1. 1660s: The Man in the Iron Mask
As Louis XIV, badass king of France.
2. 1850s: Django Unchained
As Calvin Candie, the owner of a plantation called Candyland.
3. 1860s: Gangs of New York
As Amsterdam Vallon, who returns home to seek revenge on the man who killed his father.
4. 1880s: The Quick and the Dead
As “The Kid,” a participant in a gun duel.
5. 1910s: Titanic
As Jack Dawson, the vagrant who finds love on the sinking Titanic.
6. 1920s: The Great Gatsby
As the rich Jay Gatsby.
7. 1920s-1940s: The Aviator
As Howard Hughes, based on the real-life American aviator and film director.
8. 1950s: Revolutionary Road
As Frank Wheeler, one half of a frustrated suburban couple.
9. 1950s: Shutter Island
As U.S. Marshal Teddy Daniels who is trying to hunt down an escaped mental patient.
10. 1950s: This Boy’s Life
As Toby Wolff, a young boy living with his kind of insane mother and scary stepdad.
11. 1960s: Catch Me If You Can
As Frank Abagnale Jr., a con artist who fakes being a pilot.
12. 1990s: Basketball Diaries
As Jim Carroll, a high school basketball star who struggles with drug addiction.
13. 2000s: The Departed
As Billy Costigan, an undercover cop investigating the mob.
14. The Leonardo DiCaprio role timeline…
Featuring his more epic, historical roles.