10 Great Gangster Comedies You May Have Never Seen

5. You Kill Me (2007)

Now we’re coming into little more serious mafia comedies after mentioning somewhat sillier ones. There’s a bit of humor in John Dahl’s best works – “Red Rock West,” “The Last Seduction,” you name it – and he finally made a total comedy crime with “You Kill Me,” a very dark and entertaining movie. Ben Kingsley hadn’t gotten a great part since “House of Sand and Fog,” and it’s one of his finest turns in the 21st century; he gives an understated performance and gets the film’s humor so well that he becomes amusing to watch as a hit man with a drinking problem. Very authentic and his facial expressions always let the viewer know what is going on in him without having to say anything.

The supporting cast has their own appeal as well; Luke Wilson, Bill Pullman, and particularly Tea Leoni, whose warm presence is missed in movies these days. Another familiar name was the late Dennis Farina, who’s always in some of those movies, be it “Midnight Run,” “Get Shorty” or “Snatch”. The thing is, even if it didn’t have the humor it has, the movie would still work as a solid drama, but luckily it has a lot of interesting character work and lots of humor.


4. Things Change (1988)

Mafia comedy in David Mamet style and a surprisingly strong friendship story with two very interesting characters at its center. This clever and funny film is about a shoeshine man Gino (Don Ameche) who gets an offer from Chicago’s Italian mafia to do the time for a murder he didn’t commit, and in return, they’ll buy him a fishing boat in Sicily. Gino is assigned to Jerry, a younger syndicate underling (Joe Mantegna), whose job is to guard him over the weekend until he can confess on Monday. Jerry gets bored with the whole situation, so they go to Tahoe for the weekend and things get out of control.

There’s a bit of ‘40s noir influence on Mamet’s handling of the material and from a writing standpoint, the dialogues are expectedly well-written. The performances are also top notch and the film finds a wonderful balance between comedy and drama; it’s less slapstick than many other films on the list but it has a lot of funny moments, as it has thoughtful moments as well.


3. Married To The Mob (1988)

Married to the Mob (1988)

Okay, this is almost a classic to some degree. So how is this underrated? Well, it feels like it doesn’t get talked about much recently and even its audience scores aren’t that great anymore, which is certainly strange because it’s just a delight from start to finish. It’s amazing how versatile Jonathan Demme was. He made this, and he made “Something Wild,” then “The Silence of the Lambs” and “Philadelphia.” Sometimes it feels like he didn’t get enough recognition for his versatility, and Michelle Pfeiffer is simply brilliant in the lead role here.

Pfeiffer herself considers it among her own favorite performances. She plays Angela, the pretty widow of a mafioso, who not only catches the eye of the godfather of her clan, but also of the FBI who are conducting surveillance, and also of Tony’s wife Connie, who repeatedly confronts Angela with accusations of stealing her husband. Because a clumsy agent falls in love with the woman, the surveillance planned by the general staff threatens to fail. Things get more complicated later on and the film avoids the clichés and gives us a great screwball comedy, with a complex heroine who tries to get her freedom and playful tone that keeps you engaged and amused.


2. Bullets Over Broadway (1994)

Bullets Over Broadway

The idea of a Woody Allen persona dealing with the mob is always funny and that’s why he used this idea well in some of his movies, including “Broadway Danny Rose.” As for the next film on the list, “Bullets over Broadway,” despite its recognition, this one is slightly underrated. Sure, it’s in fact one of the most recognized films on the list and made into several year-best lists of critics, but you don’t hear this one named among Allen’s classics – but it has every element to be considered as one. In this comedy, the worlds of mafia and theatre industry goes in a mix.

Playwright David (John Cusack) wants a socially critical drama. His manager gets money from the mafia, but the mafia wants his lover Olive (Jennifer Tilly) to have a part in it. Then another gangster named Cheech (Chazz Palminteri) gets involved, who is perhaps a better writer than David actually is. The performances are very enjoyable, and three of the main cast members got an Oscar nomination for their work; the only exception being John Cusack, whose snub is understandable given how stacked the category was that year. Allen’s writing is sharp, the pace is fast, and the film is just sublime entertainment.


1. Mafioso (1962)

It starts out like “Meet the Parents” but ends like “The Godfather”; this movie is a brilliant work from Italian film director Alberto Lattuada. The lead character, Antonio Badalamenti, is a Sicilian man with better luck than most; he’s employed in a car factory in Milan as a factory supervisor and now it’s time for him to take a vacation with his family. He decides to visit his childhood village in Sicily. While there, he also visits the local Don Vincenzo. Things turn out in a way that now Antonio is tasked with carrying out a hit for the mob.

Relevant today as it was then, “Mafioso” is certainly a very underrated film. It has a wonderful balance between the tones that may surprise some viewers; as it’s mentioned, it starts out like a comedy that turns into something serious after a point, but it feels it in such an organic way that you don’t mind it all. Indeed, it becomes fascinating to watch. The movie works as a comedy, as a drama, as a social critique on so many levels. Unfortunately it didn’t get much attention when it was released and maybe it’s because it was way ahead of its time. The direction is very impressive, the camera work keeps you engaged (shot in gorgeous black and white), the music is exceptional, the setting is authentic, and performances are top-notch. Cinematographer Armando Nannuzzi certainly did exceptional work at creating such rich atmosphere. It’s never too late to give this great film the recognition it deserves.