Friday, December 26, 2025

Brad Pitt’s Hollywood Career: Major Roles, Dating Highs and Lows, Divorce Drama & His Life Now

Brad Pitt‘s Hollywood career and relationships have made headlines for nearly four decades, tracing his rise from a young actor to a global icon, with public interest in both his films and personal life remaining intense since the 1990s. From his early breakout roles and high-profile romances to his recent quieter lifestyle, Pitt’s story is defined by major career achievements and ongoing media fascination with his relationships.

Early Life and Starting Out in Acting

Born in Shawnee, Oklahoma in December 1963 to William Alvin Pitt, a trucking company owner, and Jane Etta Hillhouse, a school counselor, Brad Pitt spent his childhood in Springfield, Missouri where his family relocated. Raised in a deeply religious household, he attended the University of Missouri but left just shy of graduating to pursue acting in the mid-1980s. Pitt began building experience with uncredited film parts and television sitcom guest roles, including on Another World and Growing Pains.

Breakthrough with ‘Thelma & Louise’

Pitt’s ascent started with his 1991 performance as a charismatic hitchhiker in Thelma & Louise, acting alongside Susan Sarandon and Geena Davis. While recalling getting the part, Pitt shared the uncertainty of the casting process:

“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.”

—Brad Pitt, Actor.

Connections and Romance with Geena Davis

During the making of Thelma & Louise, Pitt was romantically linked to co-star Geena Davis. On filming their famous love scene, he reflected:

Brad Pitt
Image of: Brad Pitt

“Geena was so sweet and kind and delicate,”

Pitt remembered.

“That love scene, I think, went on for two days of shooting. She took care of me.”

—Brad Pitt, Actor.

Juliette Lewis: Relationship and Film Collaboration

Pitt dated Juliette Lewis following their work together in the 1990 TV movie Too Young to Die? and reunited in 1993’s Kalifornia. After their mid-1990s split, Pitt discussed the relationship:

“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?”

—Brad Pitt, Actor.

Major Roles and Hollywood Stardom in the 1990s

Pitt’s status grew rapidly in the 1990s, landing lead roles and gaining recognition. In 1994, he starred with Tom Cruise in Interview with the Vampire, based on Anne Rice’s novel. The two actors recently appeared together at the 2025 F1 red carpet premiere, where they hinted at collaborating in the future, with Pitt joking,

“I’m not gonna hang my ass off airplane [and] s*** like that,”

referring to Cruise’s daring stunts. —Brad Pitt, Actor.

In 1995, Pitt received his first Golden Globe nomination for portraying Tristan Ludlow in Legends of the Fall, although he did not win. Director Ed Zwick described challenges during filming, noting,

“When I showed Brad the final film, he wasn’t pleased. He felt I’d underplayed his character’s madness,”

Zwick 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.”

—Ed Zwick, Director.

First Golden Globe Victory and Comic Roles

Pitt won his first Golden Globe for Best Supporting Actor in 1996 for his performance as Jeffrey Goines in 12 Monkeys. His acceptance speech reflected his humor:

“I’d like to thank the makers of [diarrhea medication] Kaopectate,”

Pitt joked,

“They’ve done a great service for their fellow man!”

—Brad Pitt, Actor.

High-Profile Romance with Gwyneth Paltrow

Shortly after breaking up with Juliette Lewis, Pitt began dating his Se7en co-star Gwyneth Paltrow, making them one of the 1990s’ most talked-about couples. Their relationship, which coincided with both stars’ career upswings, lasted until 1997. Paltrow reflected years later,

“It’s like having dated, I don’t know, Prince William or something. That’s always going to come up.”

—Gwyneth Paltrow, Actor.

Transition to Cult and Mainstream Success

By the late 1990s, Pitt took on more challenging and unconventional roles. His turn as Tyler Durden opposite Edward Norton in 1999’s Fight Club is now seen as a cult favorite. On early screenings, Pitt recalled,

“First joke comes up and it’s just crickets. It’s dead silence,”

he said.

“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!”

—Brad Pitt, Actor.

The ‘Ocean’s’ Franchise and Friendships

The 2000s marked Pitt’s move into the blockbuster Ocean’s franchise alongside George Clooney, Matt Damon, Julia Roberts, and Don Cheadle. The films were critical and commercial hits, and rumors persist about a potential Ocean’s Fourteen installment. Pitt commented on the idea,

“The problem is I’d have to then work with Clooney, and I’ve kind of sworn that off for health reasons,”

he joked.

“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.”

—Brad Pitt, Actor. Pitt and Clooney continued their collaboration in 2024’s Wolfs.

Marriage to Jennifer Aniston

Pitt began dating Friends star Jennifer Aniston in 1998, marrying her in a private Malibu ceremony in 2000. Their relationship was closely followed in the media, and when they separated in January 2005, they released a joint statement:

“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.

“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.”

—Brad Pitt & Jennifer Aniston, Actors.

New Beginnings with Angelina Jolie

Pitt’s next major relationship was with Angelina Jolie, his co-star in 2005’s Mr. & Mrs. Smith. Their romance attracted significant attention, especially as both maintained that their relationship began after Pitt’s marriage to Aniston had ended. Jolie publicly stated her boundaries:

“To be intimate with a married man … is not something I could forgive,”

she said in 2005.

“I could not, could not look at myself in the morning if I did that.”

—Angelina Jolie, Actor.

Critical Acclaim: ‘The Curious Case of Benjamin Button’ and Awards Season

The late 2000s saw Pitt reunite with director David Fincher for The Curious Case of Benjamin Button, a role requiring extensive CGI as his character aged in reverse. Pitt described the experience:

“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.

“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.”

—Brad Pitt, Actor. He continued,

“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.”

—Brad Pitt, Actor. The performance earned Pitt an Oscar nomination, though Sean Penn ultimately won for Milk.

Collaborations with Quentin Tarantino

Pitt has frequently teamed with director Quentin Tarantino, most notably in Inglourious Basterds, a revisionist World War II story. Discussing Tarantino’s methods, Pitt shared:

“[Tarantino] writes everything by hand, he writes single-spaced on a manila pad,”

Pitt revealed.

“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.”

—Brad Pitt, Actor.

Marriage, Family, and Philanthropy with Jolie

Pitt’s life with Jolie included balancing active film careers, parenting, and philanthropy, with Jolie expanding her role as a United Nations special envoy. Their 2012 engagement was announced formally: “[The engagement is] confirmed,” their spokesperson said.

“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.”

—Pitt and Jolie Spokesperson. They married in France in 2014 at Château Miraval and share six children—three adopted (Maddox, Zahara, Pax) and three biological (Shiloh, Knox, Vivienne).

Divorce, Legal Battles, and Allegations

In September 2016, Hollywood was shocked when Jolie filed for divorce, citing irreconcilable differences. Afterward, reports surfaced of a federal investigation into Pitt for alleged verbal and physical abuse of their children on a private jet, without directly naming Pitt and Jolie in official documents:

“husband allegedly physically and verbally assaulted plaintiff and the children, who have experienced lasting physical and mental trauma as a result of the assault.”

—Federal Investigation Report. Authorities ultimately took no legal action, and Pitt has denied any wrongdoing, stating publicly after the separation,

“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.”

—Brad Pitt, Actor.

The divorce and subsequent custody battles stretched over eight years, with Jolie’s attorney James Simon remarking at the settlement,

“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,”

Simon told Us Weekly.

“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.”

—James Simon, Attorney.

The two remain embroiled in legal disputes over their French winery, Château Miraval, with a court case scheduled for summer 2025.

Personal Transformation and Sobriety

Amid the fallout of his marriage to Jolie, Pitt turned to sobriety, attending Alcoholics Anonymous meetings. He spoke about the experience:

“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. —Brad Pitt, Actor. Reflecting on that period, Pitt added,

“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.”

—Brad Pitt, Actor. He also commented on growth and accountability:

“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.”

—Brad Pitt, Actor.

Oscar Win for ‘Once Upon a Time in Hollywood’

Pitt achieved career recognition with his first acting Oscar in 2020, winning Best Supporting Actor for his role as Cliff Booth in Quentin Tarantino’s Once Upon a Time in Hollywood, alongside Leonardo DiCaprio. In his acceptance speech, Pitt playfully acknowledged his co-star:

“Leo, I’ll ride on your coattails forever. The view is fantastic.”

—Brad Pitt, Actor. Pitt’s collaboration with Tarantino and DiCaprio is set to continue with a planned Netflix sequel.

Recent Projects and the Making of ‘F1’

Pitt recently teamed up with director Joseph Kosinski for F1, released in 2025, where he plays a former Formula One driver coaching an emerging talent, portrayed by Damson Idris. Pitt found the experience of training with professional pit crews both challenging and inspiring. At a Mexico City press conference, he said,

“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.

“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.”

—Brad Pitt, Actor.

Private Life After Divorce and Current Relationship

Since finalizing his divorce, Pitt’s lifestyle has changed significantly. A source explained in June 2025,

“He likes a slower [pace] now,”

the insider explained. Pitt is currently in a relationship with jewelry designer Ines de Ramon, having reportedly started dating in 2022. During a 2025 interview, Pitt expressed appreciation for her support and partnership. He summed up the importance of companionship by saying, “It takes two,” —Brad Pitt, Actor.

Enduring Influence and What Lies Ahead

Brad Pitt’s lasting influence in the film industry is evident through a range of critically acclaimed performances, evolving artistic choices, and persistent public interest in his personal life. As he continues to take on new roles and navigate ongoing legal matters, his story remains a focal point in pop culture and Hollywood history, with particular attention on how Brad Pitt’s Hollywood career and relationships intersect and evolve over time.