One of the beautiful things about the crime movie genre is how chock-full it is of very distinct, yet equally entertaining subgenres. Since the days of Classic Hollywood, however, one of the most popular and prolific has been the gangster genre. These are movies focused on characters from gangs, mobs, and other kinds of organized crime. From The Godfather to Goodfellas, some of the best films of all time are gangster films.
What’s much rarer — and therefore, in a way, much more precious — are gangster comedies. After all, laughs and jokes are probably not the first thing that comes to mind when one thinks about the tropes of the gangster genre. However, a few hilarious gems like Midnight Run and In Bruges have proved over the course of the years that mobsters don’t need to be broody: They can be funny, too.
10 ‘The Freshman’ (1990)
Directed by Andrew Bergman
One of the most underrated satire movies of all time, The Freshman stars Matthew Broderick as a New York film student who takes a job with a local criminal who resembles a famous cinema mob boss. He takes the young man under his wing in exchange for total loyalty. Who plays the mob boss in question? None other than Marlon Brando himself, in what’s probably the best of his precious few comedic roles.
More than just a smart parody of The Godfather, though (which, make no mistake, it absolutely is), The Freshman is an excellent comedy in its own right. Anchored by the terrific casting of the two lead roles, it also shines thanks to Andrew Bergman’s zany direction and a breezy pace. The story is certainly not without its dead spots, and the gimmick of the parody may wear a bit old for some after a while; but for those who enjoy gangster comedies, this is a must-see.
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9 ‘Analyze This’ (1999)
Directed by Harold Ramis
Image via Warner Bros.
Analyze This is one of the most iconic crime comedies of the ’90s, about a psychiatrist whose number-one patient is an insecure mob boss. With Billy Crystal and Robert De Niro at the top of their comedic games in the lead roles, this high-concept comedy mixes (often highly profane) humor with explosive bursts of mafia-related action, making for one of the most entertaining films of its type.
“It’s a creative and highly amusing comedy whose expertly hilarious cast manages to make even the weaker jokes land.”
Analyze This tends to fall victim to quite a few of the gangster movie genre’s clichés, causing its script to miss the mark in a few respects. For the most part, though, it’s a creative and highly amusing comedy whose expertly hilarious cast manages to make even the weaker jokes land. The late Harold Ramis made a few of the funniest and most memorable comedies of his time, and this is one of his strongest works as a director.
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8 ‘Bugsy Malone’ (1976)
Directed by Alan Parker
Image via Paramount Pictures
A spoof of Prohibition-era gangster films, Bugsy Malone is a family musical about the rise of mobster Bugsy Malone and his battle for power with other crime bosses. The twist? All the gangsters are played by children who, instead of real guns, shoot splurge guns that cover the victim in whipped cream. It’s certainly a goofy premise, and the movie knows it, going on to use it in the most delightfully quirky ways.
British director Alan Parker was arguably one of the most versatile filmmakers who ever lived, which is proved by movies as unique as Bugsy Malone. Kids are sure to have a blast with its story, but grown-ups familiar with the gangster genre are guaranteed to have a blast as well. Thanks to its cute premise and all the amusing ways in which it’s used, it’s one of the most charming crime comedies of the ’70s.
Bugsy Malone
Release Date September 6, 1976
Director Alan Parker
Runtime 93
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7 ‘Get Shorty’ (1995)
Directed by Barry Sonnenfeld
Image via Metro-Goldwyn-Mayer
John Travolta, Gene Hackman, Rene Russo, and Danny DeVito star in this dark comedy about a mobster traveling to Hollywood to collect a debt, where he discovers that he might just be a natural for the movie business. The star-studded cast is far from the only strength of Get Shorty. One of the best John Travolta movies, this is as much of a smart satire as it is a crime comedy that stands on its own two feet more than well enough.
The stars are hilarious, Barry Sonnenfeld’s direction is full of personality, and all the twists that the witty screenplay puts on the genre are a delight to see. With clever, sharp dialogue and some of the funniest gags in any gangster comedy, Get Shorty is as thrilling as it is funny, as offbeat as it is refreshingly familiar, and as underrated as it is incredible.
Get Shorty
Release Date October 20, 1995
Runtime 105
6 ‘Midnight Run’ (1988)
Directed by Martin Brest
Image via Universal Pictures
Starring De Niro and Charles Grodin at their absolute funniest, Midnight Run is a late-’80s comedy classic about a bounty hunter pursuing a former mafia accountant who’s also being chased by a rival bounty hunter, the FBI, and his old mob boss. Cat-and-mouse crime movies are always fun, but with the added twist of smartly-written jokes and cleverly-constructed gags, the result is even more entertaining.
The De Niro and Grodin duo — namely, their chemistry and the way they hilariously bounce off of each other — is perhaps the main reason why Midnight Run is so timeless. However, it deserves a lot more praise as a terrific comedy in its own right. A buddy movie full of adventure, comedy, and road trip movie tropes, it’s an irresistibly fun film that keeps a tight grip on the audience’s attention for over two hours.
Midnight Run
Release Date July 20, 1988
Director Martin Brest
Runtime 126
5 ‘Zatoichi’ (2003)
Directed by Takeshi Kitano
Outstanding gangster movies — including gangster comedies, of course — are made outside Hollywood, too. Such is the case of 2003’s Zatoichi, one of the most underrated samurai movies and arguably one of the best adaptations of the famous character created by novelist Kan Shimozawa, who’s been transported to the silver screen an impressive number of times. It’s the tale of a blind masseur who also happens to be a swordsman. He arrives at a town in control of warring gangs and a powerful samurai, where violent showdowns await.
With riveting samurai action, a colorful narrative full of absurdist comedy, and idiosyncratically directed by Takeshi Kitano, this version of Zatoichi is an epic period piece with showstopping combat sequences, intelligent humor, and even a healthy dose of tap-dancing. It’s a welcome update of a legendary story and character essential to Japanese pop culture; one which movie fans from all around the world should be able to appreciate.
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4 ‘Snatch’ (2000)
Directed by Guy Ritchie
Image via Screen Gems
Guy Ritchie tends to be a pretty hit-or-miss director; as such, he’s arguably one of the most divisive working today. Near the start of his career, though, he was an outstanding up-and-coming British director with two surefire modern classics under his belt. His second movie, Snatch, is a caper where unscrupulous boxing promoters, violent bookmakers, a Russian gangster, incompetent thieves, and Jewish jewelers fight to track down a priceless diamond.
Snatch is one of the best sophomore directorial efforts of the 21st century thus far, as well as one of the greatest gangster movies of the 2000s. It just so happens that its engrossing crime narrative is coated in highly effective dark humor, making viewers laugh out loud just as often as they sit on the edge of their seats, biting their nails in suspense.
Snatch
Release Date September 1, 2000
Runtime 103
3 ‘In Bruges’ (2008)
Directed by Martin McDonagh
Image via Focus Features
With only four movies under his belt (and counting), Martin McDonagh could very well already be considered one of the best comedy directors of all time. It’s all thanks to movies like In Bruges, his brilliant directorial debut. With pitch-black humor and surprisingly existentialist themes, it tells the story of two hitmen who, after a job gone wrong, have to lie low in Bruges, Belgium while awaiting orders from their ruthless boss.
While not one’s typical gangster comedy in any way, In Bruges nevertheless is able to find its cozy home in the genre. Nestled there, McDonagh is able to craft a powerful yet darkly hilarious story about the overwhelming weight of guilt and the blurriness of morality. The characters are complex and easy to connect with, the jokes all land, and the third act is easily one of the best in the subgenre.
In Bruges
Release Date February 8, 2008
Cast Elizabeth Berrington , Rudy Blomme , Olivier Bonjour , Mark Donovan , Ann Elsley , Colin Farrell
Runtime 107
2 ‘The Sting’ (1973)
Directed by George Roy Hill
Image via Universal Pictures
Winner of a whopping seven Oscars, including Best Picture, The Sting is about two grifters who team up to pull off the ultimate con in order to avenge the killing of an old friend at the hands of a powerful gangster. It was the film that saw the long-awaited reunion of director George Roy Hill and actors Paul Newman and Robert Redford (one of the most iconic actor duos in Hollywood history), four years after Butch Cassidy and the Sundance Kid.
One of the most exquisitely entertaining classics of the ’70s, The Sting’s sharp editing and clever script make its over-2-hour runtime flow like a charm. Charming and humorous, the movie proves that popcorn flicks can not only be genuinely great, but even have lots of artistic merit. Queen of heist comedies — and arguably of gangster comedies, too — The Sting is the kind of film that all movie fans should watch at least once in their lives.
The Sting
Release Date December 25, 1973
Director George Roy Hill
Runtime 129
1 ‘Some Like It Hot’ (1959)
Directed by Billy Wilder
Image via United Artists
It’s easy to throw around the phrase “this comedy was way ahead of its time,” but much harder to apply it to a movie that actually deserves it. Some Like It Hot is undeniably a comedy that was ahead of its time if there ever was one. In it, two male musicians have to flee the state after witnessing a mob hit. In order to successfully do so, they have to infiltrate an all-female band disguised as women.
One of the best romance crime movies of all time, Some Like It Hot had such overt depictions of sexuality, such bold explorations of themes of gender, and so much cross-dressing, that it didn’t receive the approval of the Production Code in 1959. Then again, Billy Wilder, one of the most influential directors in Hollywood history, was always one to push the envelope when it came to what could be depicted in films. The result here is an absolute gem. Some Like It Hot has endearing characters, hilarious performances, a sharp sense of humor, and one of the funniest endings of any comedy movie.
Some Like It Hot
Release Date March 19, 1959
Director Billy Wilder
Runtime 121 minutes
NEXT:The Best Gangster Movies, Ranked