The 10 Most Cringeworthy Movies of All Time, Ranked
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The word “cringeworthy” can be an insult when applied to something that’s not trying to be cringeworthy. It’s especially brutal to call something that when you can tell that thing is trying to be cool, but when, say, a movie is trying to be cringeworthy, and it does indeed feel cringeworthy, then it’s successful. And if you’ve watched your fair share of comedies over the years, you'll know that a few do navigate cringe-inducing territory to mine laughs.
Below are some of the most cringeworthy movies of all time, and some are indeed comedies, while others blend comedy with some other more intense genres, and then one is being included while not at all being a comedy. Basically, these films are all great, but they're also quite challenging in various ways, and maybe not the sorts of movies you can casually pop up on at any random time.
10 'There's Something About Mary' (1998)
An easier watch than most movies here, There’s Something About Mary is a broad and largely enjoyable comedy, and maybe the kind you could call a rom-com if you wanted to, but there’s more comedy than romance here. And like, there’s minimal heart because there’s some romance, but then you take into account how crude some of the comedy is, and it feels fair to say that’s what the movie’s really focused on doing.
It scores a place here largely because of what happens during a prom night scene early on, and then also for a certain scene that involves something which gets mistaken for hair gel. There’s Something About Mary is a largely approachable cringe comedy done right (again, for the most part), and it’s a good time, even with all the wince-inducing parts.
9 'Wild Tales' (2014)
One of the best anthology movies perhaps even of all time, Wild Tales is about half a dozen different stories that each focus on a different character or set of characters, though most of them are about revenge in one way or another. Also, each one investigates some kind of social situation or disagreement that spirals out of control in incredibly heightened ways, to the point where it functions as a dark comedy, for the most part.
It’s also a thriller, and definitely one of the more suspenseful dark comedies out there, showing that you can very much be biting your nails while laughing at something at the same time, and have it work. The tales are wild, and they're all engaging, too, with Wild Tales avoiding that unfortunately common issue of inconsistency that plagues a great many less impressive anthology films.
8 'Brazil' (1985)
Brazil bravely attempts to be both a dystopian movie and surreal comedy at the same time, and kind of makes it work. Like, it is an exhausting film just because of how much it throws at you, but it’s fitting when the events of the film also throw so much at the hapless protagonist, because he lives in a mad world and he seems like he has especially bad luck within that said mad world.
You get an idea of where it’s probably headed early on, and then much of Brazil feels like watching a car collide with that inevitable thing, so to speak. And you're watching for a while, if you're tackling the “proper” version of Brazil, since it’s almost 2.5 hours long all up. Absolute nightmare of a movie, but in a good way.
7 'Krisha' (2015)
Krisha is the only movie here that you're not going to find any source anywhere describing as either a comedy or a part-comedy. This is a full-on family drama, and it takes place during Thanksgiving one year that sees the titular character trying to reintegrate with members of her family after a period of estrangement, but ongoing tensions and personal demons make the pursuit of such a thing increasingly hopeless.
Once again, the word “cringeworthy” is not being used in a bad way here, and it does feel a bit strange calling Krisha that because of what that word sometimes means, but the discomfort here is intense and feels especially real. The authenticity of Krisha can be admired while also being cursed, since the way all this is executed makes the film a very tough watch. It does have to be, to some extent, but there are ways the knife is twisted, so to speak, that are hard to see coming, even if you think you're somewhat prepared for something heavy.
6 'Borat' (2006)
There are different reasons to find Borat offensive or boundary-pushing, and then also a lot that can be taken from the film comedically, in the sense that people find simple things funny here while others dig a bit deeper and appreciate the satire. Or you can do a bit of both, with the contrast between lowbrow humor and some weightier stuff being commented on making things interesting.
Also, Borat is a mockumentary, famously so, but the kind where not everyone seemed in on the joke, which separates it from something like This Is Spinal Tap. That sense of danger and the whole deceitful nature of the film adds a lot to the discomfort one’s inevitably going to feel while watching it, but at least chaos is caused – and dicey topics are tackled – for a good reason here.
5 'Shiva Baby' (2020)
Almost the entirety of Shiva Baby takes place within a confined location, being a shiva at a house, done for people to mourn. But the main character has a lot going on besides grief, and so do all the other mourners, and so the gathering ends up being an intense and uncomfortable one on a bunch of different levels, with different secrets being kept from different people.
It’s almost like a farce, the way things escalate, but Shiva Baby also comes close to feeling like a strange sort of thriller just because of how bad things get, and the surprisingly large amount of suspense that gets drawn from it all. It’s really impressive how much is done – and how much you're made to feel, even if some of those feelings are very unpleasant – within a short runtime and with what appeared to be a pretty limited budget.
4 'Happiness' (1998)
It might be easiest to say that Happiness is a movie about things that other movies don’t really want to be about. An assortment of taboo subjects get tackled here, and there’s this blunt acknowledgment that these things happen, that people do them, and that that’s the world everyone has to live in. You might be aware of that to some extent, sure, but having to confront it – even within a fictional film – is another matter.
All the while, Happiness is also a comedy, just an extremely dark one, and really, calling it cringeworthy is quite the understatement when it chooses to tackle what it does. It’s hard to even describe what the movie’s about, because the words, even choosing plain language, might well be too much. Tread carefully, and expect a lot of sadness, even with the comedy being there and the title also being what it is.
3 'Friendship' (2024)
Before things fall apart, Friendship is probably best described as a quirky comedy, since it’s about two middle-aged men who find themselves bonding, even though they don’t seem to have a lot in common. One is introduced to the other’s larger friend group, and that’s where a mess is made, because a couple of very awkward occurrences end the friendship between the two men, and the rejected one reacts quite poorly, to say the least.
So, it’s awkward when things get, you know, awkward, and then Friendship keeps escalating the messiness of the situation, and things get worse and worse for both men. It definitely doesn’t feel quirky by the end, unless you're talking about the very, very last note of the film, but it does stay pretty funny throughout, certainly feeling like one of the more distinctive feature-length comedies in recent memory.
2 'The King of Comedy' (1982)
There are other Martin Scorsese movies that are more intense in the traditional sense than The King of Comedy, but still, this one is uniquely uncomfortable and cringe-inducing. That’s by design, like all the movies here, with The King of Comedy being a look at one man going way too far in the pursuit of fame, because part of his plan to get attention involves stalking and then kidnapping a comedian he admires.
It’s a great movie, though, for what it’s worth, and very much ahead of its time regarding what it says and how it says it all.
That also makes The King of Comedy a bit of a thriller, and sure, there is some intentional humor here, but the funniest joke is probably the title having the word “Comedy” while there really isn't a ton of actual fun comedy. It’s the kind you wince at, and maybe you laugh because you feel unnerved by it all. It’s a great movie, though, for what it’s worth, and very much ahead of its time regarding what it says and how it says it all… just a tough watch, in some regards.
1 'Windy City Heat' (2003)
You can connect Windy City Heat to The King of Comedy in the sense that it’s also about a man who’s desperate to be famous, but he wants to be an actor rather than a comedian. And then the other big difference is that Windy City Heat is a documentary, or a perfectly-staged mockumentary, which makes everything more cringeworthy, since it feels especially real, and it’s honestly a lot to handle.
Like, Windy City Heat is very much not for everyone. Perry Caravello is like a real-life Ignatius J. Reilly, so he’s not particularly endearing, but he does suffer immensely, being the subject of this feature-length prank done to trick him into thinking he was starring in a real movie. Since he’s not very endearing, that does make it kind of funny, because those pranking him aren’t good people, but neither is he. There’s honestly a fair bit to grapple with here, at least emotionally, if you want to dig in beyond the broad and ridiculous comedy on offer.
Windy City Heat
- Release Date
- October 12, 2003
- Runtime
- 92 minutes
- Director
- Bobcat Goldthwait
- Writers
- Don Barris
Cast
-
Don Barris
Self / Big Lou
-
Perry Caravello
Self / Stone Fury
-
Tony Barbieri
Mole / Brock / John Quincy Adams
-
Bobcat Goldthwait
The Director
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