Editing Sean Penn (section)

===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>