The Top 5 Leonardo DiCaprio Movies About Doomed Romances

The Top 5 Leonardo DiCaprio Movies About Doomed Romances

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(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.

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.

Inception” (Christopher Nolan, 2010)
The Romance: Dom (DiCaprio) and Mal (Marion Cotillard) are so happy together that they actually create an entire universe in their dreams. When they unplug, though, the relationship (and their sense of reality) comes crashing down.
How It’s Doomed: Mal, unable to handle the effects of leaving the dream world and convinced that reality is also a construct, hurls herself off the side of a building (on date night, no less). What’s worse is that a version of Mal, more villainous than in real life, haunts Mal as he makes his way through the dreamscape (since her death, he has become a renegade dream thief), foiling him at every turn. She really is the ex that you can’t get away from. While director Christopher Nolan has a history of creating female characters who are morally reprehensible or end up violently killed, Mal is more than that – she works on a metaphorical level as well as a literal one, and adds some devilish kinkiness to a movie that, even though it involves the psychologically murky world of dreams, is starkly asexual.
Emotional Devastation Factor: Middle. It works on a surprising emotional level, especially considering that “Inception” was the second Leo-trapped-in-dreams movie of 2010 (after “Shutter Island”). Cotillard’s performance, especially in her “human” scenes, is particularly affecting – she seems like the kind of woman that would make you create a fantasy dimension just so you could have her all to yourself. Leo is also solid, playing a man chasing this memories of a better life through his dreams. As Robert Palmer would say: “Tell me I’m not dreamin'”

Romeo + Juliet” (Baz Luhrmann, 1996)
The Romance: Star-crossed lovers Romeo (DiCaprio) and Juliet (Claire Danes) have one of the most crushingly powerful and tragic romances of all time, defying a violent grudge between their families.
How It’s Doomed: Based on William Shakespeare‘s immortal play and transposed to what appears to be war-torn, modern-day South America (with flourishes borrowed from Southern California and, of course, Australia), Romeo and Juliet’s love affair ends with both of them taking their lives. (It’s a little convoluted – read the play.) This was Luhrmann’s first collaboration with DiCaprio, on probably the only source material that is more sacred than “The Great Gatsby,” and the two are obviously on similar creative ground. The tragedy is heightened by the fact that both DiCaprio and Danes are both so young and adorable. It’s like drowning fluffy kittens.
Emotional Devastation Factor: High. This is one of the most gut-wrenching love stories of all time, and Luhrmann and his actors do it justice, especially since, by the time the tragic final scenes play out, much of the showy excess has been stripped away. What’s left is two kids, dead by their own hands, and really, what’s more heartbreaking than that? 

Titanic” (James Cameron, 1997)
The Romance: It’s an upstairs/downstairs romance on the RMS Titanic as dirt-poor Jack (DiCaprio) falls in love with Rose (Kate Winslet). They have to dodge Kate’s hothead fiancé (Billy Zane) as well as dealing with the whole ocean-liner-sinking-into-the-depthless-sea thing.
How It’s Doomed: Considering the movie is bookended by a sequence of an old lady telling her story to a group of modern day Titanic enthusiasts (led by Bill Paxton‘s redneck researcher), it’s safe to say that only one half of this relationship survives the cataclysmic crash of the Titanic. Of course, they make it through the actual sinking of the ship to find themselves floating in the chilly Atlantic waters, waiting for rescue. Rose is perched atop a piece of wood, while Jack dangles underneath. Eventually, he dies, his half-frozen body sinking into the water. Cue the wailing cries of millions of teenage girls worldwide. DiCaprio’s tragic demise is even more harrowing considering how much the couple got through on the boat alone (including Billy Zane firing a pistol at them, and the ship cracking in half as it began its slow descent to the bottom of the ocean) – if they can conquer all that, as well as the rigid class system of the time, shouldn’t they be able to hang out in the water for a few minutes before getting rescued? No. This is a DiCaprio romance. Somebody had to die.
Emotional Devastation Factor: Again: pretty high. James Cameron is a master manipulator, able to wring tears out of virtually any situation, and man if you don’t get drawn into the story of these two kids in love, then you’re probably a robot. The emotions are actually amplified by the historical setting, unlike “Pearl Harbor,” which tried a similar formula but felt much cheaper. Coming a year after “Romeo + Juliet” too, “Titanic” served as a would-be warning to any cinematic partner interested in a relationship with DiCaprio: things most likely won’t end well.

While not quite as histrionic, a number of other Leonardo DiCaprio romances have also felt doomed: his relationship with Armie Hammer in Clint Eastwood‘s “J. Edgar” never had a big moment of dissolution but was tragic for its quiet lack of acceptability; in Steven Spielberg‘s “Catch Me If You Can,” he has a wonderful relationship with Amy Adams that is undone by his criminal duplicity; he forges a meaningful relationship with Vera Farmiga in “The Departed” but is ultimately killed (insert sad emoticon here); and his own mental instability means that he can never sustain a romantic relationship in “The Aviator.” Poor Leo!

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Leonardo DiCaprio is one of the best actor in Hollywood in my personal opinion. He is the style icon and source of inspiration for me, i love his each movie outfits and purchased some of those to get his elegant looks!
Great Gatsby White Suit


A couple of typos and errors here and there nearly take you out of the story, but an interesting piece nonetheless. This fits into DiCaprio's shtick of playing Byronic heroes pretty well.


Leo seems to be on a major slide. There's a hilarious huffpost story up mocking all the screaming he's done in movies.

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