Even as a 6-year-old choirboy, Pitt turns heads during services at South Haven Baptist Church in his hometown of Springfield, Mo. "You couldn't keep from watching Brad because his face was so expressive," piano accompanist Connie Bilyeu tells PEOPLE. "He would move his little mouth so big with all the words that he attracted everyone's attention."
Pitt drops out of the University of Missouri's journalism school to pursue acting in Hollywood. He takes a number of odd jobs once he gets there, including dressing up as an El Pollo Loco chicken and chauffeuring a limo for a strip-o-gram service.
Pitt nabs a five-episode guest-starring role on the primetime soap ''Dallas''. He plays Randy, the boyfriend of Priscilla Presley's daughter. "It was real sweaty-palms time for me," he tells PEOPLE of his first smooching scene with actress Shalane McCall. "It was kind of wild, because I'd never even met her before."
After meeting 16-year-old Juliette Lewis on the set of the TV movie Too Young to Die, they begin dating. "We were trying to be Sid and Nancy or something," he says of the relationship, which quickly gets serious when they move into a funky L.A. home together. The two, who star as greasy serial killers in 1993's Kalifornia, break up in February of that year.
Pitt steals the show as the often-shirtless hitchhiker who charms fleeing fugitive Geena Davis in Thelma & Louise. He almost didn't get the role, having been cast only when Billy Baldwin bowed out to star in Backdraft.
Often compared to Robert Redford because of his good looks, Pitt is directed by the screen legend in what the Los Angeles Times calls "a career-making performance" as one of two fly-fishing brothers in A River Runs Through It. "It's like tennis: When you play with somebody better than you, your game gets better," he tells the Chicago Tribune of working with Redford. "But yeah, it made me anxious."
In his highest-profile role to date, Pitt holds his own opposite Tom Cruise in the big-screen adaptation of Anne Rice's Interview with the Vampire. Pitt's bloodsucking character's sour mood makes shooting the movie a downer. "I hated doing this movie," he tells USA Today. "Hated it. Loved watching it. Completely hated doing it. My character is depressed from the beginning to the end."
While filming the thriller Se7en, Pitt becomes smitten with 22-year-old costar Gwyneth Paltrow, who plays his eventually decapitated wife in the film. In December 1996, Pitt proposes to Paltrow and she accepts. "I can't wait, man," he tells Rolling Stone. "...walk down the aisle, wear the ring, kiss the bride. Oh, it's going to be great." Seven months later, they call off their engagement.
PEOPLE names Pitt the Sexiest Man Alive. "Brad is one of the most attractive and talented men in the world," Vampire producer David Geffen tells PEOPLE. "He's going to be one of the biggest actors out there."
Eager to deglamorize himself, Pitt appears as a twitchy mental patient in the sci-fi thriller Twelve Monkeys. As part of his preparation, the actor checks into a psychiatric ward at a Philadelphia hospital for one day. The role earns Pitt his first Oscar nomination for Best Supporting Actor.
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