Brad Pitt’s near-40 year Hollywood career and legendary romances have generated countless headlines.
Pitt became one of Hollywood’s biggest heartthrobs and most bankable stars in the 1990s with starring roles in Legends of the Fall, Interview with the Vampire and Fight Club. At the same time, his romances with former costars Gwyneth Paltrow, Geena Davis and Juliette Lewis put his private life under intense scrutiny. Pitt married Friends star Jennifer Aniston in July 2000, but they divorced only five years later.
While Pitt was going through his divorce, he was photographed on outings with his Mr. & Mrs. Smith costar Angelina Jolie. (Both have denied their romantic relationship overlapped with Pitt and Aniston’s marriage.) Jolie and Pitt were married in 2014, yet a bitter divorce battle ensued once the couple split in 2016. Jolie and Pitt finally settled their divorce in 2024, more than eight years after they originally separated.
A source exclusively told Us Weekly in June 2025 that Pitt had “embraced” a quieter lifestyle following his divorce.
“He likes a slower [pace] now,” the insider added.
Scroll down to see photos of Pitt through the years:
‘Thelma and Louise’
The Shawnee, Oklahoma native was born in December 1963 to trucking company owner William Alvin Pitt and school counselor Jane Etta Hillhouse. The Pitts moved to Springfield, Missouri when Pitt was a boy and he was raised in a deeply religious family.
Pitt left the University of Missouri a few credits shy of graduating in order to pursue acting in the mid 1980s. A few uncredited appearances in Charlie Sheen’s 1987 crime drama No Man’s Land and the Robert Downey Jr. drama Less than Zero followed, until Pitt eventually started building up his resume with guest appearances on TV sitcoms like Another World and Growing Pains.
His true breakout role was in the 1991 comedy crime caper, where he played a hitchhiking hustler opposite Susan Sarandon and Geena Davis.
Pitt recalled to W Magazine that he knew he was “the guy” for Thelma & Louise immediately, though the producers weren’t quite so sure.
“They went through a couple of other actors,” he said. “I didn’t get the part at first, and then it came back around and I didn’t get it again, and I went, ‘Huh. All right. Moving on.’ And then it came back around again. I feel like it was three times.”
Dating Geena Davis
Pitt was linked to his Thelma & Louise costar around the time they made the Oscar-winning movie. He looked back on filming Thelma & Louise’s legendary love scene with Davis during a 2013 profile for W Magazine.
“Geena was so sweet and kind and delicate,” he remembered. “That love scene, I think, went on for two days of shooting. She took care of me.”
Juliette Lewis Relationship
Former child star Lewis dated Pitt after they worked together on the 1990 TV movie Too Young to Die?. They reunited as a modern day Bonnie and Clyde in 1993’s crime thriller Kalifornia.
Following the couple’s breakup in the mid 1990s, Pitt told Vanity Fair that he “still loved” his ex-girlfriend.
“There’s some real genius there,” he added. “I had a great time with her. It was one of the greatest relationships I’ve ever been in. The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?”
‘Interview With the Vampire’
A timeless screen pairing of ‘90s heartthrobs, Pitt and Tom Cruise propelled the 1994 adaptation of author Anne Rice’s vampire novel to more than $220 million at the box office.
The leading men reunited in 2025 for F1’s red carpet premiere, where Pitt teased that they may work together again when Cruise “does something again that’s on the ground.”
“I’m not gonna hang my ass off airplane [and] s*** like that,” Pitt told E! News in June 2025, in reference to Tom’s notoriously high stakes stunts.
‘Legends of the Fall’
In 1995, Pitt received his first Golden Globe nomination for his depiction of the heroic adventurer Tristan Ludlow in Legends of the Fall. (He lost the Best Actor Globe to Tom Hanks for Forrest Gump.)
While Pitt reached a new career peak with Legends of the Fall, director Ed Zwick wrote in his memoir, Hits, Flops, and Other Illusions: My Fortysomething Years in Hollywood, that the actor considered quitting the movie. Zwick and producer Marshall Herskovitz eventually convinced Pitt to remain on board.
“When I showed Brad the final film, he wasn’t pleased. He felt I’d underplayed his character’s madness,” the filmmaker wrote. “I had in fact cut only a single shot from the scene where Tristan is raging with fever, screaming as the waves wash over him on the schooner. But it was a shot he dearly loved, and it would have been little enough to leave it in, and I should have. Apologies, Brad.”
1st Golden Globe win
One year after coming up short at the Globes, he won Best Supporting Actor for his off-kilter portrayal of mental patient Jeffrey Goines in the post apocalyptic thriller 12 Monkeys.
“I’d like to thank the makers of [diarrhea medication] Kaopectate,” Pitt joked in his acceptance speech. “They’ve done a great service for their fellow man!”
Gwyneth Paltrow Relationship
Following his split from Juliette Lewis, Pitt’s next great romance was with his Se7en costar, Paltrow. Pitt and Paltrow’s relationship coincided with their careers ascending between 1994 and 1997, thereby making them Hollywood’s “It Couple” for the era.
“He’s a very intriguing character,” Paltrow said of Pitt in a March 2025 interview with Vanity Fair. “It’s like having dated, I don’t know, Prince William or something. That’s always going to come up.”
‘Fight Club’
Pitt strayed from his usual romantic leading roles as the twisted Tyler Durden, opposite Edward Norton, in 1999’s Fight Club. While Fight Club is regarded as a cult classic today, Pitt recalled a disastrous early screening at the Venice Film Festival.
“First joke comes up and it’s just crickets. It’s dead silence,” he said on the “WTF with Marc Maron” podcast in 2020. “And another joke and it’s just dead silence. This thing is not translating. Subtitles, it is not translating at all. The more that happened, the funnier it got to Edward and I and we just start laughing. So, we’re the assholes in the back laughing at our own jokes. The only ones!”
‘Ocean’s Eleven’
Pitt kicked off the 2000s as part of the ultimate heist squad, alongside George Clooney, Matt Damon, Julia Roberts and Don Cheadle, for a remake of the 1960 Rat Pack movie Ocean’s Eleven. Three sequels followed and there have been rumblings in recent years that Ocean’s Fourteen could finally happen.
“The problem is I’d have to then work with Clooney, and I’ve kind of sworn that off for health reasons,” Pitt joked to E! News in June 2025. “But if that were to happen, I do know that there is a script out there that Mr. Clooney has developed, and it’s pretty damn tasty.”
(Pitt and Clooney remain close friends and collaborators, having most recently worked together on the 2024 comedic thriller Wolfs.)
Jennifer Aniston Marriage
The Friends star started dating Pitt in 1998 and they married two years later in a private ceremony in Malibu. Their marriage lasted until January 2005 when the couple announced in a joint statement that they were going their separate ways. (Pitt and Aniston finalized their divorce in October 2005.)
“We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration,” the couple said in a statement to multiple outlets. “We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.”
Starring in ‘Mr and Mrs. Smith’ with Angelina Jolie
Pitt and Jolie embarked on a hugely-publicized romance while filming 2005’s Mr. & Mrs. Smith, though both have insisted there was no overlap with the end of Pitt’s marriage to Aniston.
“To be intimate with a married man … is not something I could forgive,” she said in May 2005. “I could not, could not look at myself in the morning if I did that.”
‘The Curious Case of Benjamin Button’
Pitt reunited with Fight Club director David Fincher for, possibly, his greatest acting challenge yet in 2008’s The Curious Case of Benjamin Button, in which he played a man aging in reverse. The latter stages of the film used CGI to depict Pitt’s title character literally devolving into a baby.
“If you were attempting a film like this [in the past], you would have to plug in different actors or different ages … to … just to perform the thing,” Pitt told CBS News at the time. “And … it always, I mean, becomes disjointed. Sometimes it connects, sometimes it doesn’t. Sometimes the actors kinda look alike. But they seldom have the same kind of personality, or verve, or even dignity.”
He went on, “In this … we, for the first time, got an opportunity to play the character from childhood to death, from birth to old age, or, in my case, from old age, which was still young, to birth. And, we got to drive the performance all the way. It was an … incredible luxury. It’ll become the norm. Right now, it’s a luxury.”
Pitt received a Best Actor Oscar nomination for Benjamin Button, though Sean Penn won for Milk.
‘Inglourious Basterds’
Pitt’s fruitful working relationship with director Quentin Tarantino continued with 2009’s Inglourious Basterds, an fictionalized retelling of World War II centered around Jewish American soldiers waging a brutal campaign of revenge against the Nazis.
“[Tarantino] writes everything by hand, he writes single-spaced on a manila pad,” Pitt revealed at the Santa Barbara International Film Festival in 2020. “He over-writes and over-writes, and once he has the script, he gives it to you with his famous cover page, which is in handwriting … ‘Basterds’ was originally misspelled, and because that’s the way he originally wrote it, that’s the way it went on the marquee.”
Marriage and Family With Angelina Jolie
The couple balanced their busy careers with family obligations and Jolie’s growing profile as a United Nations special envoy throughout the 2000s. Pitt and Jolie announced their engagement in April 2012 after seven years together.
“[The engagement is] confirmed,” their spokesperson said at the time. “It is a promise for the future, and their kids are very happy. There’s no date set at this time. Brad designed the ring.”
They tied the knot at their winery, Château Miraval, in France in August 2014. The couple share six children together: they adopted Maddox, Zahara, and Pax and biologically welcomed Shiloh, Knox and Vivienne.
Divorce and Abuse Allegations
Hollywood was stunned when Jolie filed for divorce in September 2016, citing “irreconcilable differences” as the cause of their split. It later came to light that Pitt was under federal investigation for allegedly being “verbally abusive” and getting “physical” with one of his children on board their private jet in 2016.
An unsealed federal investigation report obtained by NBC News in 2022 indicated that the “husband allegedly physically and verbally assaulted plaintiff and the children, who have experienced lasting physical and mental trauma as a result of the assault.” (Pitt and Jolie were not named directly in the report.)
Brad Pitt and Angelina Jolie have been locked in a messy court battle ever since she filed for divorce in September 2016, but the pair were not always at odds. The Oscar winners allegedly fell for each other while filming the 2005 action film Mr. & Mrs. Smith. The origination of their relationship instantly caused […]
NBC reported that the FBI decided not to move forward with criminal charges with the consent of “all parties” and “all law enforcement.”
Pitt has denied any wrongdoing, but has never publicly spoken about the situation in detail. He did release a brief statement following Jolie filing for divorce.
“I am very saddened by this, but what matters most now is the well-being of our kids,” Pitt said. “I kindly ask the press to give them the space they deserve during this challenging time.”
Pitt and Jolie spent the next eight years fighting in court before finally reaching a divorce settlement in December 2024.
“More than eight years ago, Angelina filed for divorce from Mr. Pitt. She and the children left all of the properties they had shared with Mr. Pitt, and since that time she has focused on finding peace and healing for their family,” Jolie’s lawyer James Simon told Us at the time. “This is just one part of a long ongoing process that started eight years ago. Frankly, Angelina is exhausted, but she is relieved this one part is over.”
The former couple are set to face off in court once again in summer 2025 over the French winery they purchased while married.
Sobriety
Brad Pitt in June 23, 2025. Samir Hussein/WireImage
Pitt has said that he made the decision to get sober shortly after splitting from Jolie. He has spoken frequently about how attending AA meetings with other men allowed him to be more vulnerable.
“I just thought it was just incredible, men sharing their experiences, their foibles, their missteps, their wants, their aches, and a lot of humor with it. I thought it was a really special experience,” he explained on Armchair Expert in June 2025.
Pitt continued, “I was pretty much on my knees, and I was really open. I was trying anything and everyone. Anything anyone threw at me. It was a difficult time. I needed rebooting. I needed to wake the f*** up in some areas. And it just meant a lot to me.”
He went on, “When I’ve stepped in s***, I’m pretty good at taking responsibility for it and owning up to it. And now it’s a quest to, you know, ‘What do I do with this? How can I right this?’ And make sure it doesn’t happen again.”
Oscar Win
Pitt received his first Academy Award for acting in 2020 for his depiction of down-on-his-luck Hollywood stunt double Cliff Booth, opposite Leonardo DiCaprio, in Tarantino’s hit Once Upon a Time in Hollywood. (Pitt previously received an Oscar for producing Best Picture winner 12 Years a Slave in 2014.)
“Leo, I’ll ride on your coattails forever. The view is fantastic,” Pitt joked in his Best Supporting Actor acceptance speech.
Pitt, DiCaprio and Tarantino are expected to team up again for a Netflix streaming sequel to Once Upon a Time in Hollywood.
Hitting the Track in ‘F1’
Pitt teamed up with Top Gun: Maverick director Joseph Kosinski on 2025’s F1, which casts him as a former Formula One driver coming out of retirement to coach an unproven rookie (Damson Idris). Prior to the blockbuster’s release, Pitt said he relished the chance to embed with real Formula One pit crews to research his role.
“For me, it was just a no-brainer when [Kosinski] had this audacious plan to embed us in the racing season, to put us actually in the cars. It was just a dream come true,” Pitt said at a Mexico City press conference in June 2025. “I’ve been trying to do a racing film for literally decades. And whether it was on bikes or whether it was in cars, for whatever reason, it just didn’t pan out. I’m so grateful because the experience Joe gave us, putting us in the car, putting us in this ecosystem of the F1 racing season, with all the drivers, with the teams, was just an extraordinary experience.”
Ines de Ramon Relationship
Brad Pitt and Ines de Ramon in June 2025. Gareth Cattermole/Getty Images for Warner Bros. Pictures
Pitt has been dating jewelry designer Ines de Ramon since 2022. He told Access Hollywood in June 2025 that he was thankful to have de Ramon’s support at this stage in his life.
“It takes two,” he lovingly declared.
