscars.org/press/pressreleases/2004/04.06.28.html |archive-date=June 30, 2004 |title=Academy Invites 127 to Membership |publisher=Academy of Motion Picture Arts and Sciences |date=June 28, 2004}}</ref> Next, Penn portrayed governor Willie Stark (based on [[Huey Long]]) in an adaptation of [[Robert Penn Warren]]'s classic 1946 American novel ''[[All the King's Men]]'' (2006). The film was a critical and commercial failure, named by a 2010 ''[[Forbes]]'' article as the biggest flop in the last five years.<ref name="Forbes01222010">Pomerantz, Dorothy. [https://www.forbes.com/2010/01/22/sean-penn-eddie-murphy-business-entertainment-star-flops.html Hollywood's Biggest Flops: Big-name stars weren't enough to save these box-office bombs], ''[[Forbes]]'', January 22, 2010.</ref> During this time he directed the mystery film ''[[The Pledge (film)|The Pledge]]'' (2001) and [[Peter Gabriel]]'s "The Barry Williams Show" (2002). Penn gained acclaim for directing the biographical drama survival film ''[[Into the Wild (film)|Into the Wild]]'' (2007). Owen Gleiberman of ''[[Entertainment Weekly]]'' praised wrote, "Penn has written and directed with magnificent precision and imaginative grace".<ref>{{cite magazine|url= https://ew.com/article/2007/09/19/wild-8/|title= Into the Wild|magazine= [[Entertainment Weekly]]|access-date= June 12, 2024}}</ref> For his direction he was nominated for the [[Directors Guild of America Award for Outstanding Directing – Feature Film]].<ref>{{Cite web|url= https://variety.com/2008/film/awards/dga-award-nominees-1117979481/|title= DGA Award Nominees|website= Variety|date= January 23, 2008|access-date= June 12, 2024}}</ref>

[[File:Sean Penn Filming Milk in 2008.jpg|thumb|170px|Penn portraying [[Harvey Milk]] during filming of ''[[Milk (2008 American film)|Milk]]'' in March 2008]]
In November 2008, Penn earned positive reviews for his portrayal of real-life politician and [[gay rights]] activist and icon [[Harvey Milk]] in the [[Gus Van Sant]] directed biographical drama film ''[[Milk (2008 American film)|Milk]]'' (2008). Kirk Honeycutt for ''[[The Hollywood Reporter]]'' wrote, "Penn is one of those actors in complete control of his entire instrument. He uses voice, body movements, line readings and something indefinable within his own psyche to transmigrate into another person’s body and mind".<ref>{{cite web|url= https://www.hollywoodreporter.com/movies/movie-reviews/milk-review-2008-movie-125079/|title= Milk Review: 2008 Movie|website= [[The Hollywood Reporter]]|date= November 2, 2008|access-date= June 12, 2024}}</ref> For his performance he was nominated for Best Actor by the [[British Academy Film Awards]], the [[Golden Globe Awards]], and the [[Independent Spirit Awards]].<ref name="Indies">{{cite news|last=Maxwell |first=Erin |url=https://www.variety.com/awardcentral_article/VR1117996677.html?nav=news&categoryid=1983&cs=1 |title=Spirit Award nominees announced |publisher=work |date=December 3, 2008 |access-date=January 23, 2009}}</ref><ref>{{cite web|url= https://www.imdb.com/name/nm0000576/awards/?ref_=nm_awd|title= Sean Penn – Awards|website= [[IMDb]]|access-date= June 12, 2024}}</ref> Penn won his second [[Academy Award for Best Actor]] and the [[Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role]].<ref>{{cite web|url= https://www.reuters.com/article/idUSTRE51M1P9/|title= Sean Penn wins best actor Oscar for "Milk"|website= Reuters|access-date= June 12, 2024}}</ref><ref>{{cite web|url= https://www.sagawards.org/awards/nominees-and-recipients/15th-annual-screen-actors-guild-awards|title= The 15th Annual Screen Actors Guild Awards|website= sagawards.org|access-date= June 12, 2024}}</ref>

In ''[[Fair Game (2010 film)|Fair Game]]'' (2010), Penn starred as [[Joseph C. Wilson]], whose wife, [[Valerie Plame]] ([[Naomi Watts]]), was outed as a [[CIA]] agent by Bush advisor [[Scooter Libby]] in retaliation for an article Wilson wrote debunking Bush's claim that Iraq was building a nuclear bomb as a rationale for invading the country. The film is based upon Plame's 2007 memoir ''[[Fair Game: My Life as a Spy, My Betrayal by the White House]]''.<ref>{{cite news|url= https://www.theguardian.com/film/2011/mar/13/fair-game-sean-penn-plame|title= Fair Game – review| newspaper=[[The Observer]] |date= March 13, 2011|access-date= June 12, 2024|last1= French|first1= Philip}}</ref> Penn reunited with [[Terrence Malick]] drama ''[[The Tree of Life (film)|The Tree of Life]]'' (2011), which won the {{lang|fr|[[Palme d'Or]]|italic=no}} at the [[2011 Cannes Film Festival]].<ref>{{cite web|url= https://variety.com/2011/film/awards/tree-of-life-wins-palme-d-or-1118037426/|title= 'Tree of Life' wins Palme d'Or|website= Variety|date= May 22, 2011|access-date= June 12, 2024}}</ref> That same year he starred in the [[Paolo Sorrentino]] directed comedy-drama ''[[This Must Be the Place (film)|This Must Be the Place]]'' (2011) opposite [[Frances McDormand]]. In the film Penn plays Cheyenne, a former rock star. The film received positive reviews<ref>{{cite web|url= https://www.rottentomatoes.com/m/this_must_be_the_place|title= This Must Be the Place|website= [[Rotten Tomatoes]]|access-date= June 12, 2024}}</ref> with Todd McCarthy of ''[[The Hollywood Reporter]]'' wrote that "Penn dominates the film, of course, although it’s a performance that slithers between the genuine and the stunt-like".<ref>{{cite web|url= https://www.hollywoodreporter.com/movies/movie-reviews/be-place-what-critics-are-385596/|title= 'This Must Be the Place': What the Critics Are Saying|website= [[The Hollywood Reporter]]|date= November 2012|access-date= June 12, 2024}}</ref>

===2012–present: Focus on directing and television roles===
In 2015, Penn starred in ''[[The Gunman (2015 film)|The Gunman]]'', a French-American action thriller based on the novel ''[[The Prone Gunman]]'', by [[Jean-Patrick Manchette]]. [[Jasmine Trinca]], [[Idris Elba]], [[Ray Winstone]], [[Mark Rylance]], and fellow Oscar-winner [[Javier Bardem]] appear in supporting roles. In ''The Gunman'', Penn played Jim Terrier, a [[sniper]] on a mercenary assassination team who kills the minister of mines of the [[Democratic Republic of the Congo|Congo]]. During this time Penn directed the drama film ''[[The Last Face]]'' (2016) starring [[Charlize Theron]] and [[Javier Bardem]] and the crime/drama film ''[[Flag Day (film)|Flag Day]]'' (2021) with [[Dylan Penn]] and [[Josh Brolin]].<ref>Sean Penn film directorial venture reviews:
*[https://movies.nytimes.com/movie/review?res=9E04E2D71539F936A25752C1A963958260 The Crossing Guard Nytimes]
*[https://www.nytimes.com/1995/11/12/movies/film-ex-bad-boy-as-sensitive-director.html Film: Bad Boy]
*[https://movies.nytimes.com/movie/review?res=9907EEDF163CF93AA25752C0A9679C8B63 The Pledge Nytimes.com]
*[https://www.smh.com.au/news/film-reviews/into-the-wild/2007/11/30/1196394599912.html Into the Wild ''Sydney Morning Herald'']
</ref> In March 2018, [[Atria Books]] published Penn's novel ''[[Bob Honey Who Just Do Stuff]].''<ref>{{cite news|url=https://www.nytimes.com/2018/03/27/books/review/sean-penn-bob-honey-who-just-do-stuff.html|title=Sean Penn, Satirist, Swings at America in a Wild Debut Novel|last=Giles|first=Jeff|date=March 27, 2018|work=The New York Times|access-date=March 28, 2018|issn=0362-4331}}</ref> After the book's release, Penn went on a highly publicized press tour.<ref>{{cite magazine |url=https://www.rollingstone.com/culture/culture-features/sean-penn-why-i-had-to-write-bob-honey-who-just-do-stuff-630210/ |title=Sean Penn: Why I Had to Write 'Bob Honey Who Just Do Stuff' |author=Diamond, Jason |date=April 4, 2018 |magazine=Rolling Stone}}</ref><ref>{{cite news |url=http://www.sandiegouniontribune.com/entertainment/books/sd-me-sean-penn-20180407-story.html |title=Sean Penn pivots from actor to novelist at La Jolla reading| author=McDonald, Jeff| date=April 7, 2018| newspaper=[[The San Diego Union-Tribune]] }}</ref><ref>{{cite news| url=https://www.latimes.com/books/la-et-jc-sean-penn-book-20180403-story.html| title=Sean Penn and Jane Smiley weren't drinking the 'Bob Honey' haterade on stage in L.A.| author=French, Agatha| date=April 3, 2018| newspaper=[[Los Angeles Times]] }}</ref> He claimed that he no longer had "a generic interest in making films", and being a writer will "dominate my creative energies for the foreseeable future".<ref>{{cite magazine| url=https://www.vogue.com/article/sean-penn-bob-honey-who-just-do-stuff-interview| title=Sean Penn on Quitting the Movie Business, His New First Novel, and #MeToo| author=Seymour, Corey| date=April 6, 2018| magazine=Vogue}}</ref>

In 2018 Penn starred in his first leading role in a television series portraying Tom Hagerty, an astronaut chosen to be one of the first people to visit [[Mars]] in the [[Hulu]] science fiction drama series ''[[The First (TV series)|The First]]'' created by [[Beau Willimon]].<ref>{{cite web|url= https://www.ign.com/videos/hulus-the-first-watch-the-exclusive-trailer-for-sean-penns-space-drama|title= Hulu's The First: Watch the Exclusive Trailer for Sean Penn's Space Drama|website= IGN|date= August 28, 2018|access-date= June 12, 2024}}</ref> Daniel Fienberg of ''[[The Hollywood Reporter]]'' wrote of his performance, "You can quickly see why Penn gravitated toward this as his series debut. His physical transformation and high-intensity confrontations...are showy, but the slowly unfolding role also lets him play quiet moments, and even light ones" adding, "It’s funny that I’m always surprised by how game Penn is to be a goofball. The guy who starred in ''[[Fast Times at Ridgemont High]]'' is still in there somewhere."<ref>{{cite web|url= https://www.hollywoodreporter.com/movies/movie-reviews/first-review-1140917/|title= The First Review|website= [[The Hollywood Reporter]]|date= September 12, 2018|access-date= June 12, 2024}}</ref> The series received positive reviews<ref>{{cite web|url= https://www.rottentomatoes.com/tv/the_first|title= The First|website= [[Rotten Tomatoes]]|access-date= June 12, 2024}}</ref> but on January 18, 2019, Hulu canceled the series after one season.<ref>{{cite web|url= https://variety.com/2019/tv/news/the-first-canceled-hulu-1203112488/|title= 'The First' Canceled at Hulu After One Season|website= Variety|date= January 19, 2019|access-date= June 12, 2024}}</ref> In 2020 Penn played himself in a cameo role in the ''[[Curb Your Enthusiasm]]'' [[List of Curb Your Enthusiasm episodes#Season 10 (2020)|season 10]] episode "The Spite Store".<ref>{{cite web|url= https://www.hollywoodreporter.com/news/general-news/curb-your-enthusiasm-boss-larry-davids-maga-hat-a-deleted-sean-penn-scene-1306538/|title= 'Curb Your Enthusiasm' Boss on Larry David's MAGA Hat … and a Deleted Sean Penn Scene|website= [[The Hollywood Reporter]]|date= August 13, 2020|access-date= June 12, 2024}}</ref>

In 2021, Penn portrayed Jack Holden, an actor based on [[William Holden]], in the [[Paul Thomas Anderson]] directed [[coming of age]] comedy-drama ''[[Licorice Pizza]]''.<ref>{{cite web|url= https://www.thewrap.com/is-licorice-pizza-based-on-a-true-story/|title= Is 'Licorice Pizza' Based on a True Story? The History Behind Paul Thomas Anderson's New Film|website= [[TheWrap]]|date= September 29, 2022|access-date= June 12, 2024}}</ref> Penn returned to television starring in the [[Starz]] political thriller limited series ''[[Gaslit (TV series)|Gaslit]]'' (2022) portraying [[John N. Mitchell]] opposite [[Julia Roberts]] as [[Martha Mitchell]]. The role required transformational prosthetics.<ref>{{cite web|url= https://variety.com/2022/artisans/news/sean-penn-julia-roberts-transformation-gaslit-starz-1235277709/|title= How Sean Penn's 'Gaslit' Transformation Came Down to an Unexpected Prosthetic|website= Variety|date= May 26, 2022|access-date= June 12, 2024}}</ref> Ben Travers of ''[[IndieWire]]'' wrote of his performance, "Penn manages to bring life to his makeup-constructed character" adding "Even his manner of speech, spitting curse words while clenching his wooden pipe, befits the boil of a man that John Mitchell becomes".<ref>{{cite web|url= https://www.indiewire.com/criticism/shows/gaslit-review-julia-roberts-starz-series-watergate-1234717204/|title= 'Gaslit' Review: Julia Roberts' Fiery Watergate Drama Sorts a Hard Truth from Many Lies|website= [[IndieWire]]|date= April 18, 2022|access-date= June 12, 2024}}</ref> For his performance he was nominated for the [[2nd Hollywood Critics Association TV Awards|Hollywood Critics Association Award for Best Actor in a Limited or Anthology Series]].<ref>{{cite web|url=https://deadline.com/2022/07/this-is-us-succession-severance-ted-lasso-2022-hca-tv-nominations-full-list-1235059982/|title=''This Is Us'', ''Succession'', ''Severance'', ''Ted Lasso'' Lead 2022 HCA TV Nominations|date=July 7, 2022|first=Denise|last=Petski|website=[[Deadline Hollywood]]|access-date=June 12, 2024}}</ref>

In 2023 Penn directed his first documentary film, ''[[Superpower (film)|Superpower]]'', profiling the [[President of Ukraine]] [[Volodymyr Zelenskyy]] which premiered at the [[Berlin International Film Festival]].<ref>{{cite news|url= https://www.nytimes.com/2023/09/18/movies/superpower-review.html|title= 'Superpower' Review: Sean Penn Chronicles the War in Ukraine|work= The New York Times|date= September 18, 2023|access-date= June 12, 2024|last1= Kenigsberg|first1= Ben}}</ref><ref>{{cite web|url= https://www.euronews.com/culture/2023/02/18/sean-penns-ukraine-documentary-superpower-premieres-at-berlin-international-film-festival|title= Sean Penn's Ukraine documentary 'Superpower' premieres at Berlin International Film Festival|website= EuroNews|date= February 18, 2023|access-date= June 12, 2024}}</ref> The film follows Penn as he travels to [[Ukraine]] to meet with Zelenskyy, the soldiers and observe firsthand how the [[Russo-Ukrainian War]] is being waged.<ref>{{cite web|url= https://www.hollywoodreporter.com/movies/movie-news/sean-penn-ukraine-war-documentary-superpower-berlin-film-festival-1235328831/|title= Sean Penn's Ukraine War Doc 'Superpower' Receives Warm Reception at Berlin World Premiere|website= [[The Hollywood Reporter]]|date= February 17, 2023|access-date= June 12, 2024}}</ref> Penn starred as a cab driver in Christy Hall's directorial debut ''[[Daddio (film)|Daddio]]'' (2023) acting opposite [[Dakota Johnson]]. Film critic Todd McCarthy of ''[[Deadline Hollywood]]'' wrote, "Sean Penn is at his absolute best here in a tremendously engaging performance as a salty working-class guy with an endless supply of opinions and ways of drawing out his passengers".<ref>{{cite web|url= https://deadline.com/2023/09/daddio-review-sean-penn-dakota-johnson-movie-christy-hall-1235536039/|title= 'Daddio' Review: Sean Penn And Dakota Johnson Drive Breakthrough First Film From Christy Hall – Telluride Film Festival|website= [[Deadline Hollywood]]|date= September 4, 2023|access-date= June 12, 2024}}</ref>