10:41 pm - 05/09/2013

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?'

"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.

"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?

Other two movies are at the source!
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crucified 10th-May-2013 02:55 am (UTC)
The music that plays during that scene in the gif for Shutter Island is so beautiful.
eveofrevolution 11th-May-2013 02:52 am (UTC)
lbr all the music for Shutter Island is fantastic. So haunting, it's unreal.
notoriousreign 10th-May-2013 02:56 am (UTC)
Omg Shutter Island was depressing.
possevi 10th-May-2013 02:56 am (UTC)
Other two movies on the list are Inception and Titanic. ;)
chuk_is_dazzled 10th-May-2013 03:03 am (UTC)
thank you, so not about to click that source lmao
scriptedending 10th-May-2013 02:57 am (UTC)
I liked Revolutionary Road, but R+J still hits me harder. He was so hot... and so angsty. I cry 50% of the time that I watch it.
sarahvma 10th-May-2013 02:57 am (UTC)
Obligatory "God Leo was so beautiful when he was young" comment.
takeurtime 10th-May-2013 03:03 am (UTC)
Sometimes he still is pretty good looking but he will forever be such a pretty young person ha.
nicolesnitchie 10th-May-2013 03:07 am (UTC)
ugh he wasn't even really attractive when he was young.
eaglefan2011 10th-May-2013 03:10 am (UTC)
i like him more now
lovepollution 10th-May-2013 03:13 am (UTC)
My 12-year-old self with my bedroom covered in Leo posters very much disagrees.
lovelyeli 10th-May-2013 03:28 am (UTC)
he was attractive in that baby face kind of way..but to me he looked hotter in his late 20s early 30s tbh
squirrelsarerad 10th-May-2013 03:09 am (UTC)
hes still beautiful imo
agentnever 10th-May-2013 03:18 am (UTC)
Seriously. I feel like he'd only be appealing to teenagers when he was young because he was such a pretty boy. Now that I'm older, I think he looks good older.
toldmelies 10th-May-2013 03:20 am (UTC)
I always say this and my dad gets so upset - "What do you mean? He's so handsome now!"
greenfairy_87 10th-May-2013 03:22 am (UTC)
I'd still hit it. He looks amazing in Gatsby, it's just some actor's faces really puff out once they reach 40.
ace_nikkei 10th-May-2013 05:59 am (UTC)
ain't that the fucking truth.
emmy0001 10th-May-2013 03:00 am (UTC)
I think Revolutionary Road could be his best performance. There is something so chilling about it.
little_vienna 10th-May-2013 03:03 am (UTC)
IA. I think it's because the story and characters are more grounded and relatable (and almost more realistic, really) than many of his other films. It's not a crazy dream world or Shakespeare in the 90s--it's about a guy and a girl trapped in the life that society expects them to do and they're snapping under the strain and pressure of it all.
saikaro_x 10th-May-2013 03:22 am (UTC)
love your icon. i've probably told you this before but i can't remember lol.
jearsforqueers 10th-May-2013 03:16 am (UTC)

algore_galore 10th-May-2013 03:29 am (UTC)
lovelyeli 10th-May-2013 03:29 am (UTC)
because it felt so real..like i know i was bawling my eyes out during those argument scenes because they reminded me of my parents :/

kate&leo r too good for this world ugh.
marielaurie 10th-May-2013 04:43 am (UTC)
ia, the hospital scene is just heartbreaking.
wizard_alien 10th-May-2013 05:33 am (UTC)
Sounds wonderful and depressing, I need to see this.
ace_nikkei 10th-May-2013 06:01 am (UTC)
i absolutely agree.
pinkjaffa 10th-May-2013 12:55 pm (UTC)
I've been meaning to watch Revolutionary Road for years, but since I know what happens, I'll have to be in the right mood. It's the same with The Reader for me- I own that one, but I know I'll be so depressed afterwards.
16_bit_goddess 10th-May-2013 02:31 pm (UTC)
that movie was devastating...amazing writing + acting
hangthemj 10th-May-2013 03:01 am (UTC)
shutter island was fucking awesome imho
arya14 10th-May-2013 03:08 am (UTC)
One of my favorites. Love it!
foureyedgirl 10th-May-2013 03:17 am (UTC)
ita. it was amazing
saikaro_x 10th-May-2013 03:22 am (UTC)
i loved it
wizard_alien 10th-May-2013 05:36 am (UTC)
I love it too, even though I guessed he was crazy halfway through.
masterofmystery 10th-May-2013 03:01 am (UTC)
so right about half his filmography? hell, even j edgar had a doomed relationship lmao
viciouslush 10th-May-2013 03:01 am (UTC)
Has Leo ever starred in a movie where he actually had a happy romantic ending? I can't think of any.

Also I hated Shutter Island. Everything about that movie sounded awesome and everything about it was actually terrible.
pussy_posse 10th-May-2013 03:04 am (UTC)
Gangs of New York
Catch Me If You Can if you factor in the real person's ending lmao
nicolesnitchie 10th-May-2013 03:07 am (UTC)
yeah, it was kind of boring. i thought it was going to be way better.
warsawed 10th-May-2013 03:45 am (UTC)
Shutter Island made me feel so cheated. I've never felt more like I wasted time watching a movie than I did with that one.
heart_iswild 10th-May-2013 05:31 am (UTC)
omg never watch the movie Take Shelter. talk about a waste of time
milly 10th-May-2013 04:29 pm (UTC)
I felt cheated too, but mostly because I had guessed the ending from the trailer, and watched basically thinking that it was too obvious an ending, so it had to be something different. But nope.
eaglefan2011 10th-May-2013 03:02 am (UTC)
love him and most of his movies
devetu 10th-May-2013 03:02 am (UTC)
so excited for the great gatsby

takeurtime 10th-May-2013 03:03 am (UTC)
I haven't seen Revolutionary Road yet but I am thinking I should.
masterofmystery 10th-May-2013 03:05 am (UTC)
brace yourself, that shit was intensely depressing
missdisco 10th-May-2013 11:03 am (UTC)
and for like 20 minutes of shouting and arguing.

I found that the most frustrating part. All the shouting.
alethaweapon 10th-May-2013 03:10 am (UTC)
ugh . It should just be called 'So This Is Divorce'.
jearsforqueers 10th-May-2013 03:15 am (UTC)
it's soooo depressing but at the same time it was so good.

imo, i think kate and leo were perfect in that film and both deserved awards for it.
saikaro_x 10th-May-2013 03:23 am (UTC)
great performances but really depressing.
greenfairy_87 10th-May-2013 03:24 am (UTC)
Take every stereotypical image of cheerful people enjoying the convenience of the 50's then shoot them in the face repeatedly.
routinesummer 10th-May-2013 04:59 am (UTC)
do it! hands down, my favorite leo movie.
chuk_is_dazzled 10th-May-2013 03:04 am (UTC)
shutter island is so sad. i watched it on a school night at like midnight and it kinda messed me up for the day
kellybsblover 10th-May-2013 03:04 am (UTC)
Probably my favorite scene in a movie:
alethaweapon 10th-May-2013 03:09 am (UTC)
mte. I thought it would be this cheesy teen version but holy shit- Baz Luhrmann knows what he's doing.
doimoveyou 10th-May-2013 03:34 am (UTC)
squishinator 10th-May-2013 03:16 am (UTC)
young leo was so cuuuuute
summerstar882 10th-May-2013 03:21 am (UTC)
The scene brings back my 90's adolescent feels like nothing else.
greenfairy_87 10th-May-2013 03:26 am (UTC)
As soon as I saw this scene done in Panty and Stocking I knew the anime I was watching had reached greatness territory.

thespockingdead 10th-May-2013 03:52 am (UTC)
This scene. This movie. Ugh, I love it all so much.
My ~*Shakespeare Snob~*~~ friend thinks she sounds so intellectual calling it trash, but idgaf. These stories were fucking made to be interpreted in different ways, and Baz's version affected me way more than the other ones I've seen. It's perfect.
liddles15 10th-May-2013 04:16 am (UTC)
Re-watched this last week and cried during this scene. Baz captured love at first sight perfectly.
deathbytamarind 10th-May-2013 05:18 am (UTC)
I love this movie without shame.
ace_nikkei 10th-May-2013 06:08 am (UTC)
ugh, my feels. i love this fucking movie.
16_bit_goddess 10th-May-2013 02:33 pm (UTC)
god, I really need to see this.
erised_mirror 10th-May-2013 03:58 pm (UTC)
I love this movie, I love this scene, AND I LOVE THIS SONG.
barilace 10th-May-2013 03:05 am (UTC)
All of us plebs must bow down to Leo's exquisite man bro pain. :')
masterofmystery 10th-May-2013 03:08 am (UTC)
he should actually avoid that role, it's never gotten him an oscar nod (the aviator is debatable)
barilace 10th-May-2013 03:12 am (UTC)
I don't actually think he cares as much as people think he does. He just wants to do his ~~~true art~~~ which he sees as playing someone who is ~complex~ and ~emotionally and psychologically in pain~. I would put money on him continuing to do these same types of roles yeaars after he actually wins an Oscar.
duckyduck92 10th-May-2013 03:39 am (UTC)
I don't understand how it is debatable that the aviator got him an oscar nod, because it did.
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