The Great Gatsby
Carey Mulligan and Leonardo DiCaprio in "The Great Gatsby."

This weekend, “The Great Gatsby,” Baz Luhrmann’s overstuffed piñata of a literary adaptation, opens everywhere (read our review). Leonardo DiCaprio stars as the mysterious mogul Jay Gatsby, with Carey Mulligan as Daisy Buchanan, the object of his very intense desire. Anyone who has taken a freshman literature course (um, spoiler alert?) knows that the central love story of “The Great Gatsby” doesn’t exactly end well, but even more alarming is the fact that within the career of Mr. DiCaprio this seems to be what a therapist would describe as “a definite pattern.” Over the years Leo has been embroiled in a quite shocking array of cinematic trysts that ended in absolute catastrophe.

Through nightmares and dreamscapes, historical disasters and literary classics, DiCaprio has faced an almost unrivaled myriad of doomed romances. He finds love -- fleetingly -- only to have it ripped away from him, usually in the most depressingly tragic way possible. "The Great Gatsby" is no exception. It is at least his first doomed romance in 3D, so there's that. Without further ado -- the top 5 Leonardo DiCaprio doomed romances!

"Revolutionary Road"
Paramount Vantage "Revolutionary Road"
"Revolutionary Road" (Sam Mendes, 2008)
The Romance: Frank (DiCaprio) and April (Kate Winslet) are a married couple in suburban Connecticut in the '50s. He commutes into the city while she stays at home with the kids. They once deeply loved each other, and spoke about leaving their dull life behind and moving to Paris. Sadly, that never gets to happen.
How It's Doomed: Frank and April's relationship is wracked by conflict – screaming matches, infidelity, and general unease – but the tragic end to their marriage occurs after April becomes pregnant. She tells Frank that she wants to get an abortion, which sends him flying into a rage. Later on, she tries to give herself an abortion… and things do not end well. Under the direction of Sam Mendes, "Revolutionary Road" unfolds as a series of mournful tableaus and the final abortion sequence is jaw-dropping precisely because it's so well composed. In the history of Leonardo DiCaprio wives who crazily kill themselves, though, Winslet has a surprising amount of depth – her decision doesn't seem all that nutty, partially because Mendes is such an empathetic director.
Emotional Devastation Factor: Pretty high. This was, after all, the highly touted reunion of DiCaprio and Winslet, who co-starred in the sweepingly romantic (and equally doomed) "Titanic." That was, at one point, the biggest movie of all time. "Revolutionary Road," by comparison, was small potatoes, but it might have packed an even bigger emotional wallop.

Leo Shutter Island

"Shutter Island" (Martin Scorsese, 2010)
The Romance: Teddy Daniels (DiCaprio), a U.S. Marshal, is investigating a missing mental patient named Rachel Solando, a resident of the insane asylum on Shutter Island, a craggy mass in the Boston Harbor. Solando apparently drowned her children – but why is Teddy wracked with similar visions?
How It's Doomed: "Shutter Island" unfolds with a loopy, nightmarish logic all its own but what's eventually revealed is this – Teddy isn't actually a U.S. Marshal but is in fact a patient – a man who killed his wife after she drowned their children. The entire plot of "Shutter Island" it seems, is an elaborate attempt to uncover repressed memories and free DiCaprio's character (whose name is really Andrew Laeddis) of his insanity. DiCaprio doomed romances don't usually have this much murder and mayhem (expertly visualized by Scorsese, who is clearly having the time of his life referencing dozens of B-movie chillers).
Emotional Devastation Factor: Surprisingly low. There's just so much stuff in "Shutter Island" (including but not limited to: Nazi doctors, World War II flashbacks, multiple actors playing the same characters, and hazy fantasy sequences) that it's hard to make an emotional connection to any of it. Still, Scorsese tries his best, and the scenes where we see what really happened with DiCaprio's wife and children, are pretty disturbing, even if they are still ensconced in Scorsese's cobwebby haunted-house aura.