4. 'Catch Me If You Can' (2002)
In this Steven Spielberg hit, DiCaprio plays Frank Abagnale, a real-life con-man who traveled around the country and lived the high life as he impersonated pilots, lawyers, and doctors. It was an inspired bit of casting, capturing the actor right as he was transforming from fresh-faced romantic into a brooding young man — he could still play an innocent. And in the film's first half, as his character watches his parents' marriage break up, his heartbreak is palpable. By the end of the film, he's become a totally different person — a journey from kid to slightly jaded adult that's charted on Di Caprio's face.