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)