I’m not finished talking about Leonardo DiCaprio quite yet. The Oscars awoke my Leo obsession. Suddenly I’m a teenager again and everything is Leo ❤️ ❤️
A few weeks ago I re-watched Romeo & Juliet. It had been a few years and I forgot how amazing yet utterly ridiculous the film is. The main thing I noticed this time around was how Romeo and Jack Dawson are essentially the same character. Which really shouldn’t have been a surprise as they’re both characters in tragic forbidden love stories. But then this got me thinking – Leo’s early career was dominated by these romantic heartthrob roles and while this hasn’t really continued throughout his career, I realized that Leonardo DiCaprio characters don’t have a history of getting the girl and having that happily ever after ending.
Warning: Below are spoilers for basically every Leo movie ever made!
Let’s look at the evidence:
Romeo & Juliet – Romeo and Juliet see each other across the fish tank and it’s love at first sight. After a whirlwind romance and quick marriage things go downhill pretty quickly. This is one occasion where not one, but both romantic leads meet their untimely end. No happy ending for anyone.
Titanic – Jack sees Rose at a distance and it’s love at first sight. After a secret love affair aboard a doomed ocean liner Jack ultimately sacrifices himself to save Rose. Rose goes on and lives happily for another 80 years but there’s no happy ending for Leo. I’m still sobbing over this one.
Catch Me If You Can – Amid Frank’s various schemes he falls for young and naive Brenda. He fills her head with lies and then, after actually admitting the truth to her, he hatches a plan for the two of them to elope. Unfortunately she isn’t a fan of the crimes and sets him up. Yet again, he doesn’t get the girl.
The Aviator – In this film Howard Hughes has both Katherine Hepburn and Ava Gardner at some point, as well as a string of young starlets. However, he looses them all. His paranoia, depression and ultimate mental breakdown didn’t bode well for any of these romantic entanglements. This one his character brought on all by himself.
The Departed – The love story in this Best Picture isn’t very prominent, however, Billy has a secret affair with Madolyn, his boss’s girlfriend, who ends up pregnant. But of course, things don’t end well and Billy dies (along with a number of other characters). Leo doesn’t survive this one, which is something we hadn’t seen in a few years.
Revolutionary Road – Oh Revolutionary Road, that time he lost Kate Winslet a second time. This movie starts well – he is happily married to the girl – but it all goes downhill from there. It becomes a troubled marriage and the main characters start sleeping around. Finally, after a botched abortion attempt April Wheeler dies in the hospital. Leo let her slip through his arms again, though this time it’s she who doesn’t make it.
Inception – Things get complicated here. Cobb and Mal spend fifty years in a dream world constructed of their shared memories. When Mal refuses to return to reality Cobb does some complicated things to wake her up. After doing so things take a turn for the worse when she refuses to believe the actual world is real and commits suicide in an attempt to “wake up” from the dream state. It’s messy, but so is Inception. But all that really matters here is Leo doesn’t end up with the girl.
The Great Gatsby – Oh Gatsby, such a tragic character. Gatsby has loved Daisy for years and has been pursuing the American Dream and working to establish himself as worthy ever since he met Daisy when they were young. Unfortunately, Daisy has moved on while Gatsby is stuck in the past. No matter what he does he will never be able to win her back. This tumultuous tale ends with Gatsby facedown in a pool, without the girl.
The Wolf of Wall Street – Here Jordan Belfort does get the girl. For awhile he has a hot, young wife and even a child. However, this ultimately ends in divorce because of his numerous bad habits and cocaine addiction. No happy ending here.
There’s also the numerous films where there isn’t much of a love story for Leo’s characters, including Django Unchained, Blood Diamond, What’s Eating Gilbert Grape, J. Edgar, Shutter Island, Man in the Iron Mask and The Revenant.
There is one exception to this. In Gangs of New York Leo just might get the girl and that happy ending. After an abundance of riots and gang fights Amsterdam and Jenny leave New York City and its turmoil behind (at least according to the wikipedia article… I admit it’s been years since I saw this movie).
There you have it. The characters Leonardo DiCaprio has chosen just don’t have the best romantic luck. Here’s hoping this changes moving forward… or at least in his personal life perhaps he’ll finally get and keep the girl. I’m all for finally getting that happy ending with Kate Winslet ❤️ ❤️ .
Till next time,
– Justine Alyssa