A History Of Leonardo DiCaprio's On-Screen Romantic Fails

This weekend Leonardo DiCaprio and Baz Luhrmann's anticipated update of The Great Gatsby finally drops after being delayed since last winter. It's not the first time the Australian filmmaker has updated a classic story with Leo in the lead, but we noticed another recurring trend as well: This isn't Leo's first time portraying one half of a doomed love affair. In fact, it's his fifteenth.

Despite being the leader of New York City's own "Pussy Posse" and boasting one of the most impressive dating histories in recent memory, on the silver screen the Cap just can't win. Star-crossed romances, literary and historic characters who have been lames in love—he's played them all and then some.

In celebration of his performance as one of pop culture's most infamously doomed characters, Complex has compiled a comprehensive history of each and every one of Leonardo's on-screen love disasters. Click through for A History of Leonardo DiCaprio's On-Screen Romantic Fails.

Written by Frazier Tharpe (@The_SummerMan)

Fail Level: High

In which Leo portrays real-life 19th century poet Arthur Rimbauld, who embarked on a torrid four year affair with Paul Verlaine, a fellow poet twice his age. Bratty, rebellious teenager shacking up with a married man who’s pushing 40? The day-to-day of this relationship went about as well as it ended, which is to say, disastrously.

The odd couple eventually fall into a sado-masochistic pattern of constant berating and bursts of violence, as they slide farther and farther down the social ladder, eventually living in near-poverty. And how does this star-crossed romance come to an end? With Paul doing a skid bid for firing multiple bullets at Arthur (he caught one in the wrist).

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Fail Level: Simp Fatality

Before taking on the most famous simp fatality in American literature, Leo and Baz united for the first time in 1996 to tackle the most famous one in all of literary history. We know how this one goes, but while the young lovers’ devotion to each other is beautiful and all, Romeo still fails here because Juliet wasn't actually dead. Again, she is not dead.

If dude was just a few seconds slower in making the ultimate declaration, these two could've been riding off into the sunset. Alas, they’re just two beautiful corpses.

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Fail Level: Simp Fatality

Don’t get us wrong, Jack Dawson executed several noteworthy wins here. Bagging the rich girl, scoring a vacation hookup, and engaging in some steamy car sex. Then that iceberg fracas pops off, which is one hell of a cock-block, and before you know it these two are left afloat in the bitter cold. Except, Jack romantically, bravely lets Rose take refuge on a floating door while he chills in the water, literally. Why couldn't they both fit? Jack is chivalrous beyond common sense here, despite all the tweens who begged to disagree—all the way to the box office.

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Fail Level: Obsessive Creep

As the arrogant, manipulative King Louis XIV, Leo’s thirst for the already-spoken-for Christine Bellefort is unparalleled. He sends her lover off to die in the war, he even drops a few royal bands on health care for her family. Solid sociopath seduction moves, with a high guarantee for success—until a pre-mortem letter from Christine’s late lover halts Louis’s advances. Dude loses out to a letter, from a dead guy, before driving Christine to suicide. Talk about a royal fuck-up.

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Fail Level: Extremely high

Despite an in media res introduction that offers little in the way of exposition, it’s not hard to tell what’s going on here. Leo’s portraying Hollywood heartthrob Brandon Darrow (very meta), who is clearly embroiled in a not-so-healthy relationship, as evidenced by subtle clues like his complete “redecoration” of a hotel room while he screams love/hate profanities at his paramour, or her repeatedly shrieking “he tried to throw me out of the window.”

Then she calls security and it looks like it’s over for these two crazy kids—until a long elevator ride heals all. She decides not to press charges! Hallelujah. The impression gleaned from the day-in-the-life presentation of these scenes: They both engage in this kind of fuckshit on the regular.

Fail Level: Low

Richard’s vacation romance with a hot young French thing in the idyllic, secret beach community is ruined when the leader, played by Tilda Swinton, gets dirt on him and offers her silence for sex. Copulating with Swinton against his will is punishment enough, but chasing the main piece away as a result really compounds this into a heavy loss.

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Fail Level: High

It’s clear from the moment Frank Abagnale strikes up a relationship with Brenda that the (moderately) innocent young love is doomed. Why? Because Frank is guilty of multiple fraud schemes, a fugitive of the law currently masquerading as a doctor. Viewers expect the tenacity of FBI agent Carl Hanratty to Frank to run out on her sooner or later.

And yet! Turns out Brenda is the betrayer; she willingly goes along with an ambush plot after Frank fesses up and makes plans to bring her along the lam. Frank escapes the dragnet, but it’s clear that Brenda cut him deep, cut him like surgery.

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Fail Level: Obsessive Creep

Howard Hughes dated some fine women, given that he devolved into an OCD-addled recluse. But while dating around with the likes of Katherine Hepburn and Ava Gardner are unquestionable wins, the borderline psychotic ways in which he kept tabs on them is not. If you've gotta resort to phone taps and a goon squad shadow team, maybe it’s time to call it quits and move on, bruh bruh.

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Fail Level: Moderate

This one isn’t actually Leo’s fault. Admittedly, any relationship that starts with the anti meet-cute that is Billy Costigan and Dr. Madolyn’s hilariously awful therapy session is doomed, no question. But throughout the film, there’s a lustful undercurrent to the unofficial, café-set sessions that follow, and they slowly evolve from doctor-patient, to friends, to one-time lovers. Madolyn’s clearly interested but she’s already spoken for, leaving Billy in a solid position as the next guy in-line as soon as her current beau fucks up.

And does he ever, since her man happens to be Colin Sullivan, the rat bastard mob mole planted within the Boston police department. In a brighter film, Colin would've been disgraced and rotting in jail while Billy rides off into the sunset with his girl (and child?). Alas, beware the Costello outfit’s conveniently planted third man.

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Fail Level: Fatally high

The emptiness of suburban domesticity and the illusion of the American dream are personified in the slow but deliberate dissolution of the Wheeler marriage. Leo and Kate Winslet just can’t seem to make it work on-screen, can they? But whereas their love in Titanic endured, even after death, their marriage here is systematically defeated by gradually mounting bitterness and failed expectations.

By the time infidelity and an unwanted pregnancy enter the picture, the Wheelers have become emotional zombies going through the motions of a marriage that’s already dead. And then April Wheeler attempts a DIY abortion, and dies for real. If they only went to Paris—actually, nevermind. Things probably would’ve fallen apart anyway.

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Fail Level: Mentally Unstable

How badly does a marriage have to end to send a guy into a delusional fantasy state to cope? How about one that ends with husband murdering wife (Michelle Williams) because she went nuts and killed their three kids? Leading into the biggest question of them all: What the hell did Andrew even see in this chick to begin with?

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Fail Level: Mentally Unstable

The dream is real, and so is the fail. There’s being hung up on an ex, and then there’s the so-unhealthy-it-can’t-be-defined state of stuck that Dom Cobb finds himself in during Inception.

He repeatedly puts the whole squad in jeopardy because he just can’t stop letting his wife, aptly named Mal (Marion Cotillard)—or rather the projection of his guilt over what he did to her—in to crash the party, i.e. ruining his own best laid plans. He'd rather spend his nights in dream-ville hanging with memories of Mal instead of, say, capitalizing on the obvious crush protégé Ariadne has on him.

And then there’s the reason he feels so guilty to begin with, the biggest fail of all: his not so genius plan to get Mal to realize they were literally living a dream. Which backfires spectacularly when the idea still has a hold on her in reality, leading to her suicide. It's such a colossal, trainwreck of a fuck-up that dude has to go to the depths of his psyche to work through it.

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Fail Level: High

Hoover and Tolson (Armie Hammer) are both in love with the other, yet both too chicken to even try and carry on in secret. As for Hoover’s luck with the ladies, well, there’s that supremely cringe-worthy scene in the first act where he proposes to his future secretary, Helen Gandy, after she already denied him a kiss. In the shock of all shocks, J. Edgar Hoover died as he lived—alone.

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Fail Level: Moderate

Yes, we realize Calvin Candie doesn’t have a love interest in Django, save for the demure lady seated on the couch in his Mandingo fight room, who's basically anonymous. Which is precisely why Calvin's love life is a fail. Dude’s filthy rich (albeit with filthy teeth) and yet still living with his sister (who is far too enthusiastic about). Why not curb the Reconstruction-era Fight Club for a few and bag up a little lady to enjoy the white cake with? Instead, Calvin dies as he lived: surrounded only by sycophants.

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Fail Level: Simp Fatality

The classic cautionary tale for attempting to date out of your league. What do you get when you chase a chick for years, amass a fortune just to become a man she might deem worthy, and shower her with attention and spoils? Death. And on top of that, Daisy (Carey Mulligan) doesn't even actually leave her husband. As his filmography suggests, Leo was destined to play Jay.

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