Career Best: Leonardo DiCaprio

I’m in 8th grade, and I’m sneaking into a movie for the first time. It’s sold out, so we bought a ticket to a different movie, probably some crappy comedy marketed to my teenage brethren, and we’re sneaking into the one we actually came to see. There are still a couple seats up front that we immediately grab, and we lean back and crane our necks to take the biopic in. Howard Hughes towers over us, flying Katharine Hepburn over the city, admiring his massive jumbo jet, repeating “Show me the blueprints” over and over, peeing into milk bottles. The actor playing him redefines acting for me at a time when I still have dreams of acting for a living, of making art and telling stories for the rest of my life.

Leonardo DiCaprio has been my favorite actor since I saw him that night in The Aviator. He’s the best actor and movie star of his generation, and I’m convinced it’s not close. He built his career from the ground up, from child star to ingénue to movie star to movie mogul. Having secured his wealth and bankability early in his career, DiCaprio has the luxury to pick and choose his roles, prioritizing auteur directors over box office potential, so he’s had the most consistent filmography of any 21st-century star. Partnering with Alejandro Iñárritu for the upcoming The Revenant continues that trend.

Leo is also a fascinating persona outside of the movies. The allure he holds as a man of wealth and a playboy and a philanthropist is akin to pre-Amal George Clooney or a real-life Tony Stark. Because he’s never settled down and he expresses such deep emotion in his movie roles, I always wonder if he feels fully satisfied, if he ever wonders if there’s more to this world than the instant gratification of his riches or the tortured pathos of his art. Maybe someday in the future we’ll gain insight into his psyche, but for now, in the 25th year of Our Leo, we can at least look back at his career so far. Here’s a ranking of all of his movie performances, from the not good to the perfect.

(Disclaimer: The clips in the title links may contain profanity. Actually, they probably all do.)



Celebrity (1998), Brandon Darrow (audio is out of sync)
Critters 3 (1991), Josh
Don’s Plum (2001), Derek
Poison Ivy (1992), Guy
Total Eclipse (1995), Arthur Rimbaud
The Wolf of Wall Street (2013), Jordan Belfort

These are all the Leo movies I haven’t seen, The Wolf of Wall Street the only one by choice. Well, I suppose I chose not to see the other ones too, but the rest of them wouldn’t have been free. I couldn’t track them down at the library or on Netflix, and I didn’t care enough to look for them illegally or to buy them on Amazon. None of them have a good reputation, or even any reputation at all- except The Wolf of Wall Street, of course, which I’m choosing not to see because of its reputation for end-to-end sexual content. It’s a shame, because I’ve heard it’s among Leo’s best performances. But it doesn’t seem worth it.


Not good

21. J. Edgar (2011), J. Edgar Hoover

This is DiCaprio’s only bad performance. It’s hard to blame him for it though. Clint Eastwood’s movie is such a mess across the board, and it’s not DiCaprio’s fault the age makeup is terrible. He’s a good enough actor that he can play old and it’s not weird, but everything about his performance as the old Hoover is made weird by fatsuits and bad bald wigs. Nothing works, not even Leo. But it’s the only movie of his you can say that about, which is better than almost anyone else can say.


Not not good

20. The Basketball Diaries (1995), Jim Carroll
19. This Boy’s Life (1993), Toby
18. The Quick and the Dead (1995), Kid
17. The Man in the Iron Mask (1998), King Louis XIV / Philippe

As a boy from 1993-2000, DiCaprio exhibited two traits better than any others: idealism and petulance. Unfortunately, these roles are all petulant kids, which makes them less likeable than his others from this period. The Quick and the Dead’s Kid is at least as endearing as he is arrogant, so he’s at least fun to watch, even if he’s a caricature of an archetype, like almost every other character in the Tarantino-scripted movie. And in The Man in the Iron Mask DiCaprio actually plays two characters, only one of whom is petulant; the other one is in a metal mask for most of the movie, so he hardly counts. And while his performances in The Basketball Diaries and This Boy’s Life are probably accurate depictions of male adolescence, his characters’ entitlement really grates the nerves. As his career progressed, his characters’ flaws wouldn’t decrease, but they certainly became less annoying.


You had my curiosity, but now you have my attention.

16. The Beach (2000), Richard
15. Marvin’s Room (1996), Hank
14. Romeo + Juliet (1996), Romeo

It’s not that DiCaprio was so much older in these movies than in the previous four, but the performances are all much more mature. Surely part of the reason is that these three are just better movies with better direction, so he had stronger guidance. The Beach is the strangest movie of the first half of his career, but because it’s the latest his performance seems much more assured than most of what came before. If it weren’t for the movie’s strange turn in the last quarter, which includes a bizarre acting decision from Leo, The Beach would be higher on this list. Marvin’s Room has DiCaprio as a character much like his roles in The Basketball Diaries and This Boy’s Life, a willful and rebellious teenager, but Scott McPherson’s screenplay gives Leo more room to show his joyous side, making it the most rounded of the three performances. And Romeo + Juliet, far and away the best film mentioned so far with Baz Luhrmann’s now signature flourishes, is Leo at his most enamored, a Leo entranced by his Juliet’s beauty, even more so than Jack in Titanic. These three movies give you a glimpse of both the level of skill he’d display in the 2000s and the kinds of adult characters he’d be most suited to.

T.I.A. This Is Acting.

13. Gangs of New York (2002), Amsterdam Vallon
12. Body of Lies (2008), Roger Ferris
11. Blood Diamond (2006), Danny Archer

Ah, here we go. This is the Leo we’re most used to now, the Leo who takes roles that require Acting and makes it look like he’s only acting. DiCaprio had struck gold before 2002 (see below), but Gangs of New York began a stretch of projects that he took on very particularly, choosing carefully which directors to whom he would give his time (and sometimes money as a producer). Gangs is also the first of his so far five-movie oeuvre with Martin Scorsese, and, while it’s the worst, it might be the biggest challenge, considering he was pitted against the titan Daniel Day-Lewis and a miscast Cameron Diaz. He acquits himself well though, taking that petulance so prevalent in his early movies and applying it to a noble character to turn that negative quality into honor. Body of Lies and Blood Diamond have DiCaprio playing essentially the same character, with his role in Blood Diamond a little more nuanced. Both movies have Leo as an opportunistic ass trying to make do in a volatile foreign situation. However, Blood Diamond has DiCaprio pulling off an effective South African accent, so it has the slight edge.


O trespass sweetly urged! Give me my sin again.

10. Revolutionary Road (2008), Frank Wheeler
9. Shutter Island (2010), Teddy Daniels

We love to watch DiCaprio suffer, apparently. He keeps taking painful roles, and we keep watching him. The Revenant won’t be any different, if the buzz from its production is to be believed. In Revolutionary Road he’s suffering from a failed marriage to Kate Winslet’s April. Some people don’t like RR, because it’s just Winslet and DiCaprio fighting for two hours. But I think it’s incredible, because despite all the yelling and selfishness from the two main characters, both have a hope that they’ll find happiness. They’re just unable to articulate it. In Shutter Island, Leo’s suffering from past trauma brought on by his wife’s murder of their three children. Shutter Island was fascinating the first time, but Leo’s performance is even more entrancing the second time through, because his desperation takes on new meaning after you know the twist ending.


I’m the king of the world!

8. What’s Eating Gilbert Grape (1993), Arnie Grape
7. Titanic (1997), Jack Dawson
6. Catch Me If You Can (2002), Frank Abagnale Jr.

These are some of DiCaprio’s most fun roles to watch. If the last two were painful to watch (on purpose), these three are a joy. Arnie in What’s Eating Gilbert Grape is one of Leo’s first film roles, which blows my mind, since Arnie is intellectually disabled and DiCaprio basically goes “full retard”, a big risk for even a mature actor and generally a terrible idea. But DiCaprio and director Lasse Hallström make Arnie’s main trait his infectious happiness, so if Leo got any of the physical characteristics of Arnie’s disability wrong, you’d never notice, because you’re too busy falling in love with the kid. Jack Dawson is a romantic idealist, but he’s also worldly, so we trust him implicitly from the beginning of Titanic. And Frank Abagnale in Catch Me If You Can is a charming narcissist, whose narcissism manifests in entertaining con jobs that make up the bulk of Spielberg’s movie, so Leo is entertaining from beginning to end. We tend to reward actors for suffering in their roles, but sometimes the harder job is making the audience love your character. DiCaprio pulls it off wonderfully in these three films.


Is it possible? Is it possible to improve on perfection?

5. Inception (2010), Cobb

I didn’t see Inception’s Cobb on a lot of the Top 10 Performances for Leo around the Internet. It seems underrated to me, probably because Christopher Nolan movies don’t showcase performances like other directors’. It’s unfortunate, because this is the performance in which DiCaprio does the most expressing with the least effort. Cobb is a man on a mission, and his determination is clear, even when marred by guilt over his wife’s deterioration. The final moment of the movie, when he stares one last time at the spinning top and then tears himself away from his totem to join his kids, is one of my favorite DiCaprio moments.


4. The Great Gatsby (2013), Jay Gatsby

Leonardo DiCaprio is Jay Gatsby. Gatsby is such a classic literary character that he should have been impossible to bring to the screen. But DiCaprio lives a Jay Gatsby life, with models at parties on yachts, in Cannes and L.A. and the Caribbean, spending more money in a week than I’ll make my whole life, wealthy beyond anyone else’s wildest dreams. The extravagance of Leo’s performance matches the exuberance of Baz Luhrmann’s direction. There’s also a hint of Gatsby’s green light on DiCaprio’s real-life persona; surely all his exploits with his riches have exposed a little emptiness in his heart? Jay Gatsby is Leonardo DiCaprio.


3. The Aviator (2004), Howard Hughes

This is the first moment we knew Leonardo DiCaprio could fulfill the promise he had shown in his twenties. Howard Hughes, much like Gatsby, was a larger-than-life man, and the mythos of Leo’s celebrity lifestyle hadn’t solidified in the public consciousness quite yet when The Aviator came out. But DiCaprio fills Hughes’ pilot boots and more, from his charm to his OCD tics, from his ambition to his resignation. It’s not that he wasn’t a good actor before The Aviator, but we weren’t sure if he would ever be truly great. The Aviator is his announcement that he skipped great and went straight to timeless.

2. The Departed (2006), Billy

Now they’re just toying with us. DiCaprio’s and Scorsese’s third partnership is their best and most complex, with DiCaprio as an undercover cop in a Boston organized crime family. Leo isn’t required to do a lot of extraneous acting in The Departed. The movie around him is so well-constructed and his character so well-written, his performance doesn’t have to carry the movie, even if it is the best performance in the movie. The whole thing, from his performance to the rest of the cast’s to the story execution itself, feels so effortless, you’re surprised at the end when Billy’s death hits you in the gut, and you realize you’re sad you don’t get to watch DiCaprio battle the demons of undercover life anymore.


1. Django Unchained (2012), Calvin Candie

Funny that the best performance by such a big movie star would be one of his few supporting performances. Calvin Candie may be a smaller role than the rest of DiCaprio’s filmography, but the performance is just as big. While Leo has played many bad people before, the only other villain he’s portrayed was in The Man in the Iron Mask, and King Louis is a saint compared to Candie. It’s not that Candie is that much scarier or more violent than other slaveowners in movie history; Michael Fassbender’s Epps from 12 Years a Slave would scare Candie out of his well-shined shoes. But what makes Candie different from a bastard like Epps is that he’s under any delusions that he’s anything more than evil. He’s a fitting reflection of the society around him in that he’s perfectly willing to treat Django like a white man but willingly- no, happily- pits his slaves against others’ to the death. And yet DiCaprio is an absolute pleasure to watch; he’s completely depraved, but his charm is off the charts. He steals the movie right out from under the capable noses of Jamie Foxx and Christoph Waltz, even if Waltz is the only one who ended up with an Oscar. The movie’s delicate balance of outrage and farce doesn’t work without DiCaprio.

In fact, after 25 years, one could argue that the movies don’t work without him.


3 thoughts on “Career Best: Leonardo DiCaprio

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