{"id":927548,"date":"2026-10-10T08:18:16","date_gmt":"2026-10-10T08:18:16","guid":{"rendered":"https:\/\/www.newsbeep.com\/ca\/927548\/"},"modified":"2026-10-10T08:18:16","modified_gmt":"2026-10-10T08:18:16","slug":"the-10-most-cringeworthy-movies-of-all-time-ranked","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/ca\/927548\/","title":{"rendered":"The 10 Most Cringeworthy Movies of All Time, Ranked"},"content":{"rendered":"

The word \u201ccringeworthy\u201d can be an insult when applied to something that\u2019s not trying to be cringeworthy. It\u2019s 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\u2019s successful. And if you\u2019ve watched your fair share of comedies over the years, you’ll know that a few do navigate cringe-inducing territory to mine laughs.<\/p>\n

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.<\/p>\n

10 <\/p>\n

‘There’s Something About Mary’ (1998)<\/p>\n

\"Cameron
\n Cameron Diaz and Ben Stiller in There’s Something About MaryImage via 20th Century Fox<\/p>\n

An easier watch than most movies here, There\u2019s Something About Mary<\/a> is a broad and largely enjoyable comedy, and maybe the kind you could call a rom-com if you wanted to, but there\u2019s more comedy than romance here. And like, there\u2019s minimal heart because there\u2019s some romance, but then you take into account how crude some of the comedy is, and it feels fair to say that\u2019s what the movie\u2019s really focused on doing.<\/p>\n

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\u2019s Something About Mary is a largely approachable cringe comedy done right (again, for the most part), and it\u2019s a good time, even with all the wince-inducing parts<\/a>.<\/p>\n

9 <\/p>\n

‘Wild Tales’ (2014)<\/p>\n

\"\u00c9rica
\n \u00c9rica Rivas as the bride Romina in Wild TalesImage via Warner Bros.<\/p>\n

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.<\/p>\n

It\u2019s also a thriller, and definitely one of the more suspenseful dark comedies out there<\/a>, 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.<\/p>\n

8 <\/p>\n

‘Brazil’ (1985)<\/p>\n

\"Jonathan
\n Jonathan Pryce standing in a long hallway holding a present and a piece of paper in Brazil.Image via\u00a0Universal Pictures<\/p>\n

Brazil<\/a> 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\u2019s 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.<\/p>\n

You get an idea of where it\u2019s probably headed early on, and then much of Brazil feels like watching a car collide with that inevitable thing<\/a>, so to speak. And you’re watching for a while, if you’re tackling the \u201cproper\u201d version of Brazil, since it\u2019s almost 2.5 hours long all up. Absolute nightmare of a movie, but in a good way.<\/p>\n

7 <\/p>\n

‘Krisha’ (2015)<\/p>\n

\"Krisha
\n Krisha Fairchild in KrishaImage via A24<\/p>\n

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<\/a>, 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.<\/p>\n

Once again, the word \u201ccringeworthy\u201d 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.<\/p>\n

6 <\/p>\n

‘Borat’ (2006)<\/p>\n

\"Sacha
\n Sacha Baron Cohen at the rodeo in Borat (2006).Image via 20th Century Studios<\/p>\n

There are different reasons to find Borat offensive or boundary-pushing<\/a>, 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.<\/p>\n

Also, Borat<\/a> 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<\/a>. That sense of danger and the whole deceitful nature of the film adds a lot to the discomfort one\u2019s inevitably going to feel while watching it, but at least chaos is caused \u2013 and dicey topics are tackled \u2013 for a good reason here.<\/p>\n

5 <\/p>\n

‘Shiva Baby’ (2020)<\/p>\n

\"Danielle
\n Danielle (Rachel Sennott) listens to her mom, Debbie (Polly Draper) talk about her in Shiva Baby (2020)Image via Utopia<\/p>\n

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.<\/p>\n

It\u2019s 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<\/a> that gets drawn from it all. It\u2019s really impressive how much is done \u2013 and how much you’re made to feel, even if some of those feelings are very unpleasant \u2013 within a short runtime and with what appeared to be a pretty limited budget.<\/p>\n

4 <\/p>\n

‘Happiness’ (1998)<\/p>\n

\"Happiness
\n Image via\u00a0Good Machine Releasing<\/p>\n

It might be easiest to say that Happiness is a movie about things that other movies don\u2019t really want to be about. An assortment of taboo subjects get tackled here, and there\u2019s this blunt acknowledgment that these things happen, that people do them, and that that\u2019s the world everyone has to live in. You might be aware of that to some extent, sure, but having to confront it \u2013 even within a fictional film \u2013 is another matter.<\/p>\n

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\u2019s hard to even describe what the movie\u2019s about, because the words, even choosing plain language, might well be too much<\/a>. Tread carefully, and expect a lot of sadness, even with the comedy being there and the title also being what it is.<\/p>\n

3 <\/p>\n

‘Friendship’ (2024)<\/p>\n

Before things fall apart, Friendship<\/a> is probably best described as a quirky comedy, since it\u2019s about two middle-aged men who find themselves bonding, even though they don\u2019t seem to have a lot in common. One is introduced to the other\u2019s larger friend group, and that\u2019s 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.<\/p>\n

So, it\u2019s 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\u2019t feel quirky by the end, unless you’re talking about the very, very last note of the film<\/a>, but it does stay pretty funny throughout, certainly feeling like one of the more distinctive feature-length comedies in recent memory.<\/p>\n

2 <\/p>\n

‘The King of Comedy’ (1982)<\/p>\n

\"Rupert
\n Image via 20th Century Studios<\/p>\n

There are other Martin Scorsese movies<\/a> that are more intense in the traditional sense than The King of Comedy, but still, this one is uniquely uncomfortable and cringe-inducing. That\u2019s 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<\/a> he admires.<\/p>\n

It\u2019s a great movie, though, for what it\u2019s worth, and very much ahead of its time regarding what it says and how it says it all.<\/p>\n

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 \u201cComedy\u201d while there really isn’t a ton of actual fun comedy. It\u2019s the kind you wince at, and maybe you laugh because you feel unnerved by it all. It\u2019s a great movie, though, for what it\u2019s worth, and very much ahead of its time regarding what it says and how it says it all\u2026 just a tough watch, in some regards.<\/p>\n

1 <\/p>\n

‘Windy City Heat’ (2003)<\/p>\n

\"Windy
\n Perry Caravello as the star of Windy City Heat (2003)Image via\u00a0Comedy Central<\/p>\n

You can connect Windy City Heat<\/a> to The King of Comedy in the sense that it\u2019s also about a man who\u2019s 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\u2019s honestly a lot to handle.<\/p>\n

Like, Windy City Heat is very much not for everyone. Perry Caravello is like a real-life Ignatius J. Reilly<\/a>, so he\u2019s 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\u2019s not very endearing, that does make it kind of funny, because those pranking him aren\u2019t good people<\/a>, but neither is he. There\u2019s 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.<\/p>\n

\t\t\t\t\t\tWindy City Heat<\/p>\n

Release Date<\/p>\n

\t\t\t\t\t\t\t\t\tOctober 12, 2003<\/p>\n

Runtime<\/p>\n

\t\t\t\t92 minutes<\/p>\n

Director<\/p>\n

\t\t\t\t\t\t\t\t\t\t\t\t\t\t\tBobcat Goldthwait<\/p>\n

Writers<\/p>\n

\t\t\t\t\t\t\t\t\t\t\t\t\t\t\tDon Barris<\/p>\n

\n Cast\n <\/p>\n

\"Cast<\/p>\n

Don Barris<\/p>\n

\n Self \/ Big Lou\n <\/p>\n

\"Cast<\/p>\n

Perry Caravello<\/p>\n

\n Self \/ Stone Fury\n <\/p>\n

\"Cast<\/p>\n

Tony Barbieri<\/p>\n

\n Mole \/ Brock \/ John Quincy Adams\n <\/p>\n

\"instar49556481.jpg\"<\/p>\n

Bobcat Goldthwait<\/p>\n

\n The Director\n <\/p>\n","protected":false},"excerpt":{"rendered":"The word \u201ccringeworthy\u201d can be an insult when applied to something that\u2019s not trying to be cringeworthy. It\u2019s…\n","protected":false},"author":2,"featured_media":927549,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[27],"tags":[49,48,75,337],"class_list":["post-927548","post","type-post","status-publish","format-standard","has-post-thumbnail","category-movies","tag-ca","tag-canada","tag-entertainment","tag-movies"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts\/927548","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/comments?post=927548"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts\/927548\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/media\/927549"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/media?parent=927548"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/categories?post=927548"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/tags?post=927548"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}