And this very well could be his year. When Matthew McConaughey won the Best Actor Award in 2014, Time pointed out the Academy sometimes looks at an actor's entire career rather than just an individual performance. (Video via Universal Pictures / Dallas Buyers Club)
Though, it wasn't a surprise when he won his first Oscar last year. He had been nominated for, or won, major awards throughout the season. Of those honors, he won the Desert Palm Achievement Award at the Palm Springs International Film Festival.
In the past eight years, six winners of that award went on to receive the Best Actor award at the Oscars.
Did you ever think you'd see the same person who plays Cpt. Jack Sparrow compete against this guy?
Depp has a fair shot, too. He plays Whitey Bulger, a famous Boston mobster. And the Academy loves films based on real people. (Video via Warner Bros. / "Black Mass")
And like Eddie Redmayne's portrayal of Stephen Hawking, it feels like you're watching Bulger in the film, not Depp.
All of this said, it's still a wide-open race. "The Revenant" has been kept tightly under wraps, so until critics get a look at Leo's performance, it's really any man's race to win.
This video includes images from Getty Images.