Over the last 20 years, Leonardo DiCaprio has churned out more memorable performances than most actors do in a lifetime.  He has become, in my humble opinion, one of the greatest actors of our generation.  And in celebration of his 40th birthday, I dug through the archives and came up with a list of his nine best movie moments. Yes, I said nine, I’m rebelling.  I’ll leave the tenth one up to the readers, so leave a comment below with your pick. Now let’s get started.

9. Romeo + Juliet (20th, Century Fox, 1996)

Romeo Juliet

Leo emerged as a major heartthrob in the late 90’s, and thanks to his run as Romeo himself in most tragic love stories of all time, teens around the world were actually willing to read their Shakespeare.  Or at least, they watched the movie and thought they did a good job at pretending they read their Shakespeare.  Either way, we all would have taken poison for him any day of the week.  Even when Leo’s spouting off Shakespeare he still manages to bring the emotion, as he does here during a show down between Romeo and Juliet’s cousin Tybalt.

8. Titanic (Paramount Pictures, 1997)


One year after Romeo + Juliet, Leo cemented his status as most coveted boyfriend alive when he portrayed Jack Dawson the epic romantic adventure Titanic.  Although this film is full of memorable (and steamy) moments between Jack and Rose, it’s that famous scene with that one line you all have shouted at least 20 times over the last two decades (don’t lie, you’ve done it too).  It’s a snapshot of this character’s free spirit and contagious carefree outlook, which is a side of Leo we don’t get nearly enough of.

7. Inception (Warner Bros. Pictures, 2010)


Before you all yell at me for putting Inception so low on this list, let me just clarify that it’s one of my favorite movies of all time.  But one of the best things about this movie is that it’s so solidly cast, with each performance balancing the other, creating very few standout moments for a particular character.  That being said, Cobb and Mal’s relationship adds a layer of emotional depth to this otherwise strictly cerebral science fiction film, and they share some stunningly genuine moments.  Cobb’s reaction as Mal jumps to her death is shocking and raw and one of the best of these moments.

6. The Aviator (Warner Bros. Pictures 2004)


A Leonardo DiCaprio and Martin Scorsese team up, the result is never disappointing, and The Aviator is no exception, raking in eleven Oscar nominations and winning five.  The film follows the life of Howard Hughes as he grew his wealth and battled his obsessive compulsive disorder.  Leo was given a Best Actor nom for his role as Hughes, and the scene where he loses control while demanding a set of blueprints shows him at his best as he attempts to maintain control over himself speech.

5. Wolf of Wall Street (Paramount Pictures, 2013)

Wolf of Wall Street

Leo’s performance earned him an Oscar nomination last year (can someone please tell me why this guy hasn’t won one yet?) with his balls to the wall, disturbingly unhinged portrayal of Jordan Belfort in the controversial film The Wolf of Wall Street.  This one has plenty of his signature freak out moments to choose from, but one hilarious depiction of a serious drug trip stands out as such an uncomfortable, outrageous moment for the him.  Although a tremendous actor, Leo doesn’t have more than a handful of comedic moments in his career, so we have to treasure them.

4. What’s Eating Gilbert Grape (Paramount Pictures, 1993)

What's Eating Gilbert Grape

DiCaprio kicked off his silver screen career with a bang, earning his first Oscar nomination for Best Supporting Actor in one of his earliest films as Arnie Grape.  Although the film’s focus is primarily on Johnny Depp’s character (Gilbert Grape) and the hardships of supporting his family and caring for his brother, DiCaprio steals scene after scene in his shockingly  honest performance as Arnie, particularly in the scene where he doesn’t understand why he can’t wake his mother.

3. The Departed (Warner Bros., Paramount Pictures, 2006)

The Departed

The Oscar winning crime drama, The Departed, features yet another team up of Scorsese and DiCaprio.  This time around Leo plays an undercover cop (Billy Costigan) who’s tasked to infiltrate the crew led by Irish mob boss Frank Costello.  This cast is full of heavy hitters, and although the always larger than life presence that is Jack Nicholson is a scene stealer as he’s able to showcase that unhinged side of his, Leo grabs his moments.  And one of the best of these moments is when he confronts Matt Damon’s character on a rooftop as he leads him down an elevator to what turns out to be his own departure.

2. Django Unchained (The Weinstein Company, 2012)

Django Unchained

Two very special things happen during Quentin Tarantino’s controversial Western film: 1) Leonard0 DiCaprio plays a villain, which is a rare and delightful thing to watch. And 2) Leo slices his hand open during a take and proceeds to roll with the punches, working his cut hand into the scene as he continues with his speech, wiping his own blood on Kerry Washington’s face (I’d say that shock on her face wasn’t an act).  Now that’s called improvising.

1. The Basketball Diaries (New Line Cinema, 1995)

Basketball Diaries

Is The Basketball Diaries Leonardo DiCaprio’s best film?  No, not even close.  Does this movie showcase the best full performance of his career? Debatable, but probably not.  But he gives us one of the most disturbingly raw and uncomfortable moments I’ve ever seen in his portrayal of Jim Carroll, a high school basketball star who falls victim to a heroin addiction.  While suffering through withdrawals, Jim approaches his mother for money.  What follows after is a heartbreaking exchange between a mother and her son, who she has to punish in order to help.  This moment is a showcase of the talent DiCaprio will continue to tap into over the next 20 years and more.