60 Rare Photos of Brad Pitt 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.

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 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."

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.

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.