Editing Sean Penn (section)

===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>