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This article was originally published in 2015 and has been updated to include the actor’s latest comedic works, including this weekend’s About My Father.

Robert De Niro famously will appear in just about anything you’ll pay him to, and nowhere is this clearer than in his comedies. De Niro ostensibly gets comedic mileage from “sending up” his cinematic persona, but the problem is that he keeps doing it over and over. He has made more than 20 comedies, and almost all of them hark back to earlier, far more well-thought-out roles. After a while, you’re not doing a self-aware parody; you’re just doing a lazy riff that wrings whatever little comedy there is out of an audience’s existing preconceptions.

De Niro is certainly capable of being funny: He’s not just a great actor who sometimes does funny movies, but actually a master of crack comedic timing who’s awfully good at the well paced double-take or delicious slow-burn. It’s just that his comedies so rarely ask very much of him. He’s usually just there to mug, or to “be De Niro.”

Still, there are some gems in there if you know where to find them. Thus, a definitive, sometimes-depressing ranking of De Niro’s comedic roles. A note on methodology: We didn’t include Silver Linings Playbook and Jackie Brown, two movies that aren’t considered comedies even though they obviously have big laughs. We understand if you feel differently; we were a bit torn on it ourselves.

24. Dirty Grandpa (2016)

There is depressing, there is dispiriting and then there is Dirty Grandpa. Where do we start with this one? Maybe the scene where De Niro, as the titular Dirty Grandpa, masturbates while watching an amateur porn film starring two octogenarians? Yeah, actually: That seems like a pretty reasonable place to start. The “gimmick” of this road comedy is that De Niro’s Dick Kelly — yes, the movie does have jokes about his first name! — loses his wife and requests his grandson (Zac Efron) to drive him to Daytona Beach, mostly so he can take a bunch of drugs and try to be co-eds. That’s pretty much the whole film, though that tidy plot summary does ignore the time De Niro sticks his penis in a sleeping Efron’s face. (All told, Efron looks less embarrassed than De Niro does.) The movie inexplicably features Aubrey Plaza and Zoey Deutch as two sexpot coeds, who, fortunately for them, are not involved in the scene featuring De Niro rapping “It Was a Good Day” and being cheered for using the n-word. This movie should be executed in the public square.

23. Little Fockers (2010)

The three Fockers movies made $1.2 billion worldwide and are easily the most lucrative project with which De Niro has ever been involved. Pretty impressive, considering the two sequels are nearly unwatchable. Little Fockers, the third installment, finds Greg (Ben Stiller) and Pam (Teri Polo) inviting their folks to their home, which gives Greg another opportunity to spar mirthlessly with Pam’s former–CIA agent father, Jack (De Niro). Ten years earlier, Meet the Parents succeeded because Stiller’s nebbishy panic worked so well off De Niro’s tight-lipped stare-down. But by Little Fockers, neither actor looked especially excited to still be a part of the franchise, and it comes through in De Niro’s listless performance. When people lament what’s become of the two-time Oscar winner, this is one of the movies that’s often cited.

22. The Big Wedding (2013)

There’s little quite so dispiriting as a talented cast that can’t even muster up the energy to even go through the motions. De Niro plays the father of the bride who has to pretend he’s still married to his ex-wife (Diane Keaton) to placate the Catholic parents of the groom. The high jinks that ensue are labored, to say the least; the whole cast — including Susan Sarandon, Katherine Heigl, Robin Williams, and Amanda Seyfried — appear to say their lines with one eye on their next project, something they’re undoubtedly more excited about. De Niro seems to be running out of air halfway through his lines; he looks like he refused to do any second takes. We don’t blame him.

21. Meet the Fockers (2004)

Meet the Parents was such a big hit that it made sense that Universal would want to do a follow-up. But Meet the Fockers is definitive proof that comedy sequels are a terrible idea: What was unexpected and charming the first time around quickly curdles when you try to replicate it. In the second film, we meet Greg’s parents, a tortuously eccentric Dustin Hoffman and Barbra Streisand, and the overacting infects the entire cast. De Niro was superb in Parents, but here he’s pure ham, turning Jack Byrnes into a gruff dolt as the humor gets crude and slapstick-y. Not that audiences cared: Fockers made almost $280 million, becoming 2004’s fourth-biggest hit.

20. New Year’s Eve (2011)

Somehow even worse than Valentine’s Day, director Garry Marshall’s previous foray into holiday-themed cinematic drudgery, New Year’s Eve cuts between several different New York City subplots as characters you can’t stand figure out how to spend their evening. It’s some consolation, then, that De Niro maintains his dignity, playing a dying man in a hospital who wants to see the ball drop one last time. This means he gets the “serious” story line amid the froth, and the actor wisely doesn’t overdo the waterworks, bringing a little gravitas to what is, essentially, the film’s “live life to the fullest” subplot. Does this mean De Niro fanatics should seek New Year’s Eve out? Oh, good heavens, no. Still, New Year’s Eve does provide us the answer to the unasked question, “What’s the only movie to star Robert De Niro, Ashton Kutcher, Lea Michele, Seth Meyers, and Jon Bon Jovi?”

19. Showtime (2002)

This was released right in the wake of the De Niro comedy boom — three years after Analyze This and two years after Meet the Parents — when Hollywood seemed to think De Niro was just a comedy dynamo ready to be paired with a wacky partner and countless spit-takes. (We really were only a couple years away from De Niro and his incorrigible but lovable police dog.) Here, De Niro and Eddie Murphy come together at low points in each other’s careers; Murphy would release this, Nutty Professor II: The Klumps, Dr. Doolittle 2, I Spy, and The Adventures of Pluto Nash in a two-year stretch — what a run! This is the sort of movie that thinks it’s hilarious to have William Shatner play a TV director who, after De Niro (playing a real cop paired with a “motormouth” cop for a reality-TV show) botches a line, says, “This guy’s the worst actor I’ve ever seen!” Get it?! That’s Robert De Niro! Amusingly, the performance would garner De Niro his sole Razzie nomination.

18. The War With Grandpa (2020)

Of all the Robert De Niro comedies with the word “Grandpa” in the title, this is absolutely the best one. So, that said, this is a rather dreary “family” comedy about a widower (De Niro) who ends up moving in with his daughter (Uma Thurman!!!!) and has to stay in the same room as his grandson, who very much does not appreciate it. They end up having a “war,” which basically is just a bunch of Home Alone-esque pranks involving shaving cream and poop. The movie is pitched at the level of a mid-tier Disney Channel movie, but it, unlike the other Grandpa movie, is essentially harmless. It does feature Christopher Walken on a skateboard.

17. Last Vegas (2013)

Part of a relatively recent trend of movies centered around the adorable exploits of AARP-aged characters, Last Vegas brings together Michael Douglas, Morgan Freeman, Kevin Kline, and Robert De Niro to play old friends who reunite for a bachelor party in Las Vegas. Coasting on persona like he’s done so often lately, De Niro portrays a widower who hasn’t forgiven best friend Douglas for skipping his wife’s funeral, but he can’t make much of a role that’s been set at “grumpy codger.” Last Vegas is a perfectly fine distraction for five minutes when you’re flipping around the channels on a lazy Sunday. But still, you won’t catch De Niro having much fun or generating many comedic sparks with his equally impressive castmates.

16. Analyze That (2002)

By the time this sequel came out, The Sopranos had been unleashed upon the world, which the movie acknowledges with a couple groaners and a subplot about De Niro’s Paul Vitti serving as a “consultant” on a TV mob show. But the charm of the first film has evaporated here; The Sopranos taking this premise so seriously revealed just how hackneyed this film’s approach to the same material was. In Analyze This, De Niro grounded his mob character in something menacing, but here, he’s just blatantly mugging. You can almost see him, distressed, saying, Is this what you want? You want more of this? The answer would be no, definitely not.

15. About My Father (2023)

We’re at the point of the list where De Niro gets credit simply for not embarrassing himself, and he doesn’t here — which, considering some of the costume decisions writer-director-actor Sebastian Maniscalco makes for his star (he wears more Stars and Stripes than Apollo Creed), is no small feat. De Niro plays Maniscalco’s father (inspired by the comedian’s real-life father), an old-world, very outspoken Italian immigrant hairdresser. Maniscalco (playing “Sebastian Maniscalco”) takes his father to meet his girlfriend’s uber-WASP parents (played by Kim Cattrall and David Rasche), and — you’ll never believe this — they have a series of culture clashes. The comedy here is pretty basic and obvious; Maniscalco goes for the easy joke every time. But there is a sincerity and a sense of good cheer here that’s hard to hate, even when you’re groaning. (And you’ll be groaning a lot.) De Niro is the film’s North Star, and everyone amiably follows the lead of his silly, broad, but nonetheless earnest performance.

14. The Family (2013)

This Luc Besson comedy — there’s a phrase! — has its defenders, but we’re not among them. De Niro is particularly sleepy as the head of a mob family in witness protection that keeps blowing their cover in a charming French village by being inherently brutal and cruel. That’s sort of the whole joke here, and the movie never quite finds the right balance between tongue-in-cheek violence and actual, horrifying violence. De Niro is mostly rehashing old bits, to little effect. There probably is a halfway-decent movie here somewhere, but no one here has any idea where it might be found.

13. The Adventures of Rocky and Bullwinkle (2000)

This long-mocked flop is actually a little bit better than it’s usually given credit for. It’s a meta, self-reflexive comedy before such things were the default mode of communication, and it is aware of own ridiculousness and tries to have fun with it. (The movie, insanely, is written by Kenneth Lonergan, a gig he grabbed after his Analyze This script, though we personally find it funny to imagine it as an early rough draft of Margaret.) De Niro generally acquits himself adequately here as Fearless Leader, but his performance falls closer to the bottom of this list for his self-referencing, “You talking to me?” moment that we still haven’t forgiven him for.

12. The Comedian (2016)

This Taylor Hackford comedy-drama was, of course, the second time that De Niro played a stand-up. But unlike his disturbing turn in The King of Comedy (which, for our purposes, we’re not including in these comedy rankings), The Comedian finds him portraying a slightly more well-balanced comic. He’s Jackie, an aging funnyman who used to be a shocking stand-up before selling out to be the star of a lame family sitcom. Now deep into middle age, and that hit show long over, he wonders what to do both professionally and personally. The movie has a nice, warm glow — your parents are sure to enjoy it — and he’s surrounded by a likeable supporting cast, including Leslie Mann as a potential love interest. But whereas De Niro was supposed to be inept in The King of Comedy, here (where he’s playing a killer comic), he’s just not that convincing. You sense that he’s trying too hard, when the secret to great stand-up is its effortlessness. Away from the stage, though, he’s a sympathetic, engaging presence, even if The Comedian never amounts to much beyond “Older white guy faces existential crisis” banalities.

11. What Just Happened (2008)

As is typical of latter-day De Niro, What Just Happened is just slightly underrated enough that fans make the mistake of overpraising it. Though advertised as a satire of Hollywood wheeling-and-dealing — and inspired by longtime producer Art Linson’s memoir — the film works better as a portrait of a treading-water middle-aged man slowly waking up to the disaster of his life. De Niro plays a beleaguered, high-powered producer juggling two movies that are causing him nothing but headaches, negotiations with two ex-wives, a funeral service, and kids who are growing up too fast. Directed by Barry Levinson, What Just Happened has zero new to say about the industry’s egos and excesses, but De Niro almost makes this dramedy work by underplaying his character’s angst: He’s a deft straight man while all those around him (including Bruce Willis playing a super-diva version of himself) lose their minds.

10. We’re No Angels (1989)

Back in 1989, De Niro and (especially) Sean Penn were so well-established as Serious Actors that casting them in a comedy where they play escaped convicts pretending to be priests was supposed to be self-evidently uproarious. It doesn’t quite work out that way. The main problem with We’re No Angels is that it’s a bunch of deeply serious people (the two actors, screenwriter David Mamet, director Neil Jordan) pulling out everything in their arsenal to prove that they can make you laugh, which causes the movie to feel forced rather than inspired. These men are all capable of making a funny movie, but here they attempt to reverse-engineer one, like they decided to make a comedy without deciding to make it funny first. De Niro’s performance still has aged better than Penn’s, though; Penn seems to be looking side-eyed at the camera, saying, My agents are making me do a comedy, but just so you know, I hate it.

9. Machete (2010)

When De Niro decides to let loose in B-movies, it can be awfully fun. In Machete, he has a ball playing a racist Texas politician who becomes the target of an assassination plot — except it’s actually the politician who’s orchestrating the plot to further his own anti-immigration policy. Robert Rodriguez, who co-directed, always wallows in his pulpy, trashy genre influences, but Machete is one of his better recent efforts, and he’s helped immensely by De Niro’s tongue-in-cheek portrayal. Knowing full well that a boo-hiss villain doesn’t need subtlety, the actor lets his cowboy hat and accent do most of the emoting, creating a wonderfully crude caricature of redneck bigotry.

8. Grudge Match (2013)

The ridiculous premise — two sexagenarian boxers (De Niro and Sylvester Stallone) have a rematch 30 years after their final battle — belies what’s not actually that terrible of a comedy, or at least a wistful one that occasionally generates real emotion. De Niro and Stallone eventually get their moment in the ring, and it’s to De Niro’s credit that he’s not entirely ridiculous, especially standing next to the HGH monster that Stallone has transformed into. Besides, De Niro’s got the better role; his connection with his estranged son who trains him (Jon Bernthal) gives the film its heart. And if you can resist Kevin Hart as the industrious fight promoter and Alan Arkin as Stallone’s ailing trainer trash-talking each other, you are stronger than we are.

7. Analyze This (1999)

Before The Sopranos came and made this movie’s whole approach look absurd, De Niro’s first real financially successful comedy felt like the beginning of a whole new world for him. (As this list attests, it didn’t really turn out that way.) Now, Analyze This is only reasonable effective, but to the extent that it works, it does so on the back of De Niro’s performance. This is before De Niro shamelessly mugged his way through comedies, and here, he makes sure to anchor his Paul Vitti gangster in genuine avarice and fear: It’s a comedy, but you’re meant to be scared of Vitti, and you should be. The sequel was embarrassing, but this one is still pleasant enough, even if The Sopranos’ existence is the worst thing that could have ever happened to this film.

6. The Intern (2015)

Of the many guises De Niro has worn in the movies — antihero, sociopath, street thug — “lovable father figure” has never been one of his staples. So what a pleasant surprise it is to see him in writer-director Nancy Meyers’s predictably cotton-candy comedy, playing a retired widower who reenters the workforce by interning at a trendy online clothing boutique run by Anne Hathaway. The Intern treats De Niro’s character Ben as a bit of a one-dimensional Greatest Guy Ever — always there for some sage advice or a shoulder to cry on — but De Niro imbues the character with such grandfatherly warmth that he’s positively winning. Sweet without being saccharine, the actor makes Ben feel like a refreshing throwback to a chivalrous bygone era when guys were gentlemen and life fit into tidy little categories of right and wrong. As with all of Meyers’s movies, The Intern is a fantasy, but De Niro grounds the proceedings in simple human decency.

5. Meet the Parents (2000)

Easily the most iconic role De Niro has played this century, Jack Byrnes is an ideal role for his deadpan comedic skill-set. Perpetually stoic and endlessly judgmental, Jack embodies the Quietly Disapproving Father-in-Law nightmare that haunts a lot of young men, and De Niro makes it hilarious by not doing much of anything. He doesn’t need to: Ben Stiller’s awkward Greg fills the screen with his nervous flop-sweat, allowing Jack’s silent irritation and withering looks to grow increasingly funnier over the film’s runtime. Meet the Parents is an example of a really clever premise hit out of the park by excellent casting and great setpieces, the film milking our collective memory of De Niro’s violent onscreen history to create a terrific comic tension.

4. Mad Dog and Glory (1993)

This one’s a casting switcheroo, with De Niro playing a meek police photographer who is befriended (and menaced) by a mob boss (Bill Murray) who thanks him for saving his life by “loaning” his girlfriend (Uma Thurman) to him for a week. De Niro is impressively nebbish and nervous here – our favorite scene is when he meets Thurman; he’s so concerned about his appearance that he apologizes that he hasn’t done more sit-ups — and their romance is believable and even a little sad. (Murray’s terrific, too: You have zero doubt that Bill Murray could do horrible things to Robert De Niro if he wanted to.) The movie’s dark and sinister and weird in the right ways, but it also has a hint of the screwball in it: Some of Murray’s mobster henchmen feel like extras out of Guys & Dolls. It also features David Caruso being funnier than he would ever be again.

3. Brazil (1985)

“We needed a hero, and Bobby De Niro was our hero,” Brazil director Terry Gilliam once said of the casting of De Niro in the small but crucial role as Harry Tuttle, the renegade terrorist-plumber in this iconic satire of bureaucracy and government control. “The idea of the hero being a plumber intrigued him because he didn’t like the idea of being a grand figure.” In fact, De Niro got to play Tuttle only after being turned down by Gilliam for the part of the best friend of Jonathan Pryce’s hapless everyman Sam. Nevertheless, De Niro delivered an acting master class on how to create an indelible impression in just a few scenes while underplaying. Both anarchic and witty, Tuttle is so funny because his revolutionary notion is so simple: He just wants to help people with their pipes. Without fuss, De Niro shows off expert comic timing, his ramrod American can-do demeanor a perfect contrast to the largely reserved English cast around him. And especially as De Niro has gotten lazier over time with his broad comedic caricatures, Brazil is a nice reminder of how much he can do with very little.

2. Wag the Dog (1997)

Wag the Dog is notable for several lasts: It’s the last really good Barry Levinson movie, and it’s also arguably one of the last great movies to star either Robert De Niro or Dustin Hoffman. Perhaps you remember Wag for Hoffman’s Oscar-nominated, Robert Evans–channeling performance as a slick Hollywood producer helping to orchestrate a fake war to distract the press corps from a presidential sex scandal. But if you go back and watch Wag now, you’ll notice just how good De Niro is in a less showy role, that of a Beltway operative who seems to speak only in double-talk. Projecting preternatural confidence and a shit-eating grin that suggests his character, Conrad Brean, knows he’s smarter than you, De Niro revisits the spiritual terrain of The King of Comedy’s Rupert Pupkin — except, this time, he’s not deluded in his surety. A forgotten gem of the Clinton years, Wag the Dog is a great political comedy, and De Niro’s understated performance holds the film together.

1. Midnight Run (1988)

In Midnight Run, on-the-lam accountant Jonathan Mardukas (Charles Grodin) informs sullen L.A. bounty hunter Jack Walsh (De Niro), “You have two forms of expression: silence and rage.” It’s a great line — and it encapsulates De Niro’s comedic aesthetic, especially in this, his best comedy. The trick to Midnight Run’s hilarity is that deep down, it’s not really that funny of a movie: Our mismatched protagonists are stuck on a perilous cross-country trek from New York to Los Angeles while hit men, mobsters, the FBI, and a rival bounty hunter are all after them, many of their pursuers wanting them dead. Accordingly, De Niro doesn’t play the material for laughs, which is why his interactions with the wonderfully deadpan Grodin are so damn funny, Mardukas’s blasé manner consistently irritating the easily wound-up Walsh. Like many of the best comedies, Midnight Run actually gives De Niro a character to play — Walsh is a good egg who got run out of the Chicago police force because he alone wouldn’t take bribes from the mob, losing a wife and daughter in the process — and the actor brings a sweet decency to the role while also masking it with the character’s tough-guy act. The mannerisms and self-parody that would become a staple of De Niro’s later comedic work are nowhere to be seen here, his slow fuse never more confidently implemented than counter to Grodin’s fiendishly subtle needling. Perhaps even better, nobody ever got the bright idea of ruining the memory of this 1980s classic by trying to do a sequel.

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