Ranking Leo's Most Messed Up Characters

Looks like Leo isn't getting out of the Oscar game any time soon. On Tuesday, Deadline reported that Leonardo Dicaprio and Martin Scorsese are reuniting for The Devil in the White City. Their sixth collaboration will be an adaptation of Erik Larson's historical fiction novel about H.H. Holmes, The Devil In The White City: Murder, Magic And Madness At The Fair That Changed America. Dicaprio has wanted to play America's first serial killer Holmes for a long time; his hunting ground was the late 19th century world's fair in Chicago, but the white gleam of the city covers the sinister murder castle that Holmes has built. It's gonna be wild, and it might be the most disturbed character that DiCaprio has ever played, and that's saying something — because Dicaprio loves to play the dark and disturbed more than he loves the summertime.

There are many ways to categorize and rank the roles that DiCaprio has played, just for the sheer amount of them (even though it looks like the man is always frolicking carefree, he's been steadily making movies since he was just a babe, not to mention trying to save the world). All of his performances are solid, even the ones that end up being in categorically bad films (I think I'm the only person on earth that thinks The Beach was a good movie solely because of my Leo blinders), but, in the spirit of the dapper Chicago murderer DiCaprio is about to become on-screen, here's a ranking of the actor's most depraved and plain messed up roles.

6. Romeo from Romeo + Juliet (1996)

Messed up because the emotions on this boy, I swear. Leonardo Dicaprio’s young Romeo is a raw nerve, and it really leads him to make some bad decisions. Hindsight is 20/20, but that does nothing for DiCaprio as Romeo, because he’s like, 17 years old. Sigh. This is also the actor's saddest role. He has never sobbed tears in a more quintessentially Leo fashion than he did in Romeo + Juliet. All I’m saying is his Romeo could have benefitted from some cognitive behavioral therapy.

5. Jay Gatsby From The Great Gatsby (2013)

You can say whatever you would like about the Baz Luhrmann adaptation of what's arguably the greatest American novel of the 20th century, but DiCaprio nailed it. It's a big job to play the role of a man who's a metaphor for the sheer absurdity and impossibility of the American dream. That's pretty messed up in itself. And the actor looked great while he did it — he should dress in WASP-y summer suits all the dang time, in my opinion.

4. Howard Hughes From The Aviator (2004)

Granted, DiCaprio had a lot of material to work with here, since the eccentric aviation pioneer Howard Hughes is one tragic dude himself. But damn, he went deep into the fold with this one. Don't watch it if you don't want to see a handsome genius descend into madness, but do watch it for the costuming.

3. Amsterdam Vallon From Gangs of New York (2002)

This movie gave me nightmares, and not just because DiCaprio's long hair is so icky. He plays the late 19th century New York gangster in this Scorsese film alongside a terrifying Daniel Day-Lewis as his enemy, Bill the Butcher. He ranks high on the messed up-ed-ness list because of the sheer violence he dishes out. It's tough to see Leo that merciless.

2. Jordan Belfort From The Wolf Of Wall Street (2013)

I love a story about the ills of capitalism, and the blood, thirst, and darkness it seeps into everything around it, but even I thought that the scene where DiCaprio's Jordan Belfort crawls to the car from the porch of the country club because he's so zonked on qualades that he can't walk was a bit too much. The depravity is strong in this one.

1. U.S. Marshall "Teddy" Daniels From Shutter Island (2010)

Films that are both deeply depressing and legitimately spooky hold a special place in my heart, and Shutter Island delivers on both counts. Is there anything more terrifying and just plain screwed up about being stuck in your own brain... forever?

Honorable mention goes to Jack Dawson from the classic 1997 masterpiece Titanic; his fatal messed up flaw being, of course, that he's just too good of a guy. I don't believe there's anyone better to play America's first serial killer than America's sweetheart, Leonardo Dicaprio.

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