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Gangster movies are often dramas, because the stories told are, well, dramatic. Back during the Golden Age of Hollywood, when the gangster genre was first being fleshed out and made a thing, the stories were almost always of the rise-and-fall variety, with someone becoming a criminal, getting powerful, and then being brought down, because crime just couldn’t pay, in the long run; it’s not the message anyone wanted to put across.
Eventually, things got a little more complicated, not necessarily because of The Godfather, but that one is indicative of a new era of sorts for the gangster genre. And The Godfather, while more morally complex, is also pretty dramatic and not exactly a laugh riot. Thankfully, if you are after gangster movies that are funny, the ones below might satisfy, some of them being broad and quite silly, while others are probably more definable as crime-related dramedies.
10
‘Prizzi’s Honor’ (1985)
Sure, Jack Nicholson was Oscar-nominated for better movies than Prizzi’s Honor, but this one does still have the honor of housing an Oscar-nominated Nicholson performance (being one of 12… kind of crazy that The Shining isn’t one, but oh well). He plays a hitman in Prizzi’s Honor who works for a dangerous and powerful crime family, and finds his life taking a turn when he happens to fall in love with a woman who’s also an assassin.
That is the premise, and you sort of just have to roll with it, even if it might sound, on the surface, a little too heightened, even for a crime/gangster movie with a comedic tone. Still, Prizzi’s Honor shows Jack Nicholson can do just about anything as an actor, since he’s pretty good in this film, and so too is Anjelica Huston (being directed by her father, John Huston, in what ended up being his penultimate film), who won Best Supporting Actress for her role here.
9
‘The Freshman’ (1990)
There were many crime movies that came out in 1990, perhaps more high-profile ones than usual, including The Godfather Part III (definitely not a comedy), and a couple more that’ll be mentioned in a bit. But it’s worth bringing up The Godfather, since The Freshman works as a parody of sorts to that first film, since that one starred Marlon Brando and he’s in The Freshman as an older gangster who’s kind of similar, in some ways, to Vito Corleone.
Matthew Broderick’s character certainly thinks so, as he’s a film student who ends up getting mixed up with the mob, and comedic hijinks ensue. Or they’re supposed to ensue. The Freshman is, unfortunately, a little inconsistent, and maybe one-note with the main joke it tells again and again throughout, yet it’s kind of neat and clever at times. Certainly not awful, though, and arguably a tad overlooked.
8
‘Guys and Dolls’ (1955)
Another Marlon Brando movie, but this time one from before he did The Godfather, here’s Guys and Dolls, which is – strange as it might sound – a comedy/romance/crime/musical movie, all at once (and not particularly intense, the way some crime-musical hybrids are). It’s a lot, and it’s kind of big (even borderline epic) in the way quite a few musicals from around the middle of the 20th century liked to be, with a perhaps overlong runtime here of almost 2.5 hours.
There’s fun to be had with the excessiveness of it all, though, and getting to see Brando and Frank Sinatra share the screen is probably worth the price of admission if you like Golden Age of Hollywood musicals. It’s about some people affiliated with some criminals and also their love lives, and some other stuff. They just pile a lot into Guys and Dolls, hoping you, the viewer, will think enough of it works.
7
‘Snatch’ (2000)
The first Guy Ritchie movie worth mentioning, for present purposes, Snatch is quite a lot, and maybe too much, all of it crammed into a shorter runtime than the (also overstuffed) aforementioned Guys and Dolls. There are so many different characters here, all of them intersecting in different ways, with those clashes fluctuating between being funny at times and kind of intense at other points.
But chaos, here, does feel like the point, and Snatch does a great job at taking you along for a relentless ride that it pretty much doesn’t expect you’ll keep up with, 100%. And that’s mostly okay when things are as entertaining as this film manages to be, at certain points. There’s one other gangster movie Ritchie directed that is a little stronger overall than Snatch, but more on that one in a bit.
6
‘Analyze This’ (1999)
The elephant in the room, when it comes to Analyze This, is the fact that it has the same set-up, narratively speaking, as The Sopranos. And no, it’s not as good as The Sopranos, but what is? It’s still good, and also, it’s not as easy as saying that Analyze This is like a comedic take on the whole idea of “What if a gangster went to therapy?,” since The Sopranos pretty much was a dark comedy a lot of the time.
Analyze This commits to its simple premise well, and finds quite a bit of comedic material to mine throughout.
Robert De Niro gets to put a broadly comedic spin on the sorts of characters he’s well-known for playing, a little like Brando in the aforementioned The Freshman, with De Niro also being paired well here with Billy Crystal, who is, of course, best known for starring in comedies. Analyze This commits to its simple premise well, and finds quite a bit of comedic material to mine throughout, making it a pretty fun watch, overall.
5
‘Dick Tracy’ (1990)
It’s hard to describe Dick Tracy to someone if they haven’t seen it, because it’s pretty gonzo, all by design. It’s also a comic book movie, or maybe, more accurately, a comic strip movie, since Dick Tracy originated as a newspaper comic. The movie goes all out in replicating the feel of old-school comics, with it being broad, oftentimes goofy, and certainly over-the-top.
And stylized. Dick Tracy, though flawed and more than a little messy, does look visually bold – and overall pretty great – throughout. It’s also hard to overlook the immense cast here, with Warren Beatty (also the director), Madonna, and Al Pacino starring in the film, and the supporting cast including too many people to name them all, but the likes of Dustin Hoffman, Catherine O’Hara, James Caan, Paul Sorvino, Mandy Patinkin, and Dick Van Dyke, just for starters.
4
‘Goodfellas’ (1990)
Of all the movies here, Goodfellas is probably the best, and it’s also perhaps the least definable as a comedy. It’s not the funniest, but it’s generally not concerned with being an outright comedy, or even a partial comedy, and the humor here is pretty grounded and natural, as a result. It’s part of the way of life depicted, and it’s the movie saying, “Hey, when people in the mafia aren’t shooting each other or threatening other people, they like to joke around quite a bit.”
What you have, then, is a movie that’s surprisingly funny at times, and it’s not just here because the whole “Funny how?” sequence is so iconic, but that part of the film does help. Goodfellas tackles a lot of ground emotionally, with some of the film being pretty intense and downbeat, while certain sequences (and even just some smaller moments here and there) prove honestly quite funny.
3
‘Lock, Stock and Two Smoking Barrels’ (1998)
Guy Ritchie’s first movie, Lock, Stock and Two Smoking Barrels, still feels like it could well be his very best. Like Snatch, it’s a chaotic and comedic gangster movie of sorts, following a group of fairly small-scale criminals who need money fast, so they try to execute a heist that gains them attention from people they probably don’t want to attract (gangsters, basically, and some of them a bit more than small-scale).
It’s a bit of a farce, ultimately, with one bad decision setting off a chain of dominoes, and watching everything fall down proves comedic over anything else. Lock, Stock and Two Smoking Barrels is a dark comedy, sure, but it’s hard to feel too bad about laughing when everyone is either quite flawed or incredibly flawed. It gets the balance right, and it’s ultimately complex and chaotic in a very satisfying way.
2
‘In Bruges’ (2008)
Potentially the best of all the British gangster comedies, In Bruges is, admittedly, not really a gangster movie at the start of its runtime. It’s about two hitmen who are given an unconventional task that involves waiting around in Bruges, Belgium, a place one of them intensely dislikes, so they talk and bicker a lot, until it becomes clear why they’re there.
It takes a while to reveal that, so even if the film’s old, it still feels wrong to go into too much. In Bruges ends up being surprising, and there is an eventual gangster element (well, a character who’s a gangster) playing a part, so it counts enough to be here. It’s very funny, is the main thing, even if all the comedy is paired with an almost equal amount of emotionally intense stuff.
1
‘Pulp Fiction’ (1994)
You can push back on Pulp Fiction being a true gangster movie if you want, but things were broadened enough before to allow Goodfellas into a ranking about comedies, even though it wasn’t a full-on comedy, so Pulp Fiction being kind of a gangster movie is enough. Marsellus Wallace is a pretty fearsome gangster, and he doesn’t have the most screen time, but he is the character around whom all the stories in Pulp Fiction revolve.
There’s a boxer who wrongs him, a pair of hitmen who carry out a chaotic mission for him, and then one of those hitmen also takes Marsellus Wallace’s wife, Mia, out on (another chaotic) night, so everyone’s affiliated with a gangster, more or less. Anyway, Pulp Fiction is intense and even a little horrifying at times, but there’s a lot of dark comedy and very memorable quotes throughout, with it being probably Quentin Tarantino’s best film overall (and his funniest, too).
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Jeremy Urquhart
Almontather Rassoul
