6. 'The Aviator' (2004)
In Scorsese's expansive and lavish look at the early years of millionaire businessman/inventor Howard Hughes, DiCaprio has to blend his still-fresh faced charm with an obsessiveness that borders on madness. These are the years when Hughes was working on his delirious dogfight movie Hell's Angels, romancing Katherine Hepburn, trying to build the legendary Spruce Goose, and facing off against hostile politicians. The director connects with the man's ambition and compulsiveness, not to mention his gnawing sense of inadequacy. And DiCaprio's performance proves he's versatile as hell.