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The Funniest Mobster Comedies Ever Shot

Photo-Illustration: Vulture. Photos: Ronald Siemoneit/Sygma; Tri-Star; MGM

Movie formats definitely go through trend cycles. Beyond the Dante’s Peak/Volcano of it all, there are waves of subgenres that have their day then fade away. Zombie movies in the aughts are one example, as is the endless stream of superhero fare today. Gangster comedies have had at least two waves: one in the late ’80s and early ’90s that share DNA with “weird New York” films like After Hours and coincided with the surprisingly funny drama Goodfellas and unintentional comedy The Godfather Part III. Then another spate of films dropped just a decade later around the time The Sopranos came to HBO. With Mafia Mamma in theaters now, are we due for another mini-wave of crime comedies? And if so, will they be any good?

Filmmakers create crime comedies because the stakes are already at life and death. For the same reason Michael Scott wanted to pull a gun in every improv scene, mob comedies work: It’s immediate emotional investment. And things can only get crazier from there. Then there’s the reality that everything most audiences know of the criminal underworld they learned from movies. We are more likely to encounter cartoon mob bosses than the real thing, and that’s where most of these movies live — in a live-action cartoon space.

We ranked these mafia/yakuza/British gangster comedies on one sole criterion: Is it funny? Mob comedies can offer many charms. Audacious accent work, Tony Bennett needle drops, well-plotted capers. Vulture cares not for these things. We are here to recommend movies that will make you fuggedabout your troubles and laugh. When deciding which of the movies were funniest, we looked at jokes per minute, comedic heightening, and how cartoony events got. The best of them turn the real world (usually New York and/or Miami) into fantasyscapes that Bugs Bunny would feel right at home in. Leave the gun, take the jokes.  


Mickey Blue Eyes (1999)

Of the Analyze This also-rans, Mickey Blue Eyes is the only “average Joe runs afoul of a Godfather actor” film to have Hugh Grant at his peak charm. Jeanne Tripplehorn also delivers a great performance, but this rom-com is hampered by the outdated attempt at a neurodivergent character played by Paul Lazar. That, and a plot a little too convoluted for even a mob comedy. Hugh Grant is roped into money laundering by his would-be father-in-law (James Caan). But when an art auction goes wrong and a mobster ends up dead, the family decides to take it out on Grant. This leads to plots within plots, FBI informants snitching on themselves, and a less than successful grand finale. Fun to see most of the cast of The Sopranos, though.


My Blue Heaven (1990)

Now that they let Italians be in movies, do we really need this desperately miscast Steve Martin vehicle? My Blue Heaven is interesting for its provenance. Both it and Goodfellas, which was released in theaters the month after this comedy, are based on the life of Lucchese crime-family mobster turned FBI informant Henry Hill. Both My Blue Heaven writer Nora Ephron and her husband Nicholas Pileggi (who wrote the book on which Goodfellas is based) interviewed Hill and came up with their stories from the same sessions. Unfortunately, noted non-comedy Goodfellas is funnier. This may be because Ray Liotta plays Hill as someone worth centering a movie on. Steve Martin’s fish-out-of-water gangster living in the witness protection program is barely worth a SNL sketch.


Skidoo (1968)

It’s hard to tell whether you’re laughing with or at Skidoo, an attempt at a counterculture comedy starring Jackie Gleason, Carol Channing, Frankie Avalon, and Groucho Marx. Marx plays mobster “God,” who commands Gleason’s hit man Tony Banks to do one last job and take out former BFF “Blue Chips” Packard (Mickey Rooney). But then Tony’s daughter joins some weird hippies, God goes on the run, and there’s an acid trip in jail. It’s a lot, and not all of it works, but what a film to put on mute at a bar! You’d miss the Harry Nilsson soundtrack, but you’d possibly attain nirvana.

Available to stream on Plex


The Freshman (1990)

There’s a lot to recommend The Freshman as a film. It’s sweet to watch endangered-animal smuggler Marlon Brando and his naïve runner Matthew Broderick grow fond of each other. Penelope Ann Miller 100 percent serves cunt as mafia princess Tina Sabatini. And the ending set piece at a supper club for eating endangered species is something else. It’s not “monkey basketball” episode of SVU–level crazy, but it’s sufficiently whimsical. But jokes? Not so much. One of the running gags in the movie is people’s incredulity at how much Brando’s mobster resembles Vito Corleone. It falls flat the first time and only gets worse with repetition. The Freshman is also oddly sleepy for a movie that co-stars a Komodo dragon. But if you want to see Broderick essentially playing Cameron instead of Ferris Bueller, this is for you.

Available to stream on Showtime


 Analyze This (1999)

Analyze This makes a good argument that adhering too strongly to masculine ideals is a mental illness. You can’t have feelings, because you must display strength at all times. And you don’t have any true fellowship. Your tough-guy peers can’t emote, either, and the women in your life aren’t respected enough to be real confidants. It’s horrifically lonely. But anyway, comedy! Most of the humor in Analyze This comes from the culture clash between stoic mobsters and touchy-feely therapyspeak. Mob boss Robert De Niro becomes a patient of Billy Crystal’s psychiatrist against Crystal’s will, following him across the country to get advice on how to manage his panic attacks. Analyze This manages to ratchet up the comedic tension and strengthen the emotional bond between De Niro and Crystal enough that their friendship remains believable through the sequel. But it’s a true double-hander, which means Lisa Kudrow, who plays Crystal’s fiancée, is criminally underwritten and underused. If anyone besides Crystal, De Niro — and, to a lesser extent, Joe Viterelli — got any room to flex, this film would be higher on the list.


Snatch (2000)

Guy Ritchie movies are always balancing balls-to-the-wall action with comedy. How can you build tension again unless you’re also constantly deflating it with jokes? Here, underrated comedic performer Jason Statham (sequels for Operation Fortune, please!) is the center of a widening gyre of violence in the British underworld. An 86-carat diamond becomes the film’s MacGuffin, traded back and forth between gangsters as fight promoter Statham tries to get out from under the thumb of a guy named Brick Top. Ritchie builds his movie on a foundation of sand, and it’s satisfying to watch the whole thing fall apart. We also get acknowledgment of the Jewish mob, thanks to Dennis Farina’s Cousin Avi. It’s the same kinetic energy of Lock Stock and Two Smoking Barrels, taken to 11 and with an incomprehensible Irish-accented Brad Pitt to boot.

Available to stream on Peacock


Connie and Carla (2004)

Toni Collette, what are you doing here? Before Mafia Mamma, Collette starred opposite My Big Fat Greek Wedding’s Nia Vardalos in this adorable drag-mafia comedy. Is it a retread of Some Like It Hot? Yeah, kinda. But with a little Victor Victoria thrown in, as Vardalos and Collette hide from the mob by pretending to be drag queens rather than pretending to be male-presenting men. Plus, Debbie Reynolds is here! We love her. The scenes where the mobsters go to regional production after regional production of Mame and slowly fall in love with live theater? Gorgeous, heartwarming, life-affirming.


Zatoichi (2003)

Most of this list focuses on Italian mob comedies, as that’s the crime syndicate the American moviegoing audience knows best. And almost all of them focus on the 20th century. Zatoichi is a jidaigeki, or Japanese period film, about a blind swordsman facing off against the local yakuza. Directed by comedian turned gangster auteur Takeshi Kitano, the film uses both sides of his personality to the fullest. The violence is grim and bloody, but the jokes are slapstick and dumb as hell. There’s a character we’d now read as trans who is treated with great respect and a soundtrack performed by a STOMP-like band of peasants. A criminally underrated showcase of physical comedy, the film is Yojimbo meets the Marx brothers.


Desperately Seeking Susan (1985)

Susie Seidelman also directed the funny and underrated 1989 mob comedy Cookie, which is even more mobster-y than Desperately Seeking Susan and features Peter Falk. However, Cookie is vanishingly hard to find, while Desperately Seeking Susan is both available to stream and so, so fun. Rosanna Arquette stars as a New Jersey housewife who goes through a midlife crisis after coming into possession of a coat belonging to Susan (Madonna). Through the coat, she’s roped into the murder of mob hit man Bruce Meeker and the theft of Egyptian earrings. It’s one of those movies that sets a very particular version of New York in amber — along with After Hours, Times Square, and Married to the Mob (more on that later). It’s funny, gorgeous to look at, and a ready-built Pinterest board for fashion and interior-design ideas.


In Bruges (2008)

Before Jenny the Donkey, there was Jimmy the little-person thespian. In Bruges was the first pairing of Colin Farrell and Brendan Gleeson under the direction of Martin McDonagh. The pair play Irish hit men hiding out in Bruges while their boss (Ralph Fiennes) decides the fate of Farrell. A Vantablack comedy, In Bruges is one of the few on this list where the mob isn’t softened. The sympathetic protagonist isn’t trying to retire after a life of unspecified crime. The crimes are specified, and there’s no way out.

Available to stream on Starz


Some Like It Hot (1959)

I almost didn’t include Some Like It Hot, because the mob only comes in and out of the film. Your brain doesn’t classify it as “mob movie”; rather, it’s a “Marilyn Monroe film” or a “cross-dressing comedy” or even just “black-and-white.” But it’s of a select number of older comedies that have kept their punch over the decades. (Come to think of it, a lot of well-aged comedies are directed by Billy Wilder.) Jack Lemmon and Tony Curtis join an all-woman jazz band because they accidentally witness a gangland massacre around Valentine’s Day — which is legally distinct from the real St. Valentine’s Day Massacre, you got that? Monroe gives one of her last great comedic performances in the film, and the queer themes can’t help but shine through despite the Hays Code.


Get Shorty (1995)

A perfect combination of Florida weird with L.A. sleaze, Get Shorty somehow stays funny while also being incredibly cool. This adaptation of Elmore Leonard’s novel is a cynical love letter to Hollywood, bringing the best parts of mob comedies and movies about movies to the table. Under Barry Sonnenfeld’s direction, John Travolta’s loan shark trying to pivot to film production, “Chilly,” is exactly that — chill as fuck. Unflappable, despite both movie types and rival mobsters desperately trying to flap him. On an unrelated note, why does Get Shorty have the same poster as another Sonnenfeld joint, Men in Black? Something to think about.


Married to the Mob (1988)

So many mob movies resign the mafia wife to a few lines about jewelry and mink coats or whatever Mobster Jr. is getting up to. Married to the Mob goes the complete opposite direction, making Michelle Pfeiffer’s reluctant widow almost the only sympathetic character. When her gangster husband is killed by his Don (Dean Stockwell), she tries to go legit on the Lower East Side. But she’s harassed by the Don, harangued by his wife (Mercedes Ruehl), and surveilled/courted by an FBI stuffed shirt (Matthew Modine). As the Blank Check podcast pointed out, it’s such a Jonathan Demme move to center a mafia movie on a woman’s point of view. But what makes Married to the Mob the best is that it’s the most quirked-up freak fest this side of Pee-Wee’s Big Adventure. There’s doo-wop groups, Rube Goldberg dressing machines, and Demme’s always bonkers framing choices. It leans into the absurdity of mob movies and paints the government as being equally corrupt/laughable. Married to the Mob makes you salute everyone involved for being too weird to exist in any other movie.

The Funniest Mobster Comedies Ever Shot