Jordan Ruimy ranks his favorite DiCaprio performances

With the release of “The Revenant” just a few months away we caught a sneak peek of its trailer last week and, suffice to say, we were thrilled to see the potential on display. The impact this movie could have on awards season is HUGE and we couldn’t be more psyched to get a look at this bad boy in the near future. The biggest question headed towards the film’s release is whether or not this could finally be Leo’s big moment to win the golden statuette, a statuette that’s eluded him since his first nomination more than 22 years ago. Of course, awards don’t mean much in the grand scheme of things, if one were to make a list of cinematic greats that have failed to ever get the award it would be an endless, horribly frustrating list to look at.

DiCaprio’s been nominated four times in his career. Never has he really had a shot with any of those nominations. Most people would just shun him off by saying the nomination was enough, but was it? Along with Joaquin Phoenix we are seeing the emergence of an iconic American actor, one who never plays it safe and always goes for the risky, adventurous fare. Just take a look at the list of filmmakers this 41-year-old actor has worked with: Scorsese, Spielberg, Inarritu, Nolan, Tarantino, Allen, Cameron, Eastwood, Scott, Mendes. A who’s who of great directors. He sure knows how to pick ‘em and yet I get the feeling he’s only getting started and is going to keep pushing the boundaries further in the years to come. Here are ten times DiCaprio proved he was one of the very best actors of his generation.

1) Jordan Belfort, “The Wolf Of Wall Street”

This was the best shot our boy’s had thus far — key words being “thus far”. The sky’s the limit for DiCaprio, and in Scorsese’s now classic epic of debauchery, he brought a whole new range to his repertoire. With some scenes veering towards slapstick comedy, Leo’s portrayal of a Wall Street madman could have quite easily tipped over the top towards caricature, but I don’t think anyone could have pulled it off better than he did. It was a very divisive movie upon its release, but has gained notoriety over the last few years and will continue to do so as a classic. It is the riskiest performance DiCaprio has given us and quite possibly the beginning of an artistic freedom that will have him venture into even more unknown territory, like, for example, Inarritu’s “The Revenant”.

Nominated? Yes.
Who won? Matthew Mcconaughey, “Dallas Buyers Club”

2) Howard Hughes, “The Aviator”

Martin Scorsese’s movie is the best ever made about OCD. A mental disease that hasn’t really been understood or treated in the best of ways in pop culture. DiCaprio beautifully captured Howard Hughes’ inner and outer demons in a lavish but personal movie. There are some moments with the tiniest of details that it’s very easy to miss them. Hughes was a neurotic, eccentric billionaire who, as his obsessive compulsion grew, isolated himself entirely from society. This could have been the one to win it all for the then 30-year-old actor. A big budget Hollywood epic, that dealt with an industry legend. Every note was perfect in the performance, capturing the quirks and eccentricities that come with having the mental disorder.

Nominated? Yes.
Who won? Jamie Foxx, “Ray”. DiCaprio won the Golden Globe.

3) Arnie Grape, “What’s Eating Gilbert Grape?”

Tropic Thunder’s Kirk Lazarus said you should never go “full retard.” Crude phrasing aside, DiCaprio clearly didn’t get the memo. It’s in Lasse Hallstrom’s touching film that I first noticed a then 19-year-old actor stealing scenes from Johnny Depp. Playing a character with a developmental disability is not the easiest task to tackle for a young actor, let alone a veteran actor. I didn’t know DiCaprio back then and actually believed that a mentally challenged actor was playing Arnie Grape — that’s how great this performance was. Not many people knew who DiCaprio was, but after watching this movie you sure as hell weren’t going to make that same mistake again. Here was a performance that captured all the details, big and small, and made them feel so real.

Nominated? Yes.
Who won? Tommy Lee Jones, “The Fugitive”

4) Billy Costigan, “The Departed”

When you’re in the same movie as an over-the-top but equally brilliant Jack Nicholson, or have to share screen time with a swear-a-minute ticking time bomb cop played by Mark Whalberg, good luck getting the recognition you deserve. That’s what happened here. DiCaprio’s was the most subtle of performances: a calm, cool and collected guy having to deal with the anarchy unfolding in a society about to breakdown and trapped in unique circumstances where he can’t tell the good guys from the bad guys. Scorsese’s best movie since “Casino” or even “Goodfellas” had DiCaprio in his most emotionally and physically complex role carrying the movie through its twists and turns.

Nominated? No. At least the Globes nominated him.
Who won? Forest Whitaker, “The Last King of Scotland”

5) Jack Dawson, “Titanic”

Can any true movie fan really deny the fact that DiCaprio got robbed of a nomination for this movie? Kate Winslet and Gloria Stuart got nominated. It was in fact DiCaprio who carried the movie on his then lanky shoulders, giving it soul and putting a heartbeat to the corny dialogue James Cameron is so well known to write for his films. This is also the movie that many people claim will be the reason why DiCaprio will never win the big award. Leo-Mania was huge. He was a heartthrob who stole millions of hearts, but so what? Ironically enough Jack Nicholson won that same year for playing an OCD-ridden Grinch in “As Good As It Gets”. But if you want a truer depiction of OCD go check out “The Aviator”.

Nominated? No. At least the Globes Nominated him.
Who won? Jack Nicholson, “As Good As it Gets”

6) Calvin Candie, “Django Unchained”

Christoph Waltz won the big prize for “Django”, and he was great, but you know who was equally great? Dicaprio as Calvin Candie: A looney, absurd, frightening performance this otherwise mess of a movie needed. Yes, the performance was over the top, but that’s the kind of thing that was required to get to the eccentric tone of the character just right. A professional connoisseur of the Mandingo game, Candie might just be the most despicable person in the entire movie, a bigoted fool who has enough money to build his own nightmarish empire-esque version of Neverland, this one aptly titled “Candieland”. Not even a nomination for this brilliant portrayal of absurd proportions. At least the Globes nominated Leo alongside Waltz.

Nominated? No.
Who Won? Christoph Waltz, “Django Unchained”.

7) Teddy Daniels, “Shutter island”

Here’s a film that got no Awards love whatsoever. Relegated to a February release back in 2010, Martin Scorsese’s expertly tense horror movie has, rightfully so, had its reputation grow in stature over the last few years. Every decade there are films that were ill-received upon their release and then get reassessed later on and are proclaimed great movies. The scantily underwhelming 68% RT score and 63 on Metacritic that “Shutter Island” got are quite shocking considering that its IMDB rating now is at 8.1 with almost 700,000 votes. “Shutter Island” can now be considered one of the very best releases of 2010, with DiCaprio giving an exquisitely layered but brutally honest performance as Teddy Daniels, a man trying to relocate himself and his disturbed past. No Awards love but, something better, a reputation that far exceeds any awards, that of a classic.

Nominated? No.
Who Won? Colin Firth, “The King’s Speech”.

8) Frank Abagnale Jr, “Catch Me If You Can”

What a playful, enjoyably persistent performance by DiCaprio. Steven Spielberg took Leo’s charisma and infectious personality and used it to move his film into such cheery, infectious territory. This was only five years after “Titanic”. DiCaprio had just come out of relative failures such as “The Man in the Iron Mask”, “Celebrity”, and “The Beach”. With all three movies he was trying to destroy his public image as the pretty boy next door. What he didn’t realize was that he could use his aforementioned image and charisma to give us this great performance. Abagnale Jr’s escapades are so absurd yet they all actually happened. The real life Frank had such a great personality that he got away with almost every bad deed he did. DiCaprio shone because he did just that; he used his attractiveness to mold a character that we cheered for, even as he was breaking the law and making the FBI look like idiots. What is there not to like? Looking back on this performance we can see just how tough a performance like this can be, yet DiCaprio made it look effortless.

Nominated? No.
Who Won? Adrien Brody, “The Pianist”.

9) Danny Archer, “Blood Diamond”

This performance he actually got nominated for. In this case, nomination was probably enough. Justified in fact, but nothing more, nothing less. “Blood Diamond” has a classical narrative that wholly suited this kind of performance. It’s sorta like when Marlon Brando got nominated for “Viva Zapata!” — great acting, but you knew there was so much this actor could do if it were a better screenplay. The role of Danny Archer wasn’t really written with any real subtleties or foreshadowed characterizations, but he was played by DiCaprio with such movie star vigor that it ended up getting him a nomination. That’s no small feat. The film has been reasonably better received over the years, with an 8.0 rating on IMDB, and it’s one of the last movies where the highly talented Jennifer Connelly would get a decent script to work with. Sad.

Nominated? Yes.
Who Won? Forest Whitaker, “The Last King of Scotland”.

10) Cobb, “Inception”

Cobb has to be included. Of course this was “The Christopher Nolan Show,” but without Leo’s central performance it wouldn’t have been as good. Nolan’s words can sometimes be very cold and distant, but Leo brought real humanity to the screenplay and a beating heart to his character that another actor might not otherwise have achieved. No small feat. In fact, imagine “Inception” without DiCaprio … you can’t. I view Nolan — exception to the rule being “The Dark Knight” and Heath Ledger’s cuckoo brilliant performance — like the puppeteer of the whole enterprise, just having his way with the actors as they basically recite the words he’s written down for them. He’s like the hypnotist just manipulating his actors into doing whatever the hell he wants them to do, without giving them any room or freedom. This is not necessarily a bad thing considering some of the great movies he’s given us, but this makes DiCaprio’s performance all the more accomplished, since he was able to give us a pretty great performance out of the restrictions at hand.

Nominated? No.
Who Won? Colin Firth, “The King’s Speech”.