Humor and awkwardness can be a comedic match made in heaven. Welcome to WatchMojo, and today we’re counting down our picks for the cringiest, most awkward comedies that’ll have you watching through your fingers. That means we’re looking at movies featuring awkward situations, as opposed to movies so bad they’ll make you cringe.
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00:00and you're asking me to do something that's impossible it's impossible don't you understand
00:05what what are you doing down there so late welcome to watch mojo and today we're counting down our
00:13picks for the cringiest most awkward comedies that i have you watching through your fingers
00:18that means we're looking at movies featuring awkward situations as opposed to movies so bad
00:24they'll make you cringe what a story mark number 10 american pie what exactly does third base feel
00:33like you want to take this one like warm apple pie for obvious reasons this won't be the last
00:44high school movie on this list we can't imagine more awkward fertile ground to start ourselves on
00:49do we really need to say more than four dorky high schoolers attempt with varying degrees of
00:55success to lose their virginity before the end of the school year hey nadia hi james ready to study
01:01oh he's always ready to study he's a real bookworm this kid dad i mean he's not not one of those
01:06nerdy guys but dad paul and chris weitz's uber raunchy comedy covers every time honored teen
01:12movie trope you would expect it to and still manages to throw its audience some nerve-wracking
01:17curveballs along the way an unexpected smash hit at the time of its release american pie broke new
01:24ground in painfully relatable cringe comedy and uh baking sort of well we'll just tell your mother
01:31that uh that we ate it all number nine death at a funeral i never realized dad was so popular um
01:39in fact i see it seems like he's got more friends now that he's dead than when he was alive
01:43director frank oz's lethally funny dark comedy serves to remind us that we shouldn't take each
01:48other for granted it is also a reminder of why you shouldn't pop mysterious pills at your fiance's
01:53uncle's funeral simon was there a dog in here just now what i'm sure there was a dog in here
02:03or do anything to arouse the ire of that same uncle's secret lover assembling an all-star cast
02:10uncle's secret lover assembling an all-star cast that includes matthew mcfadyen ewan brimner peter
02:16dinklage and alan tudyk eyes deftly maneuvers potential jarring tonal shifts to great effect
02:22above all the film setting lends itself beautifully to generating cringeworthy
02:26cinema is there any worse place for a drama to erupt
02:30what the hell are you doing in my dad's coffin number eight force majeure
02:55clearly north america doesn't have a monopoly on awkwardness
02:58while vacationing at a ski resort married couple tomas and ebba are forced to confront
03:03the cracks in their family after a false brush with death force majeure examines modern day
03:09infidelity parenthood and the toll of secrets we keep from each other the whole deliciously
03:14tense story illustrates swedish writer director ruben ushlon greatest strength the use of comedy
03:20to reveal profound truths about human nature he got so scared that he ran away from the table
03:33his 2022 film triangle of sadness builds on this using a more extreme approach to explore themes
03:40of class warfare and elitism his efforts were rewarded with an academy award nomination for
03:45best director and best original screenplay never argue with an idiot they'll only bring
03:50you down to their level and beat you with experience mark twain number seven meet the
03:57parents i i had no idea you could milk a cat oh yeah you can milk anything with nipples
04:06i have nipples greg could you milk me by now it's probably clear that awkward comedies are
04:12most effective when they're based on mundane everyday situations and meet the parents goes
04:17a long way improving that attempted to make a good impression on his girlfriend's uptight parents
04:22before he proposes a neurotic nurse played by ben stiller quickly finds himself teetering
04:28on the edge of the circle of trust it was a little rare for my taste but i but i was kidding i'm just
04:35okay relax relax the needles are jumping did we mention that his potential father-in-law
04:44robert de niro as the poster boy for being stern is ex-cia no pressure at all while the film's
04:51circumstances are excruciating by default the real fun for the viewer is in watching stiller
04:56and de niro push each other's buttons did you flush this toilet maybe you know what maybe
05:03jinx flushed it i saw a little jinx he come in last night um and he took a little squat it
05:08relieved himself number six super bad wait you changed your name to mclovin mclovin
05:19what kind of a stupid name is that fogel what are you trying to be an irish r&b singer
05:22seth rogan and evan goldberg mine their own high school experiences in writing super bad
05:28and their embarrassment is our game like the american pie gang before them jonah hill and
05:32michael cera plays teens looking to close out their senior year with a bang literally what
05:38begins as a coming-of-age tale spirals into a night-long odyssey involving a less-than-convincing
05:44fake id numskull cops and an impromptu musical performance the hurtings on me
05:51talk about the hurt and i will never be right no no no you gave a promise to me
06:00above all super bad never loses sight of the film's heart the bromance between hill and
06:05sarah's characters director greg mottola's timeless comedy reminds us as viewers that
06:11nothing compares to rooting for the underdog especially if the underdog in question brings
06:16to mind memories we'd rather forget hey greg why don't you go piss your pants again
06:20that was like eight years ago people don't forget number five the king of comedy jerry
06:27jerry let me show you a picture of my pride and joy
06:33that's good that's good yeah it is that's good hey jerry take it we've probably all fantasized
06:39about laughing it up on a talk show host's couch robert de niro's unstable clout chasing
06:44rupert pumpkin takes things a step further to pursue his dream of being a famous comedian
06:49a chance encounter with fictional late night legend jerry langford fuels rupert's delusions
06:54of grandeur leading him to violate the unspoken rule of polite society in a variety of creative
07:00and deeply cringe-worthy ways we have no record of your appointment oh well technically speaking
07:06i don't have an official appointment with jerry but he did ask me to call him personally and i
07:10was in the neighborhood i thought i'd just stop off a chilling eerily prescient takes on parasocial
07:16relationships martin scorsese's pitch dark comedy is an emotional roller coaster rupert is seemingly
07:22incapable of taking no for an answer you'll feel sorry for him in one scene and in utter disbelief
07:27at his lack of self-awareness in the net i want you out of here i want you out of here now is that
07:34plain enough i understand is that clear yeah yeah jerry i understand look look you're tired that's
07:40okay number four little miss sunshine whenever you want to start cooking your own food you're
07:45more than welcome sunset maddie you know like sunset manners so much you shouldn't have got
07:48yourself kicked out of there right for god's sakes awkwardness is clearly passed down from
07:53generation to generation little miss sunshine is proof of this each member of the beleaguered hoover
07:59clan struggles with their own personal battle whether it's grandfather edwin's substance use
08:03disorder or youngest olive's desire to compete in the titular beauty pageant cramped into a
08:08stuffy van on a cross-country trek to the pageant in question the hoover's volkswagen serves as a
08:13pressure cooker for cringe i feel sorry for you you do good yeah i do the sarcasm is the refuge
08:21of losers it is really yep as personalities types clash and personal revelations abound the family's
08:29bond perseveres despite countless obstacles that threaten to derail their journey winning the oscars
08:34for the best original screenplay and best supporting actor for alan arkin's performance
08:39little miss sunshine proves that embarrassment and the warm and fuzzies go hand in hand whatever
08:44happens you try to do something on your own which is more than most people ever do and i include
08:51myself in that category number three there's something about mary i got it stuck you got what
08:59stuck oh it um it's virtually impossible to talk about gross out comedy without bringing up peter
09:08and bobby farrelly just ask ted the protagonist of mary who finds himself in a compromising position
09:16right from the beginning the farrelly brothers are so committed to pushing the boundaries of
09:20awkwardness that we can't even show you what's debatably the movie's cringiest moment so we'll
09:26just have ben stiller and chris elliott explain it what do you mean clean the pipes you choke the
09:32chicken before any big date don't you tell me you spank the monkey before any big date although
09:40mary definitely tests the audience's tolerance for intolerable characters in hard-to-stomach
09:45situations it more than makes up for it with sheer laughs and hey how can we complain about
09:50a movie that casts jonathan richmond as its narrator and then does that with him what are
09:56you doing that's my girl he's kissing but you just slept with me i was only phoning you to get to
10:02mary number two the 40 year old virgin i dated this girl for a while and she was really a nasty
10:11freak she just loved to get down with sex all the time let's face it learning about the birds and
10:18bees is awkward it's probably exponentially more awkward if you need to have that conversation at
10:24age 40 this is the problem steve carell's andy faces once his friends and co-workers discover
10:29that he has never had sex their efforts to help him while well-intentioned pretty much only served
10:35to land andy in uncomfortable situations oh so you wrote hoe for show yeah i remember that girl
10:42she was a hoe for show surrounded by comedy heavy hitters like paul rudd and jane lynch
10:49carell's sweetness naivete and razor sharp comedic chops are what make andy's predicament
10:55believable in a role that made him a household name at the very least you'll never think of
11:01kelly clarkson the same way again
11:06no kelly clarkson before we unveil our top pick here are a few honorable mentions
11:11napoleon dynamite an instant cult classic of cringe watch this
11:24what the heck are you doing that's what i'm talking about shiver baby an impressively
11:29stressful dramedy starring a pitch-perfect rachel sonata um no that's that's so nice of
11:35you to offer i just i don't think that's anything that i would um like i don't really want to be
11:39like um a girl boss world's greatest dad this underrated satire explores the difficulty of
11:46doing the right thing okay but we're not buying a new computer yeah all right sounds fun this isn't
11:54the biggest screen jesus christ how about a thank you waiting for guffman a gut-busting
12:00improvised micro-mentary about a quirky regional theater trope which brings me to a point
12:05security oh i said we put a a rifle on here yeah a man with a rifle here and rifle here
12:14protect the whole square from greenville remember how much we got egged last year absolutely tim
12:20and eric's billion dollar movie stars heid becker and werheim bring their absurdist antics from tv
12:27to the big screen they will be running the mall from now on you take orders from them yes uncle
12:33damien i want to see where i live i don't know where to get food you do the song like we practiced
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12:58number one borat what color is your suit the suit is gray gray i would call it blue okay
13:04it's gray all right it's blue gray but it's certainly not black right all right
13:09let's say it's gray but it's not good if you thought that fictional cringe was too much for
13:14you to handle you may not be ready for borat's real life awkwardness disguised as a clueless
13:20mustachioed reporter sent to learn about american society by the government of kazakhstan sasha
13:25baron cohen won a golden glow for his chameleonic performance in addition he was nominated for an
13:31oscar for the film screenplay i like you do you like me i do like you you are my friend you're
13:37a nice young man and i am your friend you will be my boyfriend yeah i won't be your boyfriend
13:42ignorant inappropriate and imbecilic cohen's borat has a masterful gift for saying the wrong
13:48thing at precisely the wrong time generating unprecedented levels of discomfort and somehow
13:54managing to offend pretty much everyone whoever said awkwardness doesn't pay kazakhstan is number
14:03a exporter of potassium other central asian countries have inferior potassium did we miss
14:13your favorite awkward movie post it in the comments or don't if it'd be too awkward for you
14:20but don't forget to like and subscribe for more watch mojo videos so just come at me no okay well
14:27then i'll just oh my god stop it damn it oh sorry you have to like fight back did you enjoy this
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