Man Crush Monday: A look back at Leonardo DiCaprio's best roles through the years

by Sarah Long
Feb 29, 2016 at 3:28 p.m. ET

After six nominations, DiCaprio finally got his Oscar. In celebration, here's a look back at his best roles.

1 /24: 'The New Lassie'

1/24 :'The New Lassie'

DiCaprio's first big break was a guest spot on the 1989 series based off the 1954 show Lassie.

2 /24: 'Parenthood'

2/24 :'Parenthood'

DiCaprio was adorable in the 1990 version of NBC's Parenthood.

3 /24: 'Critters 3'

3/24 :'Critters 3'

He made his feature film debut as Josh in this 1991 horror flick.

4 /24: 'Growing Pains'

4/24 :'Growing Pains'

DiCaprio melted hearts as Luke Brower on Growing Pains.

5 /24: 'What's Eating Gilbert Grape'

5/24 :'What's Eating Gilbert Grape'

DiCaprio got his first Oscar nomination for playing Arnie Grape in this 1993 movie.

6 /24: 'The Basketball Diaries'

6/24 :'The Basketball Diaries'

DiCaprio got a ton of attention for his 1995 performance portraying a drug-addicted teenager.

7/24 :'Romeo + Juliet'

He was completely swoon-worthy in Baz Luhrmann's 1996 version of the Shakespearean classic.

8/24 :'Marvin's Room'

DiCaprio starred alongside Hollywood heavyweights Meryl Streep and Diane Keaton in Marvin's Room.

9/24 :'Titanic'

Our hearts will go on for Jack and Rose forever.

10 /24: 'The Man in the Iron Mask'

10/24 :'The Man in the Iron Mask'

DiCaprio starred in dual roles as King Louis XIV and his imprisoned twin brother in this 1998 film.

11 /24: 'The Beach'

11/24 :'The Beach'

He played Richard in this 2000 movie about a seemingly utopian community.

12 /24: 'Gangs of New York'

12/24 :'Gangs of New York'

DiCaprio was the vengeful Amsterdam Vallon in this 2002 period film.

13 /24: 'Catch Me If You Can'

13/24 :'Catch Me If You Can'

He charmed his way through Catch Me If You Can as Frank Abagnale Jr.

14 /24: 'The Aviator'

14/24 :'The Aviator'

He earned a 2005 Best Actor in a Leading Role Oscar nod for portraying Howard Hughes.

15 /24: 'The Departed'

15/24 :'The Departed'

He played undercover cop Billy Costigan in this 2006 movie.

16 /24: 'Blood Diamond'

16/24 :'Blood Diamond'

DiCaprio got another Best Actor in a Leading Role Oscar nomination for this gut-wrenching film.

17 /24: 'Revolutionary Road'

17/24 :'Revolutionary Road'

He teamed up again with Titanic co-star Kate Winslet for this 2008 production.

18 /24: 'Inception'

18/24 :'Inception'

DiCaprio starred as Cobb in this 2010 mind-bending thriller.

19 /24: 'J. Edgar'

19/24 :'J. Edgar'

He was almost unrecognizable while portraying J. Edgar Hoover.

20 /24: 'Django Unchained'

20/24 :'Django Unchained'

He was the deplorable Calvin Candie in this 2012 Quentin Tarantino flick.

21 /24: 'The Great Gatsby'

21/24 :'The Great Gatsby'

He teamed up with Luhrmann again in 2013 to bring to life F. Scott Fitzgerald's 1925 novel.

22 /24: 'The Wolf of Wall Street'

22/24 :'The Wolf of Wall Street'

DiCaprio got another Best Actor Oscar nom for this film, which was also nominated for Best Picture.

23 /24: 'The Revenant'

23/24 :'The Revenant'

DiCaprio won Best Actor in a Leading role for his riveting portrayal of frontiersman Hugh Glass.