On Sunday, the Academy Of Motion Picture Arts And Sciences will honor the best filmmakers working today. Only they won’t be recognizing all of the best filmmakers, because a very good and prominent actor was not nominated this year.
I refer, of course, to Mr. Leonardo DiCaprio.
I have an honest question: Have we as a society arrived at a moment in which we are taking Leo for granted? There he was, in Killers Of The Flower Moon, putting in work as an evil moron whose face is locked in permanent “goober” position. He was chilling, he was funny, he effortlessly held the screen, he fearlessly dared us to hate him. He was, as usual, fantastic. And yet his co-stars, Lily Gladstone and Robert De Niro, were (rightly) nominated for Oscars while Leo (scandalously) was overlooked. I feel like the world needs a reminder of who we are dealing with here. Therefore, I am going through Leo’s filmography, one movie at a time, and determining their chronological order based on quality.
Before we begin, I need to make a semantic clarification: I am judging these movies as movies, not necessarily as great Leo movies. However, there are movies that might be decent overall where Leo is amazing, just as there are movies that are better than decent overall where Leo is just okay. In these instances, I gave a slight edge to the “decent movie where Leo is amazing” movies. (This rule effects Gangs Of New York and This Boy’s Life the most, I won’t say which is which but you can probably guess.)
I know I have your curiosity, but do I have your attention? Good. This is the king of the world we’re talking about here. Let’s order up some fried sauerkraut!
PRE-LIST ENTERTAINMENT: AN ANTI-TRIBUTE TO “HEY LEONARDO (SHE LIKES ME FOR ME),” THE ’90S SONG THAT I (AND POSSIBLY LEONARDO DICAPRIO) HATE THE MOST
I loathe this simpering, whiny, pathetic little song. I hate how it sounds (like the bumper music for a forgotten sitcom that garnered high ratings because it followed Friends on Thursday nights one year) and I hate the lyrical conceit (this smug bugger doesn’t need a big screen TV or DVDs or the ability to sing like Pavarotti or the looks of a “hottie” to make his girl love him). I once almost burned down a CVS store because this POS song came on when I was looking for cough medicine. It sucks completely, thoroughly, overwhelmingly, and convincingly. And it blows with just as much power and conviction. This song sucks and blows like Andrew Dice Clay mowing down cigarettes in front of 18,000 idiots at Madison Square Garden in 1990.
Nevertheless: I am kind of obsessed with “Hey Leonardo.” I should say that I am obsessed with one particular aspect of “Hey Leonardo,” which is this: What does Leonardo DiCaprio think of “Hey Leonardo”? I have scoured decades of Leo interviews, and I couldn’t find one instance where he was asked this important question. Maybe nobody cares but me. That’s okay. I care enough for the entire world.
This song is not about Leonardo DiCaprio. Leo comes up exactly once, the same number of times as the fashion model Tyson Beckford and Fargo star Steve Buscemi. But the song is not called “Hey Tyson” or “Hey Steve,” even if those names are easier to sing. It’s called “Hey Leonardo” because the song came out in 1999, when Leo was still the nation’s reigning teen heartthrob. The reference skewers him as a signifier of the status that this simpering, whiny, pathetic little song feels insecure about. And it also exploits him as a magnet for attention, commercially and otherwise.
I assume Leo has heard this song. It peaked at only No. 33 in ’99, but I remember hearing it constantly. It was something that made you hope that Y2K wasn’t a hoax, as “Hey Leonardo” undermined the legitimacy of humankind’s survival. But what did Leo think? Did he find it cute or funny? I don’t know Leo at all, obviously, but based on his persona (serious, thoughtful, private) I’m going to guess he did not. Was he annoyed by it? Was this song a red flag signaling the possibility that he might potentially get stuck as an eternally 1990s caricature, like a method-actor version of Freddie Prinze Jr.? Did he think, I must work with Martin Scorsese so that people stop writing songs like this about me?
Did Blessid Union Of Souls actually help young Leo become the Leo we know today? Call me Leo. Let’s hash this out.
30. Don’t Look Up (2021)
In a 2005 Charlie Rose interview timed with the release of The Aviator, Leo reflects on his post-Titanic fame. “Hey Leonardo,” sadly, does not come up. What Leo talks about instead is earnestly using his platform for good, which for him means devoting himself to environmental causes. This is what compelled him to make three documentaries about global warming. This is a noble pursuit. (I have nothing else to say on the matter, which is why the docs won’t be mentioned again in this column.) I assume these principles also guided Leo toward Don’t Look Up. His intentions, no doubt, were good. This film, however, is not. It is the “Hey Leonardo” of Leonardo DiCaprio movies.
Leo’s most underrated attribute as an actor is his comic timing. When we reach the best movies on this list, we will find that Leo’s greatest performances are also his funniest. But while Leo can be pretty damn hilarious, it’s almost always in the context of serious films with weighty themes. When Leo allows himself to be funny, he’s usually not only funny. Don’t Look Up is the most straightforward comedy he has made. I wish Leo made more straightforward comedies. (I am guardedly optimistic that Paul Thomas Anderson will let Leo be funny in their upcoming collaboration.) Sadly, Leo is not funny at all in Don’t Look Up. Though, in his defense, if he had been funny it would have been jarring given that nothing in the film is funny.
29. Total Eclipse (1995)
I haven’t seen this movie, and I still put it at No. 29. That’s how much I despise Don’t Look Up. Virtually nobody has seen Total Eclipse. It grossed just over $340,o00 at the box office, and it’s all but impossible to track down now. I could have bought a used DVD copy for $80 on eBay, but that seemed a little steep for a film in which Leo plays the decadent French poet Arthur Rimbaud. This just feels very “Leo’s 29th best film” to me, sight unseen. If I find out that I’m wrong when I finally impulse-buy that DVD at 1 a.m. some random night, you have my apologies in advance.
Total Eclipse ultimately seems more crucial as a gesture than as a film. In various interviews, Leo has singled out the film (often without directly naming it) as an example of his father’s influence. George DiCaprio thought that playing Rimbaud would be an interesting choice, and Leo was guided by that suggestion. George later played a waterbed salesman in PTA’s Licorice Pizza, so the influence clearly goes both ways.
28. Critters 3 (1991)
In his Best Actor acceptance speech at the 2020 Screen Actors Guild awards, Joaquin Phoenix talked about being a young actor in Hollywood in the ’90s. He would go up for roles, he would get to the final callback, but in the end he always lost out to the same guy. A guy no other actor would name — out of reverence, and also out of envy. Even casting directors (in Joaquin’s retrospective telling) would only dare to whisper his name: Leonardo.
I’m guessing that Joaquin was talking about the mid-’90s. In the early ’90s, around the time he played a runaway on the ABC sitcom Growing Pains and before he broke through as a budding nü-De Niro in This Boy’s Life, Leo appeared in the crummy direct-to-video horror film that all actors are required to make early on. Though for Leo, his “crummy direct-to-video horror film” era was remarkably short. Within three years, he was nominated for his first Oscar.
27. The Great Gatsby (2013)
From practically the beginning of his career, Leo knew what kind of actor he wanted to be. He was serious. He was intense. He was self-punishing. Like Tom Cruise — whose preoccupation with working only with world-class, Mt. Rushmore-caliber filmmakers set Leo’s blueprint — his methodology was to put himself through hell and to let the audience know exactly how hellish this experience was. Over time, he also realized that playing creeps and losers and lowlifes effectively counterbalanced his movie star looks and charisma.
The Great Gatsby is the rare instance of Leo giving himself over fully to being a good-looking and charismatic leading man. He wears tuxedos and calls every man in his orbit “old sport.” It is all very, very boring. It becomes slightly less boring if you read The Great Gatsby as a meta-commentary on Leo’s dynamic with old friend Tobey Maguire, another peer who (like Joaquin) always seemed to lose roles to Leo back in their child-star days. Tobey became a star in his own right when he made the Spider-Man movies, though again Leo (who has made not making comic-book movies part of his brand) still comes out ahead on that count as well.
26. The Man In The Iron Mask (1998)
When people say “they don’t make movies like that anymore,” they usually mean the kinds of movies that Leonardo DiCaprio is still trying to make. Tough, ambitious, and expensive epics about important subjects that feature A-list talent in front and behind the camera. The great cinema reminiscent of the vaunted ’70s New Hollywood that all cinephiles valorize. The types of projects that only directors like Scorsese, Tarantino, Nolan, and PTA can still launch, sometimes with Leo’s assistance.
But “they don’t make movies like that anymore” could apply to other moribund genres and styles. Take the ’90s swashbuckling historical action film, an archetype defined by movies like Braveheart, the Kiefer Sutherland/Charlie Sheen version of The Three Musketeers, and this thoroughly forgettable movie that had the good fortune of arriving in theaters not long after Titanic. Nobody makes these kinds of movies anymore, and nobody is upset about that. The Man In The Iron Mask could have only come out in 1998, a carefree time when theatergoers paid good money to watch Gérard Depardieu fart on the big screen.
25. J. Edgar (2011)
Leo does not have a perfect batting average when it comes to making great movies. Nobody does. But his reasoning is always sound. There are no Madame Web-style, pure cash grabs in his filmography. On paper, you can understand that the potential for greatness was there. Yes, The Man In The Iron Mask isn’t very good, but it must have seemed classy on paper. Same with The Great Gatsby and Total Eclipse. And as much as I hate Don’t Look Up, the cast is incredible and the director once made Step Brothers. It didn’t work, but that doesn’t diminish Leo’s taste or wisdom. Leo, as always, tried.
For J. Edgar, he was working with Clint Eastwood. The subject matter was worthy and fascinating, and the screenplay thoughtfully considered J. Edgar Hoover’s possibly closeted queerness. On paper, it looked like a great film. On actual film, however, Leo is way too young to play Hoover, and the questionable make-up makes him look like a ham sandwich left out in the sun for 14 days.
24. Revolutionary Road (2008)
Still: Leo made a brave choice! It didn’t work, but you can’t hold it against him. His choice, again, was interesting, even if the movie itself wasn’t.
Here’s another interesting choice: Reunite with his romantic co-star from Titanic and spend the entire movie cheating on her and hurling chairs in her direction. As if that wasn’t perverse enough, he also signed up for love scenes with Kate Winslet as her husband, Sam Mendes, looked on as director. (Three years later Winslet and Mendes divorced, which we will insist on looking upon as a coincidence.) Revolutionary Road passes the “on paper” test. As for the “actual film” test, however, this is American Beauty set in the 1950s, with Mendes again laying on the heavy-handed treatment of alleged spiritual suffocation in the suburbs. (Only Win Butler has less respect for these environs.)
23. Blood Diamond (2006)
A film as generic as the title. Though Blood Diamond is notable for Leo having a slightly older leading lady, the implausibly luminous Jennifer Connelly, a phenomenon never repeated before or since. Weirdly, Leo landed an Oscar nomination for this movie even though The Departed came out the same year. (Apparently, Academy voters liked Leo’s Zimbabwean accent more than his Boston one.) The scene where Leo and Connelly flirt at the bar is easily the best thing in the entire movie, though Blood Diamond on the whole is pretty watchable despite being totally nondescript. I don’t know if I have ever willingly decided to watch Blood Diamond, but accidentally catching it after basketball games on TNT was always a non-tedious experience.
22. Marvin’s Room (1996)
An overlooked film from Leo’s 1.0 era, which is defined by our hero 1) playing troubled teenagers and 2) joining casts loaded with respected boomer-era stars. Leo was already famous in 1996, but he still wanted to pay his dues. Appearing in a middle-of-the-road family drama like Marvin’s Room was Leo’s version of doing an internship, in which he could shadow veterans such as Meryl Streep, Diane Keaton, and Robert De Niro. He plays Streep’s rebellious son, but many of his scenes are with Keaton, his cancer-stricken aunt. I’m not sure if this was intentional, but there is a weird sexual tension in their scenes together, with Keaton vibing hard on DiCaprio’s delicate, ’90s era pretty-boy features. Fortunately, she keeps the vibing in check, which safely places Marvin’s Room in a wholesome, non-illicit zone.
21. Celebrity (1998)
A very weird film. Leo uses Woody Allen (at a time when working with Woody Allen was a signifier of prestige and artistic authenticity) and Woody Allen uses Leo (to play an exaggerated version of the hot young movie star he was one year after Titanic). Leo is only in Celebrity for 10 minutes, and it’s simultaneously the most exciting and grating part of the movie. (Actually, Kenneth Branagh’s lead performance as Woody’s proxy is at least equally grating.) Looking back, it might be hard for modern audiences to understand why a guy like Leonardo DiCaprio would want to work with a writer-director who still used euphemisms like “lovemaking” in the late ’90s. But Leo’s performance in Celebrity can be viewed as a dry run for his gonzo work in The Wolf Of Wall Street — he snorts coke, he violently attacks his girlfriend, he initiates a four-way sexual tryst, even Donald Trump shows up (though not in the four-way). It’s all very proto-Jordan Belfort.
20. Don’s Plum (2001)
I watched this on YouTube as part of the preparation for this column. It’s not officially available anywhere. It might have been taken down from YouTube by now. (Don’t tell anyone I told you about this.) Leo and Tobey essentially blocked the release, and if you have seen Don’s Plum you understand why. Imagine your most embarrassing conversation from when you were 21 being filmed for the potential amusement of millions of strangers. (Also imagine that one of your conversation partners is E. from Entourage.) That’s what Don’s Plum is. It is a bunch of young L.A. actors improvising inside of a diner in the mid-’90s. They smoke a lot, they use a lot of homophobic slurs, they call each other “bro” 100,000 times, and they chew scenery like it’s sunflower seeds inside of a baseball dugout.
That said: I expected this movie to be way worse than it is. I actually enjoyed it. Perhaps I am biased because I smoked many cigarettes inside of diners in the mid-’90s. Don’s Plum made me nostalgic for my own dumb past. I also have a lifelong crush on Jenny Lewis, and hearing her talk dismissively about commercial grunge music makes me swoon. As for Leo, observers have long dismissed Don’s Plum as “Pussy Possé: The Movie.” However, I am praising this film as “Pussy Possé: The Movie.” While it was made at the height of 1.0 Leo, it was released at the end of the 1.0 era, when he aged out of his youthful enfant terrible phase and entered his conscientious “leading man” guise. Never again would we see Leo “bro down” like this again.
19. The Beach (2000)
Leonardo DiCaprio is like Radiohead — early in his career he seemed like a potential one-hit wonder, but he was able to move through different eras as he matured and, in the process, he endeared himself to multiple generations. He’s a ’90s band, but many fans believe he didn’t reach his full potential until the 21st century. (In this analogy, The Wolf Of Wall Street is Leo’s In Rainbows.)
But as is the case with Radiohead, Leo can’t ever fully shake his iconic ’90s status. Both Leo and Radiohead broke through to a rabid teen audience with possibly the most ’90s movie ever made, Baz Luhrmann’s Romeo + Juliet. (Shoutout to the “Talk Show Host” scene.) And then there’s The Beach, which technically came out in 2000 but nevertheless might very well be the second most ’90s movie ever made. This movie is so ’90s, Moby’s “Porcelain” makes an appearance. The movie is so ’90s, people lay on the beach and listen to Sugar Ray. This movie is so ’90s, the kids who threaten to spoil the movie’s titular utopian bubble do so while singing a Sublime song.
18. The Basketball Diaries (1995)
The fallout from The Beach was that Ewan McGregor (who was originally considered for Leo’s role) stopped being friends with director Danny Boyle for about 20 years over the perceived betrayal of being passed over for the hottest young male movie star in Hollywood. This, of course, was not Leo’s fault. Great directors wanted to work with him. Even when a more appropriate choice was standing right next to him.
We all know the most famous example. Paul Thomas Anderson sees The Basketball Diaries. He sees Leo, and he sees Mark Wahlberg. PTA decides he wants Leo for his next film, the L.A. porn industry epic that will make him a ’90s cinema legend. Leo is interested, but there is another epic on his horizon, the one about a boat as large as Dirk Diggler’s most famous appendage. PTA goes with Wahlberg instead. The rest is history.
Back to The Basketball Diaries. The movie is fine but the poster — the one with Leo in the prep school clothes looking longingly at the camera lens — was to teenaged girls in the ’90s what that Farrah Fawcett poster was to teenaged boys in the ’70s. The only thing better than the poster is the chemistry between Leo and Wahlberg. We all loved seeing Leo and Brad Pitt get together in Once Upon A Time … In Hollywood, but Leo’s on-screen partnership with Wahlberg is severely underrated. What makes it work is that they seem to sort of hate each other. And their sort of hatred is electric! (I also refer to their frenemy dynamic in The Departed.)
17. The Quick & The Dead (1995)
Let’s take a moment to ponder an intriguing sliding doors scenario: What if Leo played Dirk Diggler in Boogie Nights? Would it be a better or worse film? How does this affect Leo’s career moving forward?
I’ll take the first question last. As for the second question: I actually don’t think it would have affected Leo’s career that much one way or the other. If he doesn’t make Titanic, he is less famous. But Boogie Nights puts him in the position to make the kinds of films he wants to make regardless. He becomes the world’s handsomest character actor. He also installs himself in PTA’s repertory company of actors. Is it possible that he plays the Tom Cruise role in Magnolia? Does he take the Paul Dano part in There Will Be Blood? The mind reels.
Of course, this all hinges on the first question: Is Leo’s Boogie Nights any good? I think … so? I can see him killing both the pathos and the comedy the part requires. The Leo Boogie Nights totally works on paper. But we know all about Leo and “on paper,” don’t we?
Leo clearly made the right decision regarding Titanic. I am not about to question the man’s career savvy. He knew how to build a career slowly and methodically, and then explosively and massively. This included making another “internship” movie like The Quick & The Dead, in which he appears with the era’s biggest female movie star (Sharon Stone), an old-guard ’70s cinema legend (Gene Hackman), and another budding superstar who was decade older (Russell Crowe).
16. Body Of Lies (2008)
The world had to wait another 13 years for the next scintillating pairing of Leo and Russell Crowe. It finally came courtesy of another generically titled late aughts film (a la Blood Diamond) that is surprisingly watchable on basic cable. Like The Departed, Leo goes undercover to fight bad guys, only to find that his good intentions have been thwarted by a corrupt system. It’s a morality play with life-and-death stakes. A searing port- oh who am I kidding? This is Leo’s “dad movie” movie. I own it on Blu-Ray, though I don’t remember buying it. I assume the hospital sent it home with our first child.
15. Shutter Island (2010)
When I wrote my Martin Scorsese column, the loudest complaints came from the “Shutter Island stan” community. This community might not be large, but it is fervent. And, as I do with all manner of freaks and psychopaths, I respect these people. Shutter Island is bleak, and Shutter Island is depressing, and Shutter Island is a film I do not enjoy watching. But I understand that this is by design, and I admire the achievement. Steven Van Zandt once said that Bruce Springsteen’s only vice is “mentally beating the shit out of himself.” This is also true for Leo, and it is true for Marty. The emotional place where actor and director meet is their desire to self-flagellate. And Shutter Island is Leo and Marty in peak punishment mode— of themselves, of the audience, etc.
14. Gangs Of New York (2002)
The beginning of Leo 2.0. Like all transitional work, you can sense the awkwardness. Leo’s grasp of the Irish accent is as uncertain as a 2010s-era U2 album. You can feel him wanting to be a “tough adult male,” and it’s not as convincing as it needs to be. (This is another role that might have been better suited for Mark Wahlberg.) People forget this now, but coming out of the ’90s Leo had a reputation for being — to quote Senator John McCain, who for some reason felt moved to offer conservative commentary on young male actors — an “androgynous wimp.” Gangs Of New York is him operating in “I’ll show you” mode, and it doesn’t completely work.
Having said all of that … Daniel Day-Lewis absolutely rocks in this movie. He is the element that puts Gangs Of New York over the top. This is a good movie, but not a great Leo movie. That is why it is No. 14.
13. This Boy’s Life (1993)
The inverse of Gangs Of New York — a good movie overall, but a great Leo movie. Leo in This Boy’s Life has to be a Top 5 child-actor performance. Put him up there with Henry Thomas in E.T., Jodie Foster in Taxi Driver, Haley Joel Osment in The Sixth Sense, and Tatum O’Neal in Paper Moon. He exudes angst and pain. He hints at a well of emotion that is kept mostly under wraps. He does not laugh at Robert De Niro’s preposterous accent. It is truly excellent work.
12. Romeo + Juliet (1996)
The Revolver to Titanic‘s Sgt. Pepper in Leo’s filmography. I don’t necessarily mean that in terms of the respective movies’ quality. What I mean is that Romeo + Juliet set the table for Leo’s star-making Titanic moment. Baz Luhrmann shoots Leo like he’s a floppy-haired, chain-smoking angel sent from sexy guy heaven. He worships Leo like he’s Wayne Campbell meeting Alice Cooper for the first time. He sets up the movie in a manner that’s designed to make you forget all about James Dean in Rebel Without A Cause and John Travolta in Saturday Night Fever and Matt Dillion in Rumble Fish. Luhrmann wanted to transform what a generation of young straight women (and gay men and anyone else drawn to delicately beautiful dudes) wanted out of the masculine form. And he absolutely achieved it. Even now, nearly 30 years later, rewatching Romeo + Juliet makes Timothée Chalamet look like a bucket of dog biscuits.
11. What’s Eating Gilbert Grape (1994)
Of all the films on this list — even Don’t Look Up — this was the one I most dreaded revisiting. And I think the reason why is obvious: I wasn’t sure I wanted to see Leo do what he does here. Just like Walk Hard: The Dewey Cox Story made it difficult for biopics to run through the standard paces when depicting the lives of musicians, Tropic Thunder changed the game for actors looking to do, ahem, what Leo does in What’s Eating Gilbert Grape.
However, I was pleasantly surprised to find that What’s Eating Gilbert Grape holds all the way up. And that has a lot to do with Leo, who absolutely earned his first Oscar nomination for the work he put in here. In the long, shameful history of actors portraying cognitively disabled characters, Leo did it the best. (A partial list of those who did it the worst: Sean Penn in I Am Sam, Juliette Lewis in The Other Sister, and — this is dead last — Rosie O’Donnell in the 2005 TV movie Riding The Bus With My Sister.)
10. The Revenant (2015)
The Oscar movie. And, like Bradley Cooper before him, Leo was resented for this. The public could detect his thirst for the trophy throughout The Revenant. A man does not eat raw bison liver without expecting something great in return. We can see him trying very hard. We can see him trying, perhaps, too hard. If I’m being honest, “icicle-boogers hanging from an overgrown beard” Leo is not my favorite Leo. Nevertheless, this film is an achievement. Seeing it in a theater was an overwhelming experience. At home, the second-hand Terence Malick camera moves are less thrilling, but as I’ve previously stated I will never fault Leo for trying his hardest. If the Academy had simply honored him for The Wolf Of Wall Street two years prior this could have all been avoided.
9. Killers Of The Flower Moon (2023)
The least likable he has ever been on screen — at least his character in Django Unchained is awful and funny — which makes me admire Leo even more. Though it probably cost him the Oscar nomination. (That and his tireless campaigning for Lily Gladstone, who he put ahead of himself at every opportunity during Oscar campaign season.) Leo’s job in Killers Of The Flower Moon is to be simultaneously conniving and stupid, an impossible combination that Leo somehow lands while portraying the most detestable parts of both poles. He is sufficiently hatable while also being beneath contempt. Even his teeth are despicable. Of all his Scorsese collaborations, this is Leo giving himself over to the movie at the expense of his own juice on screen. It’s a great movie more than a great Leo movie, but that is wholly intentional.
8. Inception (2010)
Leo once again is a family man with a troubled wife. His perception of reality is skewed. Nothing is what it seems. He appears to be in control but he is actually deeply sad. It sounds like I am describing Shutter Island but I am actually talking about the more watchable Shutter Island. It’s less painful, and also less coherent (which is why it’s less painful).
7. The Aviator (2004)
The most underrated Leo movie. Based on the anecdotal evidence I have gathered from film conversations over the years, there’s an idea about The Aviator that it’s a little long, a little dull, and not worthy of slotting in Leo’s top tier. I disagree. It’s three hours, sure, but The Aviator moves like the Spruce Goose. And Leo has a lot to do with that. This was his first great performance as an adult actor, and it remains one of his most fully realized on-screen characterizations. He gets to be both the charming leading man and the character actor who shows us how effectively he can gradually lose his mind. When you see him pee into a jar, it feels authentic and glamorous.
6. Titanic (1997)
To circle back to my Radiohead analogy: If you grew up with Leo in the ’90s, this is his OK Computer, the big, fat emotional epic that seems a touch melodramatic to younger generations. But what do they know? If you were there, you were there. I was dragged to Titanic by my girlfriend at the time. Like many 20-year-old dudes in 1997, I dismissed Leo as the cinematic equivalent of a boy band. Deep down, I was surely jealous of his dominance of the collective American female libido. And then I saw Titanic, and I could not deny the man’s swag. Decades later, James Cameron claimed that Leo initially didn’t want to do the movie because there wasn’t anything for him to play. He couldn’t seize upon the theatrical tics that marked his performances in What’s Eating Gilbert Grape and The Basketball Diaries. Cameron replied that it’s actually harder to just hold the center of a movie as a steadying presence. He framed the role as a challenge, which was enough to trigger Leo’s self-punishment impulses. In the end, Cameron was right — Leo’s job was to be the dream boyfriend who drowns to death, and he stuck the landing.
5. Catch Me If You Can (2002)
Officially a Leo 2.0 movie, though it feels like Leo 1.0 because of his dynamic with Tom Hanks, the G-Man tasked with taking down Leo’s prolific con man while also leaning on his “America’s Dad” persona. It’s the last time where Leo plays a rebellious kid who just needs someone in authority to say “I love you.” It’s also the best job he did with that archetype.
4. The Departed (2006)
Just four years later, Leo again worked with an iconic actor from a different generation. Though with Jack Nicholson, he gets to be the relatively stable one while Jack plays with dildos and severed hands wrapped in plastic. The Departed also demonstrated that the Leo of Gangs Of New York had evolved into a more conventionally manly Leo capable of credibly portraying a Boston cop who does push-ups in prison while the Dropkick Murphys blast away on the soundtrack. The accent, again, wavers at times. But at no time do you doubt his character’s daily Dunkin consumption.
3. Django Unchained (2012)
The comedian Roy Wood Jr. has a great bit where he praises Leo for using so many N-words in this movie. If you’re going to accurately depict the historical arc of Black Americans on film, Wood reasons, you need white actors who are willing to do some truly heinous things. And Leo is about as heinous as heinous can be in Django Unchained. “That’s one of the bravest white allies I’ve ever seen in my life,” Wood says. “This dude went from Titanic to enslaver!” It’s a good joke and even better film criticism. I probably like The Departed slightly more than Django Unchained. But Leo’s gonzo performance as the loathsome Calvin Candie locks Django in the top three. Some actors can set aside their vanity, but Leo transcends his own moral vanity by playing one of the worst characters in modern cinema.
2. The Wolf Of Wall Street (2013)
I won’t tell you anything you don’t already know: Leo’s work here is a virtuoso masterpiece. There are so many scenes I could single out for praise. The Wolf Of Wall Street is like a greatest hits album of classic Leo scenes. The incredible act of physical comedy that is the quaaludes scene. The way he reacts to Kyle Chandler calling him “little man” on his yacht. His expert display of popping and locking. The “Steve Madden” speech. The McConaughey scene. All are incredible. But the scene I put above all the others is the “I’m not fucking leaving” speech. If you were to rank the greatest-ever line readings of Leo’s career, at least three would come from this scene. And No. 1 would have to be “I’MNOTFUCKIN’LEAVIN’!” (No. 2 is “The show goes on!” and No. 3 “Cuz I ain’t goin’ nowhere!!!”) I have watched this scene at least 50 times — half of those viewings were for this column — and it never fails to make me laugh. (And repulse me. And exhilarate me.)
1. Once Upon A Time … In Hollywood (2019)
It comes down to Jordan Belfort vs. Rick Dalton. The two best characters in the Leo-verse. It’s extremely close. If I wrote this column last week, I might have had a different verdict. But for now: I love Leo as Rick Dalton just a smidge more. As great as the “I’m not fucking leaving” speech is, I think the trailer meltdown from Hollywood is the single best scene of Leo’s career. In a career filled with emotional outbursts, this is his Mona Lisa — it’s hilarious and heartbreaking in equal doses. Really, all of the Lancer scenes are incredible, with Leo playing three-dimensional chess as he plays Rick playing Caleb DeCoteau. (Revisiting my line-reading list: Leo saying “Rick fucking Dalton” through tears is tied for No. 1.)
Like his work in The Aviator, this is Leo hitting both the all-time leading man and all-time character actor bases at the same time. Leo serves himself up as a self-pitying jackass, and he does it while looking cooler than he ever has on screen. I don’t think there is another actor right now who can come close to pulling off that magic trick. That is the Leo zone. That is why he’s one of the best.