The Best Socially Awkward Comedy Films of All Time

Comedy films these days come in a lot of varieties. There's romantic comedies, which are usually corny and predictable, there are slap stick comedies and gross humor, and there's comedies based on uncomfortable situations and socially ill-adept characters. The latter is by far my favorite but they're hard to find! So here's a little help for anyone with the same twisted sense of humor.

Black sheep are coming for you.... baaah!
Black sheep are coming for you.... baaah!

Black Sheep

In all honesty I have no idea if this movie is supposed to be funny, all I know is that it is. It's also one of the worst movies I have ever seen with absolutely deplorable acting, dialogue, scenery, you name it. It screams low budget. So why is it on my list? Because it is super socially awkward. Basically it answers the question of what happens when lonely biologists get too frisky with their fluffy pals... The obvious answer is the sheep give birth to mutated zombie-like offspring who then take revenge on the human race for their existence. It's gory with a lot of blood and intestine munching and whatnot... but because it's a flipping sheep it's hard not to laugh!

"All I said was 'This halibut is good enough for Jehovah!'"
"All I said was 'This halibut is good enough for Jehovah!'"

The Life of Brian

It's impossible to write about socially awkward comedy without giving a tip of the hat to the Monty Python films which probably made the genre popular in the first place. The Life of Brian was a perfect example - it was based on an idea. What if the messiah didn't believe or want to be the messiah? Instead of Jesus the messiah in this film is Brain and he's... well... not as patient as Jesus, in fact he's just a regular guy. There are many iconic scenes, one of the most memorable is a bunch of crucified men on crosses singing Always Look at the Bright Side of Life. It stands the test of time, this movie is still blasphemous and hilarious.

If only every funeral were this amusing the deceased would be boasting, "You'll never guess how I went out!"
If only every funeral were this amusing the deceased would be boasting, "You'll never guess how I went out!"

Death at a Funeral

The British are particularly talented at finding awkward situations and characters for their films and they don't shy away from taboos - even taboos you've never heard of. Death at a Funeral is exactly that. It follows the attendants at a funeral and shows you a very colorful slice of life. There's a man who has been accidentally given hallucinogenic drugs, there's a pervvy guy trying to hook up at a funeral, there's family tensions, and oh yes, there's also an attempt at extortion at the hands of the deceased's secret gay lover, who as luck would have it is also a little person. I don't know why this makes it funnier but it does. Just as you think things can not get any more awkward they do. This movie spirals rapidly out of control as you sit in your seat muttering, "Oh my God...." I think it is the funniest movie ever made but I could just be twisted. There is an American version of this film but I haven't seen it, nor do I know if it's any good. I have a hard time imagining this to be any family besides a stiff upper lipped British one.

Waking Ned Devine - the only movie which found an excuse to add an eighty year old man riding his motorcycle in the buff.
Waking Ned Devine - the only movie which found an excuse to add an eighty year old man riding his motorcycle in the buff.

Waking Ned Devine

This is a movie that is every bit as sweet as it is awkward. Imagine you live in a little coastal village and everyone's playing the lottery. Now imagine you win this multimillion dollar jackpot only to die of a heart attack seconds later. This is how Waking Ned Devine starts but it quickly gets more complicated from there. You see his friends in the town decide to pretend they are Ned Devine in order to get the cash but the situation quickly gets sticky and continues to make a bigger mess as it goes on. It's a charming little movie, very slow, very sweet, and just as touching as it is funny.

Wristcutters: A Love Story - possibly the sweetest movie ever to start with slashed wrists.
Wristcutters: A Love Story - possibly the sweetest movie ever to start with slashed wrists.

Wristcutters: A Love Story

I ended up watching this movie because the title caught me completely off guard. I was both intrigued and a bit nauseated to know what it meant. Little was I to know I was in for a real treat. This is an independent film that didn't get a lot of press but it has a small cult following which it is completely deserving of. Basically it starts when a man wakes up in Hell, or what he thinks is Hell. The funny part is that everything in the is new place is the same as in life except one or two shades worse than in reality. Plus no one can smile. It becomes a whimsical adventure to find his way out of Hell, dragging along with him a crazy singing Russian and a mysterious woman who has the same goal as he does. It's a weird winding story with a lot of bizarre humor including a black hole under the seat of the car - anything that gets dropped there is gone for good! I'm sure we can all relate. In any event this is actually an inspiring film, very sweet, very subtle, and incredibly imaginative. And the acting is just superb for an independent film.

Mary & Max

Have you ever wondered how a chronically tipsy mother would look to an eight year old? This movie answers that and so many more questions you never thought you asked! Mary's mother isn't a kleptomaniac, she's just borrowing, or conserving grocery bags by finding other places to carry the produce. Ahem. Mary and Max is an Australian claymation I would never show American children... it chronicles the spontanious penpal relationship between eight year old Mary and a random 40 year old guy she writes to in NYC. Of course her penpal Max has Asberger's and hence has no idea what is socially appropriate to tell little Mary when she asks things like where do babies come from? Apparently Atheist babies hatch out of eggs laid by dirty whores. Who knew! This movie is an unflinching look into a lot of characters who are severely flawed.... but with some great creative tooling it came out rather sweet and despite how dark it sometimes is (like when Max describes his childhood after his father abandons his mother and she takes a gun after herself) it also maintains a sort of sweet innocence. The combination of these two features makes for a wild psychological ride filled with guilty laughs.

Grandma's Boy

Grandma's Boy is another movie that escaped my attention until someone told me I should see it. It pokes gentle fun at the gaming world and has a lot to offer any stoners who might be in the audience. That being said it is based on a string of painfully awkward characters, events, and comments that collide at various points. The characters are really what makes this movie worthwhile. it is based on an older video game creator who works with a lot of young up and comers who lack life experience and social finesse, so he's often seen telling them wild stories about his personal life that they believe in like the tooth fairy. There's also his adorable but perhaps overwhelming grandmother and a really odd coworker who is a has-been prodigy who speaks in a robot voice when he gets anxious or thinks he's alone. It's... a piece of work.


OK, so I had to put one film on here that was a 100% stoner film. If stoner films aren't your thing then this movie is probably a bad choice however it is hilarious in how strange and awkward it is. It starts out with the accidental death of a cop's diabetic horse when one of the characters decides to feed him a treat and gets stranger from there. There's a guy living on the couch whose name and origin story is never identified and even a scene where two different characters both played by Dave Chappelle have an intensely bizarre conversation that generally leads any watchers both laugh and go, "what?!" All and all it is a silly stoner's movie but not one without a good chuckle for the sober people who might want to watch it.

Big Nothing

Having had this recommended to me I had to check it out. I was hoping it was not as disappointing as a wonderfully titled book I found, Death of a Nobody. I mean if you title something that attractively you better live up to it! This movie actually did... it's about two nobodies working dead end jobs that devise a very simple black mailing scheme involving a pervy priest and some saucy internet credit card purchases. However it doesn't go so smoothly and before anyone knows what's going on things spirally wildly and bizarrely out of control. Even the audience will be wondering, "What?! Who was that?! Why did that happen?!" while simultaneously laughing. This movie is whimsically mental, dark, twisted, irreverent, with a whalluping dose of gallows humor. You just can't go wrong there!


Saved is my favorite blasphemous movie. So what happens if you are going to a Catholic school because you've been kicked out of every other school in the area? And what happens when you meet up with a crippled atheist whose sister is one of the fiercest believin' popular girls? These are questions only asked on the sidelines as the actual story is about gay conversion. Sort of. Basically girl meets boy, boy would rather have other boy, and in order to do God's wishes girl then tries to convert boy by well... screwing him. The resulting pregnancy and everything that follows will have any unborn again Christians in tears. There's even touches of humor that will be equally offensive to all religions and ways of life, like the sign the wheelchair bound hero carries at the mall reading, "Will dance for food."


As we learned in the last movie teenage pregnancy can be hilarious. In this case it's not why the baby was created that's funny, it's the question what to do with it. This is a quirky almost sweet movie about a bitingly sarcastic accidental mama who decides to not only adopt her baby out but get to know the would-be parents. That's not awkward at all. Not one tiny bit. Just wait until it gets even more cringe worthy deeper into the movie. By the end you probably won't be sure what you should be feeling, aside from gas. I imagine junk food is what one eats while watching this, or perhaps cheap Mexican.

Four Rooms

Ever wonder what it'd be like to be a socially awkward British hotel host? I mean what could possibly be funny about that? Apparently everything. This movie tracks the main character's first night on the job as he caters to four rooms filled with absolutely crazy people. There's a coven of witches trying to conjure up their lost goddess who employ him to create their final ingredient for their spell. There's also a man who thinks he's the guy who his wife is cheating on him with who happens to be thoroughly armed. If that isn't bad enough the third room contains two mobster children who are precociously manipulative when they're not using hypodermic needles to play a game of darts or complaining about the dead hooker under their mattress. There's a fourth room too but that one was written by Quentin Tarintino and well... if you've seen one of his drunken blood sopping gore fests you've sort of seen them all. I fell asleep but if the moral dilemma you feel over being paid to chop some guy's finger off is mentally enticing to you then by all means feel free to watch until the end.

Never trust a woman with this look on her face - and especially never trust three women with this look on their face.
Never trust a woman with this look on her face - and especially never trust three women with this look on their face.

The Witches of Eastwick

This is one of those rare blockbuster American films that takes something darkly taboo and makes it awkwardly funny... Basically three best friends, all divorcees, find themselves seduced by the same man despite his profound lack of redeeming qualities. Add a little magic and all of a sudden the whole thing comes together and weaves into a totally different direction. It's a little offbeat, quite crude, and loved by many, a good thing to watch on ladies' night.

Coffee Date - answering the question of what it feels like to be the only straight man at a gay bar.
Coffee Date - answering the question of what it feels like to be the only straight man at a gay bar.

Coffee Date

Coffee Date is a movie based entirely on miscommunication and misunderstanding. Basically it's about a completely heterosexual guy who no one believes is straight. He spends the entire movie telling people he is but it becomes such a prevalent problem that even he starts to question himself. This is not one of those inspiring coming to terms with self sort of movies. In fact it is quite the opposite and will have you winging and cringing the entire time. Funny but very very awkward.

Shortbus - an unflinching film about the people who continue to ride it.
Shortbus - an unflinching film about the people who continue to ride it.


Shortbus is not for everyone. It is the most cringe-worthy comedy I have ever seen. It's not for the prudish or easily offended, that's for sure! In fact it is the most unflinching look at sexuality in all its forms that I have ever seen on film and it somehow manages to make it very funny and touching at the same time. When I asked my beau what movies I should put on this list he said, "What about that one that starts with a guy trying to give himself a blow job. That's awkward." I have to agree and the funny part is it didn't come off as pornographic so much as, "Wow... that was impressive...." The main character of this film is a woman who is a sex psychologist even though she's never had the sweet bliss of climax. This is a look at her patients, the people around her, and her struggle to achieve the big O. Between the fractured dominatrix, the gay trio, and the poor woman's clueless boyfriend this movie shed light on so much while still remaining funny, warm, and in some strange way inspiring. It all comes down to love - who can't agree with that?

Harold and Maude - teaching us that bubbles are better than cigarettes.
Harold and Maude - teaching us that bubbles are better than cigarettes.

Harold and Maude

Harold and Maude is one of my favorite old movies. It is about a nineteen year old boy whose favorite hobbies are attending funerals, faking his own death, and tricking out his car to look like a hearse. This is when he meets Maude, a very vibrant woman in her late seventies, who teaches him what life's all about - did I mention he falls madly in love with her? Yeah. Between laughing at the faked death scenes and cringing at him pursuing a geriatric woman you're bound to love this movie. It has a cult following because of how awkward, how sweet, and hilarious it is. This was possibly the first movie to have its entire soundtrack written by one person, in this case Cat Stevens. So try this out - it's just that adorable.

Little Miss Sunshine - proving you don't need beauty pageants to show you're beautiful.
Little Miss Sunshine - proving you don't need beauty pageants to show you're beautiful.

Little Miss Sunshine

Little Miss Sunshine is a movie that claims to be about a small girl who wants to participate in a beauty pageant but it's about so much more than that. It's about her warped family, all their issues, and at times it is also about the greater issues of the society they live in. For instance the little girl in question is not the sort of child that would win a beauty pageant. She's a hyperactive, enthusiastic, chubby child who has no idea what she's asking for. There are homages to old gags - like when grandpa dies mid-trip and they have to decide what to do with the corpse, as well as a lot of additional dark humor. It's tragic, it's funny, it's strange, it's excruciating. Something for everyone!

Billy Elliot - Social norms aren't worth fussing about.
Billy Elliot - Social norms aren't worth fussing about.

Billy Elliot

Billy Elliot is really one of those movies that shows beautifully that tragedy and comedy are two sides of the same coin. Billy is a lower class British boy who lives with his gruff and sometimes abusive father, his passionate teenage brother, and his dementia addled grandmother. His mother had died, his father was on strike, and tensions in the house are rife when Billy takes up ballet. Things get tough from here as you follow him on his journey. As tragic as it is it was also a movie that is very touching and inspirational. And then there are points that are just downright funny like when Billy's ballet teacher summarizes The Swan Lake in only the crudest and most unflattering way.


I think most of us have memories of someone we went to school with that always made us think, "What the hell is wrong with this kid?!" This movie is about that kid - the one whose most normal line is, "Actually I've been dead for several years now." The movie starts out as our protagonist takes an almost mathematical approach to picking a romantic partner and is rewarded when said love interest decides to use him as a chew toy to blackmail herself in some sort of back-handed Machiavellian scheme. From here love blossoms, because why wouldn't it, and the two continue tackle life's often bizarre obstacles - like how to stop your mum from cheating on your dad with a ninja and whether or not killing your girlfriend's dog could be beneficial to her. Wrap this up with a lovely soundtrack and offbeat filming methods and you end up with a cult classic. A must watch for those who love awkwardness, British humor, scattered plotlines, and things that make you want to cringe.

Comments 11 comments

DrMark1961 profile image

DrMark1961 3 years ago from The Beach of Brazil

Wow, your sense of comedy is almost as demented as mine. I can´t believe I missed Wristcutters, though. It sounds like a perferct movie, with absolutely no socially redeeming value!

Georgie Lowery profile image

Georgie Lowery 3 years ago from Slaton, Texas USA

I like interesting movies. The only one here I've seen is Little Miss Sunshine and I absolutely loved it. I took a chance and watched the trailer you shared for Billy Elliot and I think that may be the next movie I watch. Thank you for having great taste and for sharing it! :)

Theophanes profile image

Theophanes 3 years ago from New England Author

DrMark1961: Oh wristcutters is wonderful, a real gem. You'll love it. It's always nice to come across other people with a warped sense of humor. Do let me know if I have missed anything! :)

Georgie Lowery: Thank you for commenting and enjoy Billy Elliot! It's a really sweet movie besides being funny.

Mhatter99 profile image

Mhatter99 3 years ago from San Francisco

Good choices. Thank you for this.

Theophanes profile image

Theophanes 3 years ago from New England Author

No problem. Enjoy them. :)

Elias Zanetti profile image

Elias Zanetti 3 years ago from Athens, Greece

Most of Wes Anderson's films could also tagged as 'socially awkward' as well as Napoleon Dynamite. Wristcuttersis indeed avery nice movie (with a great soundtrack). My favorite in your list is probably Little Miss Sunshine :) and you got me really curious about Black Sheep.

Nice hub! Thanks.

Theophanes profile image

Theophanes 3 years ago from New England Author

Hmmm, I haven't seen any Wes Anderson films or Napoleon Dynamite. I will have to put it on my list of things to watch!

Wristcutters did have a lovely soundtrack. You can't help but love that. And black sheep is probably the worst produced movie I have ever seen but if really bad B-rated (or Z-rated?) films amuse you then by all means check it out! I just loved the photo I found for it... perfect cover photo for this article.

MJennifer profile image

MJennifer 3 years ago from Arizona

How do I love this hub? Let me count the ways! Apparently you have the same sense of humor I do ... I'm sorry. I also enjoy these sorts of movies because so often they capture humanity so much better than the typical "play by the rules" scripts. There are several here I haven't seen ... yet; and some that are my "most favorite" already -- Harold and Maude, and waking Ned Devine among them.

On "my" socially awkward movie list, I'd include Eating Raoul ("It's amazing what you can do with a cheap piece of meat"), Meet the Parents ("Cats don't have thumbs, Fokker!"), What's Eating Gilbert Grape, and the Rocky Horror Picture Show (just a sweet transvestite ... from Transylvania), and Burn After Reading (the chair. OMG, the rocking chair.) ... among a few memorable others.

Great job! -- MJ

Theophanes profile image

Theophanes 3 years ago from New England Author

No apologies necessary MJennifer - it's always a real hoot to find someone else who has a twisted sense of humor similar to your own. Movies are a wonderful way to share that but wow... most comedies these days are downright stuuupid, which is fine if that's what you like but it leaves a gap for people who prefer awkward humor.

I appreciate the recommendations. I am definitely going to have to put those on my to-watch list! Funny, I have seen and laughed at Rocky Horror so many times but I have never really considered it a comedy! Maybe that's a failure on my part!

Alisha Adkins profile image

Alisha Adkins 2 years ago from New Orleans

Great list - you've given me a couple of new titles to add to my Netflix queue!

Theophanes profile image

Theophanes 2 years ago from New England Author

Wonderful! I hope you enjoy them! :)

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