The most amusing mob comedy movies possess a special talent for making us laugh at something that, in reality, isn’t particularly funny. Let’s be honest, the mob is notorious for their unlawful activities and brutality. So, discovering humor in such a dark subject is quite a challenge. However, the most uproarious mafia movies manage to accomplish just that. They either mock or imitate more serious gangster films, or they capitalize on the exaggerated personalities of mobster characters. Some of the most entertaining examples, like Analyze This, revolve around individuals who unexpectedly find themselves tangled up with the mafia.
On this list, you’ll encounter some well-known actors, including Robert De Niro, Dean Martin, and Michelle Pfeiffer. So, here’s an offer you can’t resist: check out the best mob comedy movies below. And if you believe there’s a top-notch mob comedy film that we overlooked, please add it so that other users can rate it too.
1. Married to the Mob
In this film, we follow the journey of a Mafia hitman’s wife who’s trying to escape the grip of organized crime after her husband is killed. Along the way, she meets this FBI guy who gets caught up in her mission to turn her life around and avoid the suffocating hold of the mob. Trust me, this story has got some interesting characters, a bit of romance, and even some funny moments, all while exploring the theme of finding oneself.
Released: 1988
Directed by: Jonathan Demme
Actors: Michelle Pfeiffer, Alec Baldwin, Lisa Kudrow
2. Mickey Blue Eyes
So there’s this shy British auctioneer who’s about to get hitched to a sweet schoolteacher. Only problem is, he needs to win over her Mafioso dad before they can say their “I dos.” And let me tell you, things take a wild turn when he gets mixed up in a bunch of hilarious mob shenanigans. With a cast that brings on the charm and impeccable comedic timing, this flick is a total gem in the genre.
Released: 1999
Directed by: Kelly Makin
Actors: Hugh Grant, James Caan, Jeanne Tripplehorn
3. Analyze This
Anxiety-ridden mafia boss needs therapy but finds a hesitant therapist. Soon enough, the therapist gets caught up in the chaos of the mobster’s world. As they navigate their unique relationship, they discover unexpected truths about one another, all while facing the comical challenges that arise from their vastly different lives. The film is a must-watch, thanks to its clever dialogue, incredible chemistry between the lead actors, and the perfect balance of tension and humor.
Released: 1999
Directed by: Harold Ramis
Actors: Robert De Niro, Billy Crystal, Lisa Kudrow
4. My Blue Heaven
So, there’s this dude who used to be involved with the mob, and now he’s in the witness protection program. His goal? Live a calm and peaceful life. But, of course, it’s never that easy. Enter an FBI agent, assigned to protect him from harm. But trouble seems to follow our guy like a magnet, and the agent gets dragged into a bunch of hilarious predicaments as they try to avoid the mob’s relentless pursuit to shut them up. Trust me, this movie has got it all – action, humor, and an engaging storyline that will have you laughing out loud.
Released: 1990
Directed by: Herbert Ross
Actors: Steve Martin, Rick Moranis, Joan Cusack
5. Some Like It Hot
So, there are these two musicians, right? And they’re having a tough time making it in the music industry. But then, by some crazy twist of fate, they happen to witness a mafia hit. Talk about being in the wrong place at the wrong time!
Now, these guys are faced with a serious predicament. They gotta find a way to escape the wrath of the mob. And you won’t believe what they come up with: they decide to dress up as women! Yeah, you heard that right. They figure that by disguising themselves, they might just be able to slip away unnoticed.
As luck would have it, they stumble upon an all-female band and decide to join. Can you imagine the hilarity that ensues? These dudes are trying their best to keep their true identities a secret, but let’s just say it doesn’t exactly go according to plan. We’re talking about a rollercoaster of comedic misadventures here!
The lead actors really shine in this one, delivering classic performances that will have you in stitches. And the dialogue? It’s sharp, witty, and will keep you engaged throughout. This movie is a true masterpiece of situational humor and disguise that has stood the test of time. Get ready to laugh your socks off!
Released: 1959
Directed by: Billy Wilder
Actors: Tony Curtis, Jack Lemmon, Marilyn Monroe
6. 8 Heads in a Duffel Bag
So, there’s this poor college student who ends up with a major mix-up involving his luggage. And guess what? It’s not just any mix-up. His bags get switched with those of a freakin’ hitman! Talk about bad luck, right?
Now, here’s where the chaos kicks in. Our hapless student finds himself in a full-blown frenzy to return eight severed heads. Yeah, you heard that right, EIGHT severed heads! And why is he in such a hurry? Well, he’s got to make sure a powerful mob boss doesn’t realize the mistake.
But wait, there’s more! As if things couldn’t get any crazier, our student and his buddies get caught up in a bunch of misunderstandings along the way. This puts their lives in danger, but hey, at least it generates non-stop laughs for us.
Now, here’s why you should watch this film. It’s got razor-sharp wit, top-notch performances, and a twisted sense of humor that’s all its own. So, if you’re up for a wild ride filled with dark hilarity, this is the movie for you.
Released: 1997
Directed by: Tom Schulman
Actors: Joe Pesci, Andy Comeau, Kristy Swanson
7. Midnight Run
In this film, a bounty hunter finds himself in the task of escorting a mob accountant across the country. It’s no easy feat, as they have to dodge not only the police but also the Mafia hot on their heels. But amidst the chaos, these two very different individuals form an unexpected bond. And let me tell you, their journey is filled with hilarious moments that will make you chuckle.
What sets this movie apart is its snappy dialogue, heart-pounding stunts, and perfectly timed humor. It’s a prime example of a chase comedy that will keep you entertained from start to finish.
Released: 1988
Directed by: Martin Brest
Actors: Robert De Niro, Charles Grodin, Yaphet Kotto
8. The Whole Nine Yards
In this film, we meet an anxious dentist who finds out that his new neighbor is actually a notorious hitman in hiding. Surprisingly, the dentist sees an opportunity here and decides to team up with the criminal. His motive? To finally get rid of his nagging wife. Together, they embark on a series of outrageous and hilarious adventures, where their reliance on each other becomes crucial for survival. With a talented cast and clever humor, this dark comedy promises an exciting and entertaining experience.
Released: 2000
Directed by: Jonathan Lynn
Actors: Bruce Willis, Matthew Perry, Rosanna Arquette
9. Analyze That
Picking up from where the first movie left off, this sequel delves into the ongoing relationship between the mob boss and his therapist. They have to navigate the challenges of life in prison as well as struggle with their own family issues. Despite their personal growth, they must confront the emotional consequences of their actions, all the while maintaining their witty banter and undeniable connection. This film effectively expands on its predecessor, delving into deeper themes while still delivering its trademark humor.
Released: 2002
Directed by: Harold Ramis
Actors: Robert De Niro, Billy Crystal, Lisa Kudrow
10. Johnny Dangerously
This film tells the story of an ordinary guy who gets caught up in the world of organized crime while trying to assist his family. As the plot unfolds, he ends up becoming a major mob leader. The movie is packed with hilarious moments and cleverly mocks the typical mobster story, adding a light-hearted touch to the genre. The outstanding performances and clever visual jokes make this comedy both wacky and nostalgic.
Released: 1984
Directed by: Amy Heckerling
Actors: Michael Keaton, Joe Piscopo, Marilu Henner
11. Oscar
A notorious gangster is determined to honor his dying father’s wish by leaving his criminal life behind and embracing respectability. However, this choice sets off a chain of hilarious mix-ups, cases of mistaken identity, and wild schemes that will have viewers laughing non-stop. Boasting a superb cast and lightning-fast humor, this movie takes audiences on a side-splitting adventure through the realm of personal transformation.
Released: 1991
Directed by: John Landis
Actors: Sylvester Stallone, Ornella Muti, Don Ameche