- The Chancellor Manuscript (2006) (announced) .... Peter Chancellor
- The Departed (2006) (filming) .... Billy
- The Aviator (2004) .... Howard Hughes
- Catch Me If You Can (2002) .... Frank Abagnale Jr.
- Gangs of New York (2002) .... Amsterdam Vallon
- Don's Plum (2001) .... Derek
- The Beach (2000) .... Richard
- Celebrity (1998) .... Brandon Darrow
- The Man in the Iron Mask (1998) .... King Louis XIV/Philippe
- Titanic (1997) .... Jack Dawson
- Marvin's Room (1996) .... Hank
- Romeo + Juliet (1996) .... Romeo
- ... aka Romeo and Juliet
- ... aka William Shakespeare's Romeo + Juliet (USA: complete title)
- Total Eclipse (1995) .... Arthur Rimbaud
- ... aka Eclipse totale (France: DVD title)
- ... aka Poeti dall'inferno (Italy)
- ... aka Rimbaud Verlaine (France)
- The Basketball Diaries (1995) .... Jim Carroll
- The Quick and the Dead (1995) .... The Kid
- Cent et une nuits de Simon Cinéma, Les (1995) .... Un acteur muet ŕ Hollywood
- ... aka A Hundred and One Nights
- ... aka A Hundred and One Nights of Simon Cinema
- ... aka Cent et une nuits, Les (France: short title)
- The Foot Shooting Party (1994)
- What's Eating Gilbert Grape (1993) .... Arnie Grape
- This Boy's Life (1993) .... Toby
- Poison Ivy (1992) (as Leonardo Di Caprio) .... Guy
- "Growing Pains" (1985) TV Series .... Luke Brower (1991-1992)
- Critters 3 (1991) .... Josh
- ... aka Critters 3: You Are What They Eat (USA)
- "Santa Barbara" (1984) TV Series .... Young Mason Capwell (1990)
- "Parenthood" (1990) TV Series .... Garry Buckman
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