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

From Romeo to Gatsby, things have a habit of going poorly for this leading man.

Not Available Lead
Complex Original

Image via Complex Original

Not Available Lead

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)

Arthur Rimbauld and Paul Verlaine in Total Eclipse (1995)

Not Available Interstitial

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).

[via]

Romeo + Juliet (1996)

Not Available Interstitial

Jack Dawson and Rose DeWitt in Titanic (1997)

Not Available Interstitial

King Louis XIV and Christine in The Man in the Iron Mask (1998)

Not Available Interstitial

Brandon Darrow and Unnamed Girlfriend in Celebrity (1998)

Not Available Interstitial

Richard, Sal, and Francoise in The Beach (2000)

Not Available Interstitial

Frank Abagnale Jr. and Brenda Strong in Catch Me If You Can (2002)

Not Available Interstitial

Howard Hughes and Ava Gardner in The Aviator (2004)

Not Available Interstitial

Billy Costigan Jr. and Dr. Madolyn Madden in The Departed (2006)

Not Available Interstitial

Frank and April Wheeler in Revolutionary Road (2008)

Not Available Interstitial

Andrew Laeddis and Dolores Chanal in Shutter Island (2010)

Not Available Interstitial

Dom Cobb and Mal in Inception (2010)

Not Available Interstitial

J. Edgar Hoover and Clyde Tolson in J. Edgar (2011)

Not Available Interstitial

Calvin Candie in Django Unchained (2012)

Not Available Interstitial

Jay Gatsby and Daisy Buchanan in The Great Gatsby (2013)

Not Available Interstitial

Latest in Pop Culture