Many of the greatest gangster movies are violent and dark in tone. Think: Luca Brasi getting garroted inside Virgil “The Turk” Sollozzo’s lair in The Godfather, or Al Capone beating one of his Capos to death with a baseball bat at a banquet gathering in The Untouchables. Besides that, there tends to be plenty of betrayals, mistreatment, and sad outcomes for both likable and unlikable characters.
However, there are a few gangster flicks that don’t maintain a gloomy atmosphere from start to finish. In these films, the hoodlums mainly stand out because of their buffoonery rather than their ruthlessness. They keep finding themselves in the most awkward scenarios, and any attempts to get themselves out of their mess only result in funnier outcomes. In the ‘90s, such kinds of comedies were even more common and the following are the ones that stood out more.
Here are the 10 funniest gangster comedy movies of the 1990s.
10 8 Heads in a Duffel Bag (1997)
In 8 Heads in a Duffel Bag, mob boss Big Sep isn’t the kind to nod in satisfaction whenever his henchmen tell him they have successfully carried out a hit. He needs proof, so when he is informed that eight men of a rival gang have been killed, he demands to see the heads. Tommy Spinelli (Joe Pesci) is thus tasked with transporting the heads across the country to Big Sep, but an airport mix-up causes him and Charlie (a tourist heading for Mexico) to grab each other’s bags.
Why It’s Funny
Fresh out of starring in two of the greatest gangster movies of the ‘90s (Goodfellas and Casino), Pesci once again plays a Cosa Nostra member who is eager to impress his boss. Both he and Andy Comeu wonderfully channel their characters’ frantic mannerisms as they attempt to get back their respective luggage. More mayhem unfolds when one of the heads gets lost, resulting in a new “head replacement” arc that turns out to be a lot wilder.
The movie is also packed with several awkward exchanges that either involve Spinelli questioning and bullying people who might have an idea where the heads are, or Charlie trying to get people to help him get rid of the bag. Stream on Roku and Freevee
9 Oscar (1991)
Oscar isn't highly rated, but it’s one of Sylvester Stallone's better comedic efforts — better than Stop or My Mom Will Shoot, which the actor was tricked into starring in by Arnold Schwarzenegger. Here, Stallone plays Angelo "Snaps" Provolone, a mob boss who promises his dying father that he will quit crime. However, doing so proves harder than he expected.
Why It’s Funny
Stallone frequently seems like he is out of his depth here. He clearly would rather be holding a gun than cracking jokes, but he redeems himself several times in the film. Above all, Oscar shines because of the wordplay. “This is your third fiancé today, and it ain't even lunch yet!” Snaps tells his daughter in one scene, referring to her indecision regarding who to marry.
When it comes to the slapstick moments, director John Landis makes some clever references to classic films. For example, a scene where Stallone dangles dangerously from a giant public wall clock is inspired by a Harold Lloyd stunt from the Silent Era film, Safety Last. Rent on Prime Video
8 Analyze This (1999)
Analyze This drew several comparisons to The Sopranos when it premiered. Like the HBO drama, it revolves around a mob boss (Robert De Niro), who seeks the help of a psychiatrist after suffering various panic attacks. The film is even mentioned in the Season 2 premiere, "Guy Walks into a Psychiatrist's Office...".
Why It’s Funny
No one handles mafia roles better than De Niro, and the actor delivers once again here. Like Pesci, De Niro is also known to have a comedic bone inside him, so he handles most of the gags with ease. Besides that, the psychiatry sessions are arguably more entertaining than those in The Sopranos. For example, when De Niro’s character is asked why he has a comare (mistress), he claims it would be immoral for him to kiss the same mouth (his wife’s) that kisses his kids. Stream on DIRECTV
7 Dick Tracy (1990)
Dick Tracy
- Release Date
- April 5, 1990
- Cast
- Warren Beatty , Charlie Korsmo , Michael Donovan O'Donnell , Jim Wilkey , Stig Eldred , Neil Summers
- Rating
- PG
- Runtime
- 105
Based on the 1930s comic strip of the same name, Dick Tracy follows the titular detective (Warren Beatty) as he digs up evidence to help him nail the city’s top mob boss, Alphonse "Big Boy" Caprice. He hopes the barroom singer Mahoney (Madonna), will help him join the dots, but that becomes hard because she is keener on developing a romantic relationship with him.
Why It’s Funny
All the mobsters have hilarious names that match their attributes. For example, Caprice’s henchman — who speaks in a Sicilian accent and embodies the “Mumbling Brando” gangster movie trope — is simply called Mumbles. Interestingly, he can easily switch to coherent English if he is in a tricky situation. Caprice’s assistant, on the other hand, is called Numbers, while a piano player at a popular nightclub is called 88 Keys. In addition to that, the mannerisms are all the over-the-top kind. One gangster is so good with a submachine gun that he can write words on walls using bullets. Rent on AppleTV
6 Mickey Blue Eyes (1999)
In Mickey Blue Eyes, young English auctioneer Michael Felgate (Hugh Grant) gets devastated when his girlfriend rejects his marriage proposal. He soon learns that she did it because her father is a mob boss, and she doesn’t want him to get caught up in the family business. Undeterred, Mickey keeps pursuing her, a decision that leads him into a deadly alliance with her father. Nine of the movie’s cast members went on to appear in The Sopranos.
Why It’s Funny
Cosa Nostra buffs will easily catch the numerous hilarious references to other gangster flicks. When Michael’s potential father-in-law is teaching him how to behave like a mobster, he reminds him of the importance of switching the letter "T" for the letter "D." Still, he has a hard time getting him to pronounce “fuggeddaboutit,” a word frequently used by Al Pacino’s character in Donnie Brasco.
In a later scene, a waitress even tells him that he talks funny. In order to learn how to impress the man, Michael quietly tells himself, “Note to self... rent Goodfellas, Casino, Godfather 1, 2, 3.” Rent on AppleTV
5 Mafia! (1998)
Mafia! directly spoofs Martin Scorsese’s gangster flicks, though it also parodies scenes from The Godfather and movies like The English Patient and Forrest Gump. In it, a Korean War veteran emerges as the clear favorite to take over his dying father’s Cosa Nostra empire. Unfortunately, various disagreements and rivalries develop, making the transition process a lot harder.
Why It’s Funny
The film proudly embraces its fatuousness, hence there are plenty of scenes that remain engraved on the viewers' mind. One standout moment involves the aging Don getting shot by assassins. As he staggers around seeking help, people think he is doing a street dance, so they join in. When the assassins shoot him some more, he appears to be executing different dance styles, so everyone copies him.
In another silly scene, he makes a “falling star wish” for his wife’s breasts to expand and they do so without her noticing. The same matriarch develops a reputation for farting loudly in public. Rent on AppleTV
4 Get Shorty (1995)
Get Shorty
- Release Date
- October 20, 1995
- Rating
- R
- Runtime
- 105
Get Shorty is based on Elmore Leonard’s novel of the same name, and in it, loan shark Chili Palmer (John Travolta) is tasked by a local mob boss to collect a debt from a Hollywood horror movie producer. When Chilli meets the lead actress in one of the producer’s movies, a romance develops, but his decision to pair up with her comes with a new set of complications.
Why It’s Funny
Plenty of Elmore Leonard books were adapted in the ‘90s, but Get Shorty remains the most recommendable one for anyone looking for laughs. Every actor performs to their potential, but Travolta still owns the movie, thanks to his expert execution of some of the comedic moments. Whether he is grabbing James Gandolfini and throwing him down a staircase or throwing pickup lines, there is no single minute that he wastes. Stream on Max
3 The Freshman (1990)
The Freshman has one of the greatest con artists in movie history and that’s none other than Carmine Sabatini (Marlon Brando). Interestingly, he dresses exactly like Brando’s Godfather character Vito Corleone. Because he is an influential local crime boss, he convinces everyone that Vito Corleone is based on him.
Through this lie, he is able to gain trust and respect, especially when he starts a restaurant that allegedly sells the meat of endangered animals. His clients are the corrupt kind, so he forces them to pay large sums to dine in his establishment, only for it to later turn out that it was normal meat all along.
Why It’s Funny
Sabatini is hardly the funniest character. Credit goes to the tons of aberrant supporting characters, who, for some reason, cannot behave normally. Most of them have nothing to do with mob life, but they somehow get caught up in it. Things get even more interesting when a college student is tasked with picking up a Komodo Dragon from an airport and delivering it to a certain address. As expected, it breaks free at some point, resulting in a brilliant chase sequence. Stream on Paramount+
2 My Blue Heaven (1990)
My Blue Heaven is an unofficial Goodfellas sequel. Both movies are based on the life of mobster Henry Hill, but the former covers his life after he went into witness protection. While hiding in a small suburb in California, the former gangster becomes a problem for Barney Coopersmith (the FBI agent tasked with watching him) because of his inability to adhere to the rules.
Why It’s Funny
The film’s humor stems from watching the mobster struggling to adjust to life in a sleepy suburban area. He keeps cursing and making attempts to get out of his situation, only to fail miserably. My Blue Heaven also leans heavily on Cosa Nostra stereotypes; for instance, the character’s accent is extremely exaggerated. Furthermore, he has a single-minded perspective on life. To him, it’s either the mob way or no way at all. Rent on AppleTV
1 The Godson (1998)
The Godson is yet another parody of The Godfather that is full of endless laughs. In it, Giuseppe "The Guppy" Calzone (Kevin McDonald) takes over the Calzone crime family after his brother’s death. His aging father is not convinced about his toughness, so he sends him to a mob school. While he is away, a rival Don takes it as an opportunity to strike.
Why It’s Funny
Director Bob Hoge wastes no time in pumping up the film’s ridiculousness. In the opening scenes, Giuseppe’s brother survives several incidents that ought to have killed him — including assassins firing at him and his car getting blown up — only for him to die after tripping over his hanging shoelaces and knocking his temple on a fire hydrant.
The humor isn’t limited to the proceedings either. There are hilarious fourth wall-breaking moments and unexpected credit gags. “No one was harmed during the making of this movie...but we blew the sh** out of that cab, " a line reads at the end. Another scene involves the protagonist begging the audience to buy the movie’s merchandise so that he can avoid bankruptcy. Stream on Roku
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