2014

JACK & LEO

Then: His dramatic turn in the 1974 thriller Chinatown was just part of the string of big-screen moments Nicholson had on his résumé leading up to his first Oscar for One Flew Over the Cuckoo's Nest.
Now: Although DiCaprio's still waiting for an Oscar of his own, he's boosted his résumé as a scene stealer with roles in Titanic, Inception, The Departed and, more recently, he got even edgier in The Wolf of Wall Street.