Brad Pitt

Singing his Praises

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."

January

Cluck for a Buck

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.

Romance Behind the Scenes

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.

October 09

Instant Legend

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."

December

Lucky Number Se7en

While filming the thriller Se7en, Pitt becomes smitten with 22-year-old costar Gwyneth Paltrow, who plays his eventually decapitated wife in the film. "They are very much in love," the film's producer Arnold Kopelson says to PEOPLE. "The chemistry between them is obvious."

December 27

Committed

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.