60 Rare Photos of Brad Pitt

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1986: Moving West

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.

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1988: His First Role

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.

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1988: On-Set Romance

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.

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1988: Goofing Around

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.

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1988: New Love

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.

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1988: Famous Friends

Pitt with Christina Applegate at an Amnesty International event. This summer evening wouldn't be their last big night out together.

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1989: First Heartbreak

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.

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1989: Guest Roles

Pitt appears in Head of the Class in a January 1989. Offscreen, Pitt hit it off with costar Robin Givens.

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1989: A Rumored Romance

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1989: Growing Pains

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1989: Awards Show Date

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.

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1989: New Girlfriend

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.

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1989: More Guest Roles

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."

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1990: Odd Jobs

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.

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1990: Modeling Days

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.

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1991: Big Break

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.'"

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1991: On Set

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.

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1991: Another Love

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."

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1993: And Another Hit

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.

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1993: Signature Style

One of Pitt's most notable features in his early heartthrob days was his hair, despite its often-changing color and style.

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