1989
Getty Images In 1989, DiCaprio was just starting out in Hollywood with a small role as Glen in two episodes of the television show The New Lassie.
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1990
Getty Images DiCaprio landed a small role on the show The Outsiders in 1990, and was then cast as Garry Buckman on the short-lived show Parenthood. That scored him nominations for two Young Artist Awards.
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1991
Fotos International//Getty Images DiCaprio posed on the set of the popular television series Growing Pains, where he played the role of Luke Brower.
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1992
Ron Galella, Ltd.//Getty Images Looking like the definition of an early '90s teen, DiCaprio was pictured at the MTV Rock N' Jock B-Ball Pediatric AIDS Foundation.
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1993
Getty Images This was the year DiCaprio's career really picked up. First, he starred opposite Robert DeNiro in This Boy's Life, and then he played a career-defining role as the mentally handicapped brother of Johnny Depp in What's Eating Gilbert Grape.
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1994
Jim Smeal//Getty Images DiCaprio made his first appearance at the Golden Globes in January of 1994, looking adorably fresh-faced.
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1995
Catherine McGann//Getty Images DiCaprio starred in three films in 1995, the most well-known being The Basketball Diaries alongside Mark Wahlberg and Lorraine Bracco.
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1996
Frank Trapper//Getty Images This was the year DiCaprio cemented his status as a true teen heartthrob, thanks to his role in Baz Luhrmann's Romeo + Juliet. He showed up to the premiere looking slightly rumpled with then-girlfriend Kristin Zang on his arm.
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1997
SGranitz//Getty Images DiCaprio attended the Los Angeles premiere of Titanic in 1997, a role that would define his career and cause every viewer to sob publicly in a movie theater.
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1998
Getty Images In 1998, DiCaprio showed up to the 55th Annual Golden Globe Awards in a tux and slightly more tamed spiky hair.
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1999
Getty Images This was the first year DiCaprio wasn't starring in a newly released movie or show. Instead, he spent most of the year filming The Beach.
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2000
Getty Images DiCaprio gave a sweet smirk as he posed for photos at the Hollywood premiere of The Beach at Mann Chinese Theatre.
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2001
Scott Gries//Getty Images In 2001, the actor made an appearance at The Concert for New York City to benefit the victims of 9/11.
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2002
Getty Images DiCaprio secured his leading man status with two big roles in 2002: one in Martin Scorsese's Gangs of New York, the other as Frank Abagnale Jr. in Catch Me If You Can.
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2003
Tony Barson Archive//Getty Images DiCaprio looked bronzed and rocked facial hair at the Gangs of New York premiere in Paris, France.
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2004
Gregg DeGuire//Getty Images Leo has never kept his dedication to the environment out of the spotlight. Here, he attended the Dedication of NRDC's (Natural Resources Defense Council) New David Family Environmental Action Center and the Leonardo DiCaprio e-Activism Zone, encouraging visitors to learn more about environmental issues.
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2005
Getty Images In 2005, DiCaprio won his first Golden Globe award for Best Actor in a Leading Role: Drama for his role as Howard Hughes in The Aviator.
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2006
Fotos International//Getty Images DiCaprio starred in two major motion pictures in 2005: The Departed and Blood Diamond. Both scored him Golden Globe nominations for Best Actor in a Motion Picture Drama, and his Blood Diamond role got him a Best Actor nom at the Academy Awards.
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2007
Getty Images This year, DiCaprio didn't appear in any new releases, but he did spend much of early 2007 flaunting a slicked-back look on the awards show circuit.
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2008
Fotos International//Getty Images 2008 saw DiCaprio reunite with his Titanic co-star and dear friend, Kate Winslet, in Revolutionary Road, a role that got him another Best Actor nod at the Golden Globes.
Jacob is a Temporary Partnerships Editor at Hearst based in Queens, New York with his partner and cat Tiger. He loves learning and writing about Film and TV, Video Games, and the weird histories of unexpected subjects.
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