Leo DiCaprio’s 10 Most Tragic On-Screen Relationships

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Ah Leo. When it comes to love on the big screen, he simply can’t catch a break (such is life for a bona fide tragic hero). Today, he hits the big screen as Jay Gatsby, one of literature’s most iconic symbols of lovestruck despair. But when you compare it to Leo’s other roles, Gatsby doesn’t even crack the top 5. Here’s a list of the most heart-wrenching and/or calamitous love stories in Leo films. (Yes, there are spoilers below. You’ve been warned.)

10. Catch Me If You Can

Ah, the devastating taste of betrayal when the woman you love promises to elope with you, but then sets you up for a sting by the cops. Granted, when you’re a professional forger and fraud, you could chalk this up to one of the hazards of the profession.

9. The Aviator

It’s good to be Howard Hughes, particularly when it means getting to shack up with Katharine Hepburn. Alas, even the ravishing Kate can’t cure his crippling OCD, nor can she halt his wandering eye. The breakup is sweetened by the fact that Kate wound up with Spencer Tracy, and Howard with Ava Gardner.

8. Blood Diamond

Few things are sexier than a man willing to die for a worthy cause. Unfortunately for Jennifer Connelly, that’s precisely what he does.

7. The Great Gatsby

Jay Gatsby is the quintessential lovestruck fool. Yes, Daisy’s married. Yes, she’s emotionally unavailable. Yes, she ditched you while you were fighting in WWI. But why let that stop you from earning a fortune, buying a mansion next to hers, and inventing a life of extravagance, all just to get her attention? Granted, taking the blame for her vehicular homicide isn’t exactly a smart move, particularly once she goes back to her husband and leaves you to get gunned down.

6. J. Edgar

J. Edgar Hoover and Clyde Tolson were close companions and reported lovers for decades. It’s a beautiful love story, but one that was doomed by a total lack of social acceptance and an extreme case of workaholism.

5. Shutter Island

That lovely wife who tragically died in a fire? The one whose memory haunts you? Turns out you murdered her — after she’d killed your three children.

4. Inception

The trauma of having to watch your beloved leap from a 10th floor window — well, it’s enough to embed in anyone’s subconscious for a lifetime.

3. The Departed

The love scene between Leo and Vera Farmiga is one of the steamiest on film. Too bad she gets knocked up by another man — and her true love winds up with a bullet in his head (as does the father of her child).

2. Romeo & Juliet

Well, at least no one can claim the ending was a surprise.

1. Revolutionary Road

Few movies have the power to turn perfectly happy couples against each other after watching it. This is one of them.