He also starred in acclaimed films such as Fight Club (1999), Babel (2006), The Assassination of Jesse James by the Coward Robert Ford (2007), Burn After Reading (2008), Inglourious Basterds (2009), The Tree of Life (2011), and The Big Short (2015).

[22] He appeared in four episodes of the CBS primetime series Dallas between December 1987 and February 1988 as Randy, the boyfriend of Jenna Wade's daughter Charlotte (played by Shalane McCall).

co-production The Dark Side of the Sun (1988) was his first leading film role, starring as a young American taken by his family to the Adriatic to find a remedy for a skin condition.

Ken Tucker of Entertainment Weekly wrote: "Pitt is a magnificent slimeball as her hoody boyfriend; looking and sounding like a malevolent John Cougar Mellencamp, he's really scary.

He played Early Grayce, a serial killer and the abusive husband of Lewis' character, in a performance described by Peter Travers of Rolling Stone as "outstanding, all boyish charm and then a snort that exudes pure menace.

"[37] Pitt also garnered attention for a brief appearance in the cult hit True Romance as a stoner named Floyd, providing comic relief to the action film.

"[42] Following the release of Interview with the Vampire, Pitt starred in Legends of the Fall (1994),[43] based on a novel by the same name by Jim Harrison, set in the American West during the first four decades of the twentieth century.

[48] In 1995, Pitt starred alongside Morgan Freeman, Gwyneth Paltrow, and Kevin Spacey in the crime thriller Seven, playing a detective on the trail of a serial killer who preys on people he considers guilty of the Seven Deadly Sins.

Janet Maslin of The New York Times called Twelve Monkeys "fierce and disturbing" and remarked on Pitt's "startlingly frenzied performance", concluding that he "electrifies Jeffrey with a weird magnetism that becomes important later in the film.

[58] Critical opinion was divided on his accent; "Pitt finds the right tone of moral ambiguity, but at times his Irish brogue is too convincing – it's hard to understand what he's saying", wrote the San Francisco Chronicle.

Paul Clinton of CNN noted the risky yet successful nature of the film,[75] while Variety remarked upon Pitt's ability to be "cool, charismatic and more dynamically physical, perhaps than [...] his breakthrough role in Thelma and Louise".

[81] The following year Pitt starred opposite Julia Roberts in the romantic comedy The Mexican,[82] a film that garnered a range of reviews[83] but enjoyed box office success.

[32] Pitt's next role, in 2001's $143 million-grossing Cold War thriller Spy Game,[32] was as Tom Bishop, an operative of the CIA's Special Activities Division, mentored by Robert Redford's character.

The film received a positive reception from critics, with The Guardian calling it "a tightly wound, slickly plotted spy comedy",[114] noting that Pitt's performance was one of the funniest.

The story follows a man who is born an octogenarian and ages in reverse,[115] with Pitt's "sensitive" performance making Benjamin Button a "timeless masterpiece", according to Michael Sragow of The Baltimore Sun.

[123] Pitt produced and appeared in Terrence Malick's experimental drama The Tree of Life, co-starring Sean Penn, which won the Palme d'Or at the 2011 Cannes Film Festival.

[124] In a performance that attracted strong praise, he portrayed the Oakland Athletics general manager Billy Beane in the drama Moneyball, which is based on the 2003 book of the same name written by Michael Lewis.

[134] Pitt starred in Fury, a World War II film directed and written by David Ayer, and co-starring Shia LaBeouf, Logan Lerman, Jon Bernthal, Michael Peña, and Jason Isaacs.

[146] A 2017 sequel to World War Z was in announced in 2016,[147] before the film was briefly delayed, then confirmed to be directed by David Fincher, and then ultimately shelved due to budget issues.

[156] In 2020, Pitt portrayed Dr. Anthony Fauci in the cold open on Saturday Night Live, earning him a Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series nomination.

Over his career he has been recognized by the Academy of Motion Picture Arts and Sciences for the following performances: Pitt visited the University of Missouri campus in October 2004 to encourage students to vote in the 2004 U.S. presidential election,[165] in which he supported John Kerry.

[171] The following year Pitt and Jolie flew to Haiti, where they visited a school supported by Yéle Haïti, a charity founded by Haitian-born hip hop musician Wyclef Jean.

[173] Along with Clooney, Damon, Don Cheadle, David Pressman, and Jerry Weintraub, Pitt is one of the founders of Not On Our Watch, an organization that focuses global attention on stopping "mass atrocities".

[174] Pitt has a sustained interest in architecture,[175] even taking time away from film to study computer-aided design at the Los Angeles offices of renowned architect Frank Gehry.

[198] In March 2012, Pitt was featured in a performance of Dustin Lance Black's play, 8 – a staged reenactment of the federal trial that overturned California's Prop 8 ban on same-sex marriage – as Judge Vaughn Walker.

[217][218] After Pitt sued Jolie for selling her share of a winery they owned to a third party, she filed a countersuit, in which she alleged that he physically and verbally abused her and their children during a plane flight in 2016.

[236] However, in July, Los Angeles superior court judge John W. Ouderkirk was removed from the case due to concerns over his impartiality as he did not sufficiently disclose business relationships with Pitt's lawyers.

[242] In December 2019, he wrote an article for Interview in which he talked with his Legends of the Fall and Meet Joe Black costar and fellow recovering alcoholic Anthony Hopkins about their experiences with addiction and recovery.

[252][253] Pitt has been frequently cited as one of the most attractive actors of all time and has been described as a sex symbol by many sources, including Empire, who named him one of the 25 sexiest stars in film history in 1995.

After Jolie was confirmed to be pregnant in early 2006, the intense media hype surrounding the couple reached what Reuters, in a story titled "The Brangelina fever," called "the point of insanity".