10 Great Gangster Comedies You May Have Never Seen

There was a time in cinema where crime films, particularly mafia and gangster related films, were way more common than they are now. Nowadays, you only get the Russian mafia as a villain in your actions. In those days, we also got a lot of comedies that mocked those too tough, too evil or too serious sides of characters in those gangster movies.

There were different kinds of them; many of them were parodies, but some were working both as an actual average crime drama story and a comedy simultaneously. There were satires that put a gangster in the center of different universes (like “Get Shorty”), there were direct spoof parodies (“Jane Austen’s Mafia!”) and then there are things like “Analyze This,” where the mafia man had to get therapy.

Let’s take a look at 10 such films that are mostly underrated; some actually got a good amount of attention when they were first released, but recently it seems they’re not talked or discussed enough.


10. Wise Guys (1986)

Brian De Palma is perhaps best known for his suspense thrillers, but he has also made some of the best-known crime dramas of their respective decades, such as “Scarface,” “The Untouchables” and “Carlito’s Way.” They all are different from each other, which is probably why it’s not a surprise that he took on a mafia comedy genre as well in “Wise Guys,” one of his lesser-known but somewhat lovely comedies.

This unusual entry in his filmography follows Henry Valentini (Danny DeVito) and Moe Dickstein (Joe Piscopo). They’re best friends and have known each other since childhood. They also work for the mob, but for small stuff, like taking laundry. One day they’re supposed to bet on a horse; their boss always bets on the same horse, and always loses. So they decide to bet on a supposed favorite; things go wrong, they lose, and now they’re ordered to be killed. The rest is a lot of situation comedy. Kind of an old-school comedy film, bit over-the-top at times but still light-hearted; you find the lead characters sympathetic enough to root for them or care about them. The ending is great as well. It has authentic New Jersey locations and there’s also a classy turn from Harvey Keitel as well, his only appearance in a De Palma movie. De Palma’s Springsteen love also shows itself in one very fine sequence.


9. Mickey Blue Eyes (1999)

This one got a lot of mixed reviews, which is strange. While it’s not some comic masterpiece, it’s not the type of film that one would necessarily criticize for its plot going to silly places, or the premise being not fresh or inspired enough. The film was made only for entertainment; whether or not the humor works for you is a different topic, but it’s not a film that claims to have some smart premise or original storyline. Looking back, it didn’t age badly, and it has a lot of ‘90s charm.

Hugh Grant plays a character similar to his “Four Weddings” persona, a bit more confident but still this British gentleman who falls in love with an American woman who happens to be a daughter of a gangster. That’s basically the premise – putting a guy like him in the front of all of these situations and making us laugh. Grant’s comic timing is well known and he recently returned to the gangster world with a brilliant performance in “The Gentlemen,” which is a totally different kind of character in comparison. The other funny guy here is James Caan, the man who starred in “The Godfather.” Even though in some countries it got a lot of TV airings over the years, this unfortunately flopped at the box office, maybe because “Analyze This” was very fresh on people’s mind and people didn’t care to see another gangster comedy in such a short time.


8. The Freshman (1990)

The Freshman

A new student at the New York film school is unexpectedly elevated to a member of a mafia family and thus a key figure in a prearranged game about rare animals, dubious specialty restaurants, wildlife protection, and fake agents of the FBI. James Caan has once mentioned in his “Inside the Actors Studio” interview that his “Mickey Blue Eyes” performance was slightly a parody of his “Godfather” performance.

In “The Freshman,” though, Marlon Brando makes a very obvious parody of his “Godfather” role and the result is truly hilarious. A rare chance for him to be actually funny, even if his screen time is limited. No worries about that, since the rest of the movie is pretty fun as well; one wonders what happened to director/writer Andrew Bergman, who also wrote another underrated rom-com around that time titled “Honeymoon in Vegas.” Does the whole thing make much sense? Who cares? We’re here for fun and it’s certainly a fun ride. Matthew Broderick’s charming lead performance also brings a lot of emotional honesty to the whole thing.


7. Johnny Dangerously (1984)

Amy Heckerling has directed two of the most popular teen comedies of all time in “Fast Times at Ridgemont High” and “Clueless,” but her attempt at gangster comedy is not mentioned enough and it’s everything you would want from a film like this. It’s a charming homage to 1930s gangster films, starring Michael Keaton in a very delightful performance as an honest man who goes to the dark side to pay his mother’s bills. The premise is not important here anyway, since the film is mostly a parody of the genre; if you’re familiar with the films of the ‘30s and ‘40s, such as “Scarface,” “Manhattan Melodrama,” “White Heat” and “Public Enemy,” then the movie becomes funnier for sure.

It’s not just Keaton, the supporting cast is great as well and we have some truly funny supporting characters here. The pacing is fast, it never has a dull moment, it has a lot of fine one-liners and witty jokes. No wonder Mel Brooks made a reference to it in his “Robin Hood” parody because this actually comes off like a Mel Brooks film. There are outdated moments and this may feel like a series of gags instead of an actual film with a plot, but if you’re in the mood for this, it’s a lot of fun.


6. My Blue Heaven (1990)

Those were the times when gangster films were truly common. The year 1990 saw the release of the last part of the “Godfather” trilogy, Abel Ferrara’s indie hit “King of New York” and Martin Scorsese’s crime masterpiece “Goodfellas,” and here comes a movie that actually is a fine companion piece to “Goodfellas” (as strange as it sounds) because both films are actually about Henry Hill. The films’ respective writers, Nicholas Pileggi and Nora Ephron, were husband and wife.

However, Ephron’s screenplay goes a totally different route. Our main character, played by Steve Martin, is in a witness protection program. He lives in the suburbs and has no intention of leaving crime behind, which causes some problems for our other main character, the FBI agent portrayed by Rick Moranis. Martin’s performance is amusing but it’s not one of his best works; Moranis and Joan Cusack’s storyline feels more real to the tone the film goes for. Released a little over a month before “Goodfellas,” this film ended up being forgotten over the years, but it’s a witty and amusing film.