An Ode to Leo: Looking Back on Mr. DiCaprio’s Best Roles Yet

I remember sitting in the theater as the credits rolled on opening night of Martin Scorsese’s Shutter Island. As Max Richter’s "On the Nature of Daylight" played softly, my best friend and I sat in silence, quietly weeping to ourselves. And although the film was a wonderfully-shot journey of psychological thrill, it was Leonardo DiCaprio’s performance that moved us to tears. Did we have our own flair for the dramatic? Yes. But really, he was just so good we couldn’t help but succumb to our emphatic emotions.

But it’s always that way—no matter the film, in the twenty years that he’s been gracing our screens, Leo has never given a bad performance. Whether he’s playing a mentally-handicapped teenager coping with the strains of family, an infamous imposter conning his way around the world, a family man wrestling with the trials of love, or a psychopathic slave-owner, he always delivers a performance that’s brimming with conviction, intensity, charm, and agility—with that signature essence of Leo that lingers even when he disappears into his characters.

And this week, we’ll see him take on one of his most anticipated roles yet as the iconic role of Jay Gatsby in Baz Luhrmann’s lavish reimagining of F. Scott Fitzgerlad’s The Great Gatsby. So in honor of, what I am sure is to be another brilliant performance, here’s a look at some of Leo’s best roles throughout the years. And for good measure, a few old interviews with the young star before he went on to be Hollywood’s most beloved leading man. Enjoy.


The Aviator as Howard Hughes, 2004

What’s Eating Gilbert Grape as Arnie Grape, 1994 


DiCaprio, 1995


The Departed as Billy, 2007


DiCaprio, 1995


Gangs of New York as Amsterdam Vallon, 2002

Romeo + Juliet as Romeo, 1997


Django Unchained as Calvin Candie,  2013


DiCaprio, 1997


Marvin’s Room as Hank, 1996

Revolutionary Road as Frank Wheeler,  2009


Catch Me If You Can as Frank Abagnale Jr., 2003 

Behind the Scenes Rome + Juliet

Titanic as Jack Dawson, 1998 

Shutter Island as Teddy Daniels, 2010

The Basketball Diaries as Jim Carroll, 1995

Ten Movies You Shouldn’t Watch Alone on Valentine’s Day

Back when I was single, I didn’t put too much stock in Valentine’s Day. (I still don’t, really; I’ll probably stay in and watch movies with my boo.) But I also never really did it right, either. One year, I came home from work, opened a bottle of red wine, and watched the 1977 film version of Equus, which had just arrived from Netflix. You know, there’s nothing like a lighthearted movie about a naked teenager murdering horses! It’s quite charming. Another year, after my boyfriend dumped me three days before Valentine’s Day in a Chipotle, I stayed in with a friend (who had recently broken off her engagement) and watched The Departed. Not too cheery!

So please, don’t make the same mistakes I have made. Here are some movies you should probably avoid watching at home alone this Valentine’s Day.

Sophie’s Choice

You’d think surviving the Holocaust would be bad enough, but then Meryl Streep’s Sophie comes to America and things don’t really work out so well for her.

Kramer vs. Kramer

Meryl Streep is in a lot of sad movies, although this one does have a precocious child actor in it. Don’t let that fool you!


Do you like genital mutilation? Then sure, go on, watch the movie that perfectly portrays Lars von Trier’s slow decent into madness.

Eternal Sunshine of the Spotless Mind

It’s romantic, sure, but even though it has a somewhat happy ending, Eternal Sunshine is not the kind of thing you’ll want to watch tonight.

Paris, Texas

First of all, you really have to give yourself a lot of time to get through this one. It’s long and slow. It’s gorgeous, though, but definitely not a feel-good flick.

The Ice Storm

This is the opposite of any movie that made the ’70s look groovy and fun. The clothes are claustrophobic, the mood is tense, and key parties, for the record, are very emotionally complicated!

Celeste and Jesse Forever

Don’t let the familiar funny people in the lead roles fool you: this movie is bleak.

Far From Heaven

Things sucked for women and gay guys even more back in the ’50s, basically.

Half Nelson

There’s nothing romantic about this one, unless you consider the love for a crack pipe to be heartwarming.

Requiem for a Dream

Sure, it’s a lively little romp through the perils of addiction, but you might have a nightmare that your Valentine is a rabid fridge monster who wants to eat you.

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