Leonardo DiCaprio is quite the ladies' man in Hollywood. Check out all of the star's girlfriends over the years here!

The most interesting stuff, from a historical counterfactuals point of view, pops up early, when Anderson opens by asking ...

At the time, the Oscar winner had to turn down the leading role as he was busy leading James Cameron’s ‘Titanic.’ ...

Leonardo DiCaprio opens up about turning 50, feeling 32 and his biggest regret, including not taking a role in 'Boogie Nights ...

Although Leonardo DiCaprio is beloved for playing Jack Dawson in 1997's 'Titanic', he regrets passing up on the role of Dirk ...

Oscar-winning actor Leonardo DiCaprio appears to have it all — including some regrets. The “Once Upon A Time In Hollywood” ...

Leonardo DiCaprio has made several of the most iconic movies in modern Hollywood. The actor’s numerous Oscar nominations show ...

Leonardo DiCaprio opened up to Paul Thomas Anderson for 'Esquire' about turning 50 and feeling 'emotionally' in his 30s.

Leonardo DiCaprio said his 'biggest regret' in his career was turning down Mark Wahlberg's role in 'Boogie Nights,' which he ...

Leonardo DiCaprio loves re-watching 'The Aviator' because it represents a moment of his growth in the entertainment industry.

Leonardo DiCaprio says the biggest regret of his acting career is turning down Paul Thomas Anderson's offer to star as the ...

"I just thought it was a masterpiece," the actor tells Esquire.