Leonardo DiCaprio

Higher Learning

While attending John Marshall High School in L.A., DiCaprio follows his older stepbrother, Adam Farrar, into TV commercials. He signs with an agent and does an ad for Matchbox cars at 14. Though he completes high school with a tutor, he tells the San Francisco Examiner, "life is my college."


Leonardo DiCaprio

February 20

Bum Role

After making his film debut in the campy horror film Critters 3, DiCaprio lands a recurring role as a homeless kid on Growing Pains. "I thought that on my gravestone they were going to write, 'This was the guy from Growing Pains,'" DiCaprio says in 1993. The show's star Alan Thicke requests to expand DiCaprio's role, which proves futile.


Leonardo DiCaprio

April 09

This Boy's Break

DiCaprio beats out hundreds of actors for the role of Robert De Niro's stepson in This Boy's Life. In 1996, he reunites with De Niro, who handpicks him to play a troubled teen in Marvin's Room. "He's always so compelling," costar Meryl Streep tells PEOPLE. "You can't watch anything else when he's acting."

Leonardo DiCaprio

December 17

Golden Child

Director Lasse Hallstrüm almost doesn't cast DiCaprio, 19, in What's Eating Gilbert Grape for fear his good looks might take away from the role. DiCaprio's powerful performance as a mentally-challenged teenager, opposite Johnny Depp, earns him both Golden Globe and Oscar nominations.


Leonardo DiCaprio

April 21

Dear Diary

In The Basketball Diaries, based on poet-rocker Jim Carroll's infamous journals, DiCaprio takes on the dark role of a drug addict. "It was the first script I ever read where I really felt I could go in and explore a character," DiCaprio tells Teen People.


Leonardo DiCaprio

November 01

Modern Day Tragedy

DiCaprio stars with Claire Danes in Baz Luhrmann's William Shakespeare's Romeo + Juliet makes him the Romeo of girls around the world. His penchant for models and hard-partying ways also make him a tabloid coverboy. "Scandal sells," DiCaprio tells the New York Times. "If you hear of any incident about me – a fight, a change of clothes, a little extra gel in the hair – don't believe it 'til you talk to me."


Leonardo DiCaprio

May 12

Reluctant Romeo

Although named one of PEOPLE's 50 Most Beautiful People, DiCaprio is still surprised by the female attention. "Suddenly all these teenage girls have become hysterical," he says. "What they do is shocking, climbing over walls and stuff." He makes the list again the following year, saying, "You want to be remembered for your work rather than being sort of the hunk of the month. There's always a new pretty face."

Leonardo DiCaprio

December 14

King of the World

Breaking out of teen roles and into superstardom, DiCaprio stars in Titanic with Kate Winslet. The film cost an estimated $200 million and goes on to earn more than $1.8 billion worldwide. He was initially reluctant to take on the blockbuster and the hoopla surrounding it. "Stardom may have captured his imagination for the moment," director James Cameron tells PEOPLE. "But I don't think it's where he started out, and I don't think it will be where he winds up."


March 23

And the No-Show Is...

Titanic captures 14 Academy Award nominations, but DiCaprio isn't recognized. Fans are outraged by the omission, sending hundreds of emails and calling the Academy of Motion Picture Arts and Sciences to demand a recount. DiCaprio watches on TV as Titanic wins 11 Oscars, including Best Picture. According to PEOPLE, his mother Irmelin tells reporters of his absence: "Why should he go? He wasn't nominated."

Leonardo DiCaprio

November 20

Leo Takes a Break

Fame takes its toll on DiCaprio and after parodying himself in Woody Allen's Celebrity, he takes a self-imposed, two-year acting hiatus. "I'll never reach that state of popularity again, and I don't expect to," DiCaprio tells Time. "It's not something I'm going to try to achieve either." He resurfaces in 2000 with a starring role in The Beach. Although he reportedly receives a $20 million paycheck, the film grosses less than $40 million.

Photo Credits


Edited by Julia Wang

Leonardo DiCaprio

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