Leonardo DiCaprio's Hollywood Evolution

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.

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.

DiCaprio posed on the set of the popular television series Growing Pains, where he played the role of Luke Brower.

Looking like the definition of an early '90s teen, DiCaprio was pictured at the MTV Rock N' Jock B-Ball Pediatric AIDS Foundation.

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.

DiCaprio made his first appearance at the Golden Globes in January of 1994, looking adorably fresh-faced.

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.

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.

In 1998, DiCaprio showed up to the 55th Annual Golden Globe Awards in a tux and slightly more tamed spiky hair.

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.

DiCaprio gave a sweet smirk as he posed for photos at the Hollywood premiere of The Beach at Mann Chinese Theatre.

In 2001, the actor made an appearance at The Concert for New York City to benefit the victims of 9/11.

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.

DiCaprio looked bronzed and rocked facial hair at the Gangs of New York premiere in Paris, France.

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.

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.

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.

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.

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.