60 Rare Photos of Brad Pitt Through the Years
Brad Pitt has been in the spotlight for three decades, but outside of his highly publicized romances, the world doesn't seem to know much about the man. With undoubted talent and unbeatable looks, Pitt built his stardom from the ground up. Learn more about his life and career with these rarely-seen photos through the years.
Pitt in Los Angeles before he became a household name. The actor was was raised in Springfield, Missouri by conservative Baptist parents and dropped out of college in 1986 to head west to make a name for himself.
Pitt landed his first role as "boy on the beach" in the aptly titled Hunk. He started out in the industry with uncredited walk-on roles, followed by guest appearances on sitcoms.
Pitt started dating Shalane McCall soon after moving to LA and is believed to have met McCall on the set of Dallas. It was his second-ever credited role and he played McCall's character's boyfriend, Randy, in a four-episode arc.
Pitt with then-girlfriend McCall and special guest Goofy at a benefit for terminally ill children in February 1988. Pitt was 24 and McCall was only 15 at the time.
In June 1988, Pitt stepped out with a new girlfriend, Jill Schoelen, at the Los Angeles premiere of Red Heat. The couple met on the set of Cutting Class, making it Pitt's second (but certainly not last) time he fell in love with a costar.
Pitt with Christina Applegate at an Amnesty International event. This summer evening wouldn't be their last big night out together.
In 1989, Pitt and Schoelen got engaged, but it only lasted three months. In a 2011 interview, Pitt revealed that he went to visit his then-fiancée in Budapest where she was filming a movie. When he got there, she revealed that she'd fallen in love with the director of her movie and the two called it quits. Pitt later said that Schoelen was his first big heartbreak.
Pitt appears in Head of the Class in a January 1989. Offscreen, Pitt hit it off with costar Robin Givens.
Rumors swirled that Pitt served as a rebound for Givens (right) after her public divorce from Mike Tyson. However, Givens set the record straight on Bravo's Watch What Happens Live with Andy Cohen in 2019, where she denied any romantic relationship with Pitt.
In February 1989, Pitt guest starred on season 4 of Growing Pains as Ben's favorite (albeit rude) rockstar. A season earlier, he guest starred as Carol's crush, Jeff. Oops.
Wondering why Pitt looks so glum next to the Married … With Children star? Applegate later confessed she went to the MTV Video Music Awards with Pitt, then ditched him for another guy during the show.
Pitt with Elizabeth "E.G." Daily at her album release party in September 1989. Fun fact: She's the voice behind Tommy Pickles from Rugrats and Buttercup from The Powerpuff Girls. Daily and Pitt remained close friends after dating.
Pitt appeared in an episode of Thirtysomething in October 1989. While Pitt's good looks helped him in Hollywood, he says they also affected the kinds of offers he received early in his career: "When I first got out to Hollywood they were pushing me for sitcoms, and I didn’t really have an interest in them," he told Interview in 2007. "I wanted to do films and slowly worked that way. And then it became, I guess, this curse of the leading man."
Before making it big as an actor, Pitt worked several odd jobs to get by. Entertainment Tonight reports his work ranged from dressing like a chicken to promote El Pollo Loco to acting as a chauffeur for a stripagram service.
While earning minor roles, Pitt also cashed in on his good looks and worked as a model to support himself. Here, he poses for a campaign in the early '90s.
Pitt's turn as a thieving hitchhiker who seduces Thelma (Geena Davis) in Thelma and Louise was his breakout role. "I actually read with him first—there were five candidates for the role," Davis recalled to The Hollywood Reporter in 2014. "And then he came in—this is so embarrassing—but I got a little distracted during the scene, you know? I was forgetting my lines. I was like, 'I'm totally screwing up this kid's audition.'"
Thelma and Louise helped Pitt make a name for himself due to its success at the box office. Here, he goofs around on the set of the film.
Pitt gets close to then-girlfriend Juliette Lewis at the Thelma and Louise premiere. The couple began dating when he was 27 and she was 17 and were together for three years until they split in 1993. Lewis griped to People in 2014 that most stories about her in the press are "usually about Brad Pitt or drug addiction, which hasn't been me since I was 22." Pitt has described his ex as "genius."
Michael Rapaport poses with Pitt at the Independent Spirit Awards. The comedian and Pitt were part of the ensemble cast for Quentin Tarantino and Tony Scott's 1993 hit True Romance.
One of Pitt's most notable features in his early heartthrob days was his hair, despite its often-changing color and style.
Pitt with then-girlfriend Jitka Pohlodek at the premiere of Legends of the Fall. The actor said he enjoyed making the film much more than his pervious hit, Interview with the Vampire, because he "never saw the sun" when playing the undead Louis, telling Vanity Fair that it "messed with [his] day."
The mid-nineties were huge for Pitt. His next film, Se7en, with David Fincher was another success. Pitt delivered the iconic line, "What's in the box?" in the movie.
Pitt and Gwyneth Paltrow met in 1994 on the set of Se7en and quickly became the "it" couple of Hollywood. They went on to get engaged before eventually breaking it off in 1997.
The actor attended the 53rd Annual Golden Globe Awards with Paltrow. He took home the award for Best Supporting Actor that night for Twelve Monkeys. It was Pitt's first and only Golden Globe win to date.
Pitt with his parents, William and Jane Pitt, and then-fiancée Paltrow at the premiere of The Devil's Own. Pitt and Paltrow famously had the same haircut, which she later joked about. In January 2019, the Oscar winner commented on a story saying Pitt likes to look like his girlfriends, saying, "Or we like to look like him, let's face it."
Pitt and director Jean-Jacques Annaud pose at the premiere of Seven Years in Tibet. The film's portrayal of the Chinese government resulted in Annaud and Pitt being banned from China after its release, but the Associated Press reports that Pitt returned in 2014 with then-wife Angelina Jolie.
While filming Meet Joe Black in New York City, Pitt is seen going over one of the movie's stunts during rehearsal.
Pitt cracks up Tom Cruise and then-wife Nicole Kidman in April 1998 at an event honoring the Top Gun star. Cruise and Pitt co-starred in Interview with the Vampire in 1994. In July 2019, Tarantino revealed that Cruise almost nabbed Pitt's role of Cliff Booth in Once Upon a Time in Hollywood on Josh Horowitz's Happy Sad Confused podcast.
Pitt hangs with Keith Richards and Ronnie Wood backstage at the Rolling Stones concert in Los Angeles.
Pitt and Jennifer Aniston reportedly met after Pitt had their agents set them up on a date in 1998. Here they are leaving Los Angeles' Barfly nightclub, where he threw her a massive 30th birthday party in February 1999.
Pitt and Aniston show off her engagement ring onstage at a Sting concert in November 1999 in New York City.
Even though the actor is known for his smile, most people don't know he has a chipped tooth. He told Entertainment Weekly it happened when he was in fourth grade: "I was sick. You know: big fever and delirious dreams. I passed out in the bathroom, woke up, and the tooth was chipped." He later voluntarily chipped one of his front teeth for the role of Tyler Durden in Fight Club.
Everyone's favorite celebrity couple at the time finally tied the knot in a private ceremony at their Malibu property in July 2000.
Pitt appeared on the Thanksgiving episode of his wife's hit television show in 2001. Pitt revealed in an interview that he made a mistake on his first line and the cast had to restart.
The actor, along with other celebrities, visited an Air Force base in Turkey in 2001, where they were given a tour of the equipment were able to chat with the soldiers.
Pitt and his wife, Aniston, chat with his Spy Game costar Robert Redford at the Sundance Film Festival.
Fans almost didn't recognize Pitt when he arrived at the premiere of The Bourne Identity sporting a full beard and long scruffy hair.
It was all smiles for Pitt and Aniston at the 54th Primetime Emmy Awards, where Aniston won the award for Best Lead Actress in a Comedy Series.
Pitt poses with Jim Carrey backstage at the Nickelodeon Kids' Choice Awards in April 2003. Carrey said on Chelsea Lately in 2009 that Pitt "can do no wrong."
Pitt accompanies Aniston to the premiere of her latest film, Along Came Polly.
Pitt campaigned for then-Democratic presidential candidate John Kerry at the University of Missouri in October 2004. In a speech to 1,700 students, Pitt urged them to understand the issues at hand in the November 2004 election.
The couple poses at the Primetime Emmys in September 2004, which was one of the couple's final appearances before announcing their split.
Pitt and Aniston announced in January 2005 that they were separating among rampant rumors that he and Mr. and Mrs. Smith costar Angelina Jolie were having an affair.
Pitt and Jolie make their first joint appearance to promote Mr. and Mrs. Smith at ShoWest in March 2005. The duo kept one another at arm's length for photos.
The actors were careful not to get too close on the red carpet at the Los Angeles premiere of Mr. and Mrs. Smith in June 2005 as well. Still, the then-secret couple weren't fooling anyone.
In January 2006, Pitt and Jolie announced that they were expecting, publicly acknowledging their relationship for the first time. Shiloh Nouvel was born on May 27, 2006. Here's the couple in November 2006 at the premiere of The Good Shepherd.
Pitt greets John Bul Dau, one of the stars of his 2007 documentary God Grew Tired of Us. The movie was produced by Pitt's production company, Plan B Entertainment. He started it in 2001 with his then-wife, Aniston, and business partner Brad Grey. But after their divorce, Pitt became the sole owner of the company.
While on a press tour for Ocean's Thirteen, Pitt had a handprint and footprint ceremony at Grauman's Chinese Theater in Hollywood, California.
At the premiere of Oceans 13, the final installment of the trilogy, with his costars and good friends Matt Damon and George Clooney.
Pitt and his adopted son, Pax Thien Jolie-Pitt, arrive in Venice for the film festival. The actor legally became Pax's father in 2008.
At the 61st International Cannes Film Festival, the couple announced that they were expecting twins. Knox Leon and Vivienne Marcheline were born in July. The couple also share three adopted children, meaning the twins rounded out the family to eight people in total.
The couple made it official in August 2014. They held a small, private ceremony in France with their children.
Pitt is escorted by three of his children, Pax, Shiloh, and Maddox, as well as his parents, Jane and William Pitt, to the premiere of Unbroken. The film was directed by Pitt's then-wife, Angelina Jolie.
Pitt makes a rare appearance with son Knox at the British MotoGP Grand Prix. Pitt, a longtime fan of the sport, narrated and produced Hitting the Apex, a motorcycle racing documentary.
Pitt and Jolie at an event for By the Sea, which Jolie directed and starred in with Pitt. The movie was a critical and commercial disappointment and the event would be one of the couple's final public appearances together before Jolie filed for divorce in September 2016.
In 2017, Jolie told The Hollywood Reporter's Awards Chatter podcast of the movie, "I wanted us to do some serious work together. I thought it would be a good way for us to communicate. In some ways it was, and in some ways we learned some things. But there was a heaviness, probably, during that situation that carried on, and it wasn't because of the film."
Although Pitt and Jolie's divorce seemed cut and dry, the actors entered a bitter back and forth regarding the custody and child support details of their six children in 2017, and didn't reach an agreement until November 2018.
Pitt was cast in Quentin Tarantino's highly-anticipated new film, Once Upon a Time in Hollywood, and was seen shooting scenes for the production in 2018.
Pitt shares a laugh with Once Upon a Time in Hollywood costar Leonardo DiCaprio. The duo hit it off right away, in part because, Pitt revealed to Esquire, they both got their starts on Growing Pains (though they didn't cross paths on set).
The internet went crazy when cameras caught Jennifer Aniston congratulating her ex-husband, Brad Pitt, on his SAG Award in 2020.
After being nominated for several Academy Awards over the years, Pitt finally won in 2020. He was presented the Best Supporting Actor award for his work in Once Upon a Time in Hollywood.
60 Rare Photos of Brad Pitt Through the Years
Brad Pitt has been in the spotlight for three decades, but outside of his highly publicized romances, the world doesn't seem to know much about the man. With undoubted talent and unbeatable looks, Pitt built his stardom from the ground up. Learn more about his life and career with these rarely-seen photos through the years.
Including some from before he made it big.
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