I’m not sure what made me want to spotlight mafia comedies, but I want to. I really want to! The “mafia comedy” is a perfect subgenre. It spoofs a genre which is so perfectly exaggerated in its drama that it is ripe for spoofing! In this way, I find something liberating about a mafia comedy; then again, I always love it when a dramatic genre bursts out with something comedic.
Well, anyway, fam, in case you want your guns full of flags that say “bang” rather than bullets, like me, here are fifteen bang-up mafia comedies for you.
Now, is this list ranked? No, because this is a list about the mob, and I don’t want anybody to come after me. So this list is more of a POOL than a ranking.
Is anything missing? There are a few I left out. I’ve never seen Oscar, a movie google tells me exists. Additionally absent from this list is the 1976 musical comedy film Bugsy Malone, a gangster saga exclusively starring children, in which a 13-year-old Jodie Foster plays a gangster’s moll. I saw it as a kid and do not remember enjoying it.
Okay, I think that’s it. Let’s go to the mattresses, or the couches, or the Lay-Z-Boys, or whatever comfy surface you prefer to rest on while you watch something fun.
Andiamo!
Married to the Mob (1988)
Michelle Pfeiffer stars in this adorable Jonathan Demme film about a mafia wife who hopes for a fresh start after her mobster husband (Alec Baldwin) gets whacked. But a tryst with an FBI agent (Matthew Modine) and her ties to the local mob kingpin (Dean Stockwell, RIP) compromise her plans for freedom. Also, Mercedes Ruehl plays Dean Stockwell’s crazy wife in this, and she is incredible.
The Freshman (1990)
Ah, The Freshman, in which Marlon Brando parodies his most famous role. Matthew Broderick plays a young film student who partners up with a mobster who looks a lot like Don Corleone, but things take a turn when the mobster, well, makes him an offer he can’t refuse.
The Whole Nine Yards (2000)
Matthew Perry and Bruce Willis star in this incredibly charming comedy about a hapless dentist and a wild-eyed mob hitman-turned-informant-in-hiding (do I need to add “respectively”?) who wind up as neighbors in suburban Montreal. And who steals the show but Amanda Peet? Whole thing is a HOOT.
Get Shorty (1995)
Get Shorty is the timeless tale of a mobster who heads to Hollywood to collect a debt and finds out that La La Land is just as cutthroat as Mobland.
My Blue Heaven (1990)
My Blue Heaven, Nora Ephron’s mob comedy about a gangster in Witness Protection, is a strange film. Often considered the spiritual sequel to her husband Nicholas Pileggi’s film Goodfellas (and its source text, Wiseguy), it’s the tale of a straightlaced FBI agent (Rick Moranis) who has to look out for Vinnie Antonelli (Steve Martin), an ebullient and friendly mobster sticking out like a sore thumb in witness protection.
Johnny Dangerously (1984)
Amy Heckerling’s NUTSO mafia spoof Johnny Dangerously is one of the best movies on this list. And, FYI, it is cruelly being withheld from all viewing options by a bunch of *fargin iceholds* (a reference you would get if you could WATCH Johnny Dangerously, which you probably can’t unless you have it on DVD). Long live physical media! And long live Johnny Dangerously!
Mafia! (1998)
What is it about the nearing-millennium that made everyone want to make a mafia comedy!? All the gold-lamé tablecloths? The prestige of The Sopranos? Anyway, this Lloyd Bridges-helmed comedy is a sendup of The Godfather, about a young man who attempts to replace his dying father as the head of the mob. A favorite of CrimeReads editor Molly Odintz.
Friends and Romans (2014)
This is an adorable indie comedy about a bunch of Italian-American New York actors who are tired of getting typecast as mafioso types, so decide to put on a production of Julius Caesar to show what they can really do… only, in attempting to rent a venue, that’s when they get mixed up with the actual mob without realizing it, and get a bunch of FBI agents on their case. It’s very cute. It features a LOT of Sopranos alums. (Also, full disclosure, my husband plays the FBI agent who figures out what’s going on.)
Bullets Over Broadway (1994)
Bullets Over Broadway, the classic story of a mobster with theatrical ambitions! Personally, I find it hard to enjoy Woody Allen movies, knowing what we now know about him, but maybe you can handle it.
Mickey Blue Eyes (1999)
Mickey Blue Eyes is the funniest film on this list, and it breaks my heart that it’s not streaming. Hugh Grant plays a sweet and bumbling English fine art auctioneer in New York who falls in love with the estranged-ish daughter (Jeanne Triplehorn) of a notorious mob family. She makes her fiance promise not to get involved with her family, but soon her gangster dad (James Caan, perfection) winds up enlisting him when the family makes an offer he can’t refuse.
Midnight Run (1988)
Is Midnight Run, the 1988 buddy-crime-comedy Midnight Run starring Charles Grodin as a do-gooding embezzler and mob accountant captured and dragged across the country by bounty hunter Robert DeNiro, the greatest road trip movie of all time? Yes. Watch it with your best friend, OR your worst enemy. Points if they’re the same person. Also, wow, how many times is Dennis Farina on this list?
Honeymoon in Vegas (1992)
Also, James Caan! How many times is James Caan on this list! Honeymoon in Vegas is the story about a commitment-phobic P.I. who decides to take the plunge and go with his girlfriend Sarah Jessica Parker to Vegas to get married… when he meets gangster James Caan, who becomes obsessed with SJP and stymies Nicolas Cage’s whole plan.
Analyze This (1999)
Analyze This is a solid, comic Sopranos-contemporary that goes down as smooth as a salty red sauce (as in, it’s fine while you’re experiencing it but it WILL give you heartburn later). Robert De Niro and Billy Crystal have very good chemistry as a mob boss and a neurotic shrink, respectively, who wind up thrown together. You would think the movie would be better, somehow, with a script from Kenneth Lonergan and the top-notch prowess of its two leads. Maybe it’s because, implausibly, Billy Crystal’s character is supposed to be getting married to Friends-era Lisa Kudrow, a match that makes no sense even to the criminally insane.
Prizzi’s Honor (1985)
Prizzi’s Honor!!!! Anjelica Huston won her Academy Award for this film, the final movie her father John Huston directed! As if that’s not Family Business enough… Prizzi’s Honor is about a Brooklyn-based, Italian-American mob hitman for a famed New York mafia family, who falls in love with a beautiful non-Italian lady assassin from California. It only gets wilder from there.
Some Like It Hot (1959)
Some Like It Hot may very well be the best film comedy of all time. I hope no one reading this website doesn’t know the plot of this film, but just in case… it is the story of two musicians, Jerry (Jack Lemmon) and Joe (Tony Curtis) who witness a mob execution and go on the run, disguising themselves as women and joining a traveling all-female jazz band headed to a residency at a Florida hotel. Marilyn Monroe is the lead singer of this band. Thus… madness ensues.
