4. Catch Me If You Can - Frank Abagnale Jr.
One of DiCaprio's first blockbuster leading roles was in this 2002 crime caper from director Steven Spielberg. DiCaprio plays Frank Abagnale, a real life con-man who's true life story inspired the film. Stemming from his teen years into adulthood, DiCaprio gives a charismatic performance as a suave, smart and talented trickster who steals millions through fraudulent cheques. On the lam from the FBI (headed by Tom Hanks) and estranged from his ne'er-do-well father (Christopher Walken), DiCaprio is able to balance his character, never allowing him to seem too innocent or guilty of his actions, all the while becoming a chameleon during his cons, posing successfully as a doctor, a lawyer and ultimately an airline pilot. Sharing the screen with Oscar winners Hanks and Walken under the direction of Spielberg is no easy feat, yet DiCaprio held his own quite well, and proved he was a leading man worth taking notice of. This was the beginning of the adult stage of his career... putting behind him the overly romantic work of the 90s.