Leonardo DiCaprio Turns 39 today! From 'Titanic' to 'Gatsby' see Leo Through The Ages

Oh Leo, let us count the ways in which you have melted our hearts. You first slayed us as the adorable and optimistic Arnie Grape in 1993's What's Eating Gilbert Grape. Then you progressed into heartthrob status when you took on Shakespeare's most icon male in Romeo + Juliet. And don't even get us started on how we, too, would like to be painted like "one of your french ladies" in Titanic.

To celebrate 39 years of Leo, take a look back at some of his most memorable roles.

What's Eating Gilbert Grape

In 1993, audiences were introduced to a talented and unknown actor named after an acclaimed artist/ninja turtle. Leonardo DiCaprio played Arnie Grape, a mentally challenged child who knew a secret: His brother was the greatest human to ever live. And in the greatest pairing in cinematic history, Johnny Depp portrayed the big brother to DiCaprio and the world collectively swooned.

Image: Paramount

The Quick and the Dead

I caught a few minutes of this movie on TV the other day, and it's definitely one of the worst Westerns made in recent history. That being said, the 1995 flick does feature a pubescent Leo who totes a gun, wears a cowboy hat, and attempts to make a move on a woman twice his age. You go, Leo!

Image: TriStar

The Basketball Diaries

You remember The Basketball Diaries, even if you never saw the 1995 bball movie, you certainly remember the VHS cover. No? Let me refresh your memory: Teenage Leo leaning up against a wall, wearing a school boy-esque suit and tie, disheveled hair and a mean, angry (yet smoldering) expression that says, "I'm so angsty and angry at life, come closer, I dare you!" Challenge accepted.

Image: New Line Cinema

Romeo + Juliet

Oh Romeo, Romeo! Wherefore art though, Romeo?

We know where he is, he's having pool make-out sessions with pre-cry face Claire Danes and fueling all of our teenage fantasies with open, billowing shirts.

Image: Twentieth Century Fox


Rarely do I hold grudges against films for as long as I've pined over the ending of Titanic. Yes, Leo dies, and that is sad and everything, but what is worse is the fact that he indisputably could have lived. Leave it to Mythbusters to prove just how Jack Dawson could have survived the tragic sinking of the Titanic, and continued to paint portraits of Rose in the style of "French ladies" until the end of time. F*ck you, James Cameron.

Image: Twentieth Century Fox

The Man in the Iron Mask

What would The Parent Trap look like if it starred Leonardo DiCaprio? Look no further than The Man in the Iron Mask.

Image: United Artists Corporation

The Beach

The Beach is Blue Lagoon meets Lord of the Flies, but half as amazing as that actually sounds. It does, however, include a tropical sex scene with a young Leo DiCaprio and a not that young Tilda Swinton, and who doesn't want to watch that awkwardness unfold on screen?

Image: Figment Films

Catch Me if You Can

Having finally come into his full heartthrob potential, Leo stars in the 2002 adaptation of the true story of Frank Abagnale Jr., who took on the faux roles of doctor, pilot, and legal prosecutor to con his way into millions of dollars worth of checks. As much as we realize how illegal and terrible it is that Leo is conning — and sleeping — his way into millions, we continue to root for him to get away with it because really, how impressive is that? And how good does Leo look in that captain's hat?

Image: DreamWorks SKG

The Aviator

Airplanes. Money. A bout of craziness. Peeing in jars. These are the things I recall about 2004's The Aviator. The film also won a shit ton of Oscars — including best picture, best actress, and a best actor award for Leo — so it's probably worth seeing, despite the jars of urine.

Image: Miramax

Blood Diamond

2006's Blood Diamond is about three men fighting over a precious gem and the war that surrounds the bloody business of diamonds. In case you haven't yet seen the political drama, we won't give anything away, except to say things don't necessarily end well for Jack Daw—I mean, Leo.

Image: Warner Bros.

Shutter Island

Shutter Island is one of those mind-bending thrillers that completely turns whatever you thought you knew on its head, aka the best kinds of movies. Leo plays a federal marshal in the 1950s who has been tasked with the job of finding a murderess who escaped from a hospital for the criminally insane. And in the end, Leo actually turns out to be the escaped murderess. Just kidding...or am I?

Image: Paramount


When Christopher Nolan directs a film starring Leonardo DiCaprio and (then newcomer) Tom Hardy, only good things can happen. That is, if you consider losing your wife and children "good".

Image: Warner Bros.

The Great Gatsby

Let's be honest, there is really no other actor who could have pulled off playing Jay Gatsby better than Leo. And it didn't hurt that in his final moments in the film he's adorned in little more than a body-clinging swimsuit. You have our attention, old sport.

Image: Warner Bros.

The Wolf of Wallstreet

I can say without an ounce of doubt that the trailer for The Wolf of Wall Street, in theatres Dec. 25, is by far the greatest trailer produced this year. Not only does it deliver the best application of Kanye West's "Black Skinhead," but it showcases Leo and Matthew McConaughey creating sounds with their mouths that should really earn them both Oscar nods. Or at least be made into GIFs.

Image: Red Granite Pictures