The 9 Most Unexpectedly Upsetting Comedies Of The Last 25 Years
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The 9 Most Unexpectedly Upsetting Comedies Of The Last 25 Years

By Joanna Robinson | Seriously Random Lists | August 26, 2013 | Comments ()


Bridesmaids: Originally marketed as a delightful slapstick comedy featuring a slew of Groundlings and “SNL” alums, “Bridesmaids” took a lot of people by surprise. Sure, many of the tears I shed while watching came from laughing too hard, but there’s a reason this film and Wiig’s performance came up again and again in the comments section of our recent “Too Close For Comfort” column. In between bathroom humor and pill-induced meltdowns, sh*t gets really dark. Wiig’s character keeps bumping against rock bottom only to find there’s another layer further down. So if you’ve ever found your life sort of spiraling out of control financially, personally, romantically, professionally, then this movie can be stunningly hard to watch. I’m not sure anyone who slapped that repugnant “homance” label on this film had a single solitary idea what this movie was really about.
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Sideways: Writer/director Alexander Payne should have been a major clue as to the downturn in tone this wine country romp would eventually take. That being said, those who expected to see Giamatti and that blonde guy from “Wings” frolic, swish and spit were in for a rude awakening and a deeply upsetting finish.

Stranger Than Fiction: Though we should have learned our lesson two years earlier when Jim Carrey damn near broke our hearts in Eternal Sunshine Of The Spotless Mind, Will Ferrell’s involvement in this movie was a huge misdirection. Though the film is plenty whimsical and endearingly romantic, there are a lot of heavy themes about unfulfilled potential and lives half-lived. And let’s not even go into the anguish of watching a suicidal Emma Thompson, shall we?

The World’s End: Fans of the previous collaborations between Simon Pegg, Nick Frost and Edgar Wright were in for a bit of a nasty shock this weekend when watching the conclusion of their Cornetto Trilogy. Don’t get me wrong, I absolutely adored this final installment. In fact, I think the darker elements are what make it so great. Like most Edgar Wright movies, I want to watch it a few more times until everything clicks into place, but for now I’m left both highly entertained and deeply unsettled by this tale of frustrated manhood. The film has the usual jokes and gags but it lacks the frothy, heady tone of Hot Fuzz and Shaun Of The Dead. And isn’t that exactly how the end ought to be? A little more melancholic and reflective?

My Girl: This was mostly a bait and switch pulled on kids of the 90s and their parents. Though it was pitched as a sweetly nostalgic coming of age flick, it had a truly Terabithian ending. It was downright Marlovian. I wonder how many flummoxed parents were left with quivering wailing children on their hands?

50/50: Okay, so it’s a cancer comedy. So how exactly could the upsetting elements be all that unexpected? I dunno, did you watch the same trailers I did? I was prepared for whimsical head-shavings and a little soul-searching. I was not, however, prepared to lose it completely. But lose it I did. Sorry, Angelica Huston cries, I cry.

Life Is Beautiful: As above, the setting for this movie should have been the first tip-off. But I’m not sure the Holocaust element was made explicit in the marketing. What I do know is that I had seen Benigni’s antics in other films and I thought I was in for a lot of clowning and buongiorno principessa-ing. Not…this. Oh god.

Planes, Trains And Automobiles: This film is a sentimental favorite around Pajiba and with good reason. Here are two fantastic comedians at the top of their game. Here are cars on fire and epic airport rants and most emphatically not pillows. But the very upsetting ending of this movie, once seen, cannot be unseen. And so the whole slapstick nature takes on a darker, more melancholic meaning. But it’s that somber aspect anchoring the fizzy comedy that makes this one of the finest comedies of all time.
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Up: Pixar has always mixed a little poignancy in with their films. A little heart tug is guaranteed. But I’m not sure any of us expected to have our hearts yanked out of our bodies through our tear ducts in that gut-punch of an opening montage. I’ve never seen a movie theater go from zero to sobbing that quickly.

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Comments Are Welcome, Bigots and Trolls Are Not

  • hoppergrass

    I nominate SLC Punk. So much ugly cry.

  • YeahButNoBut

    Muriel's Wedding, anyone? First half a comedy balancing on a wire, second half a tragedy built on the toppling comedy of the first half.

  • princessdi81

    Was Almost Famous marketed as a comedy? Because that movie tore my world apart.

  • Jo 'Mama' Besser

    Man, I tried watching that movie three times and fell asleep every time. I can't do this.

  • CoolMinded

    My Girl is the reason why I don't like open caskets.

  • Ro

    How is In Bruges not on this list!? I came late to the In Bruges party and everyone told me how hilarious it was, no on warned me it would break my heart and trample my soul.

  • Conor

    The bit in The World's End with the sleeves (you'll know if you've seen it), and Pegg's performance at that point, just ripped my heart out and punted into the bin.

    Way, way too close to home for me and my mates.

  • It wasn't a particularly good movie, but Georgia Rule sure took an unexpected turn for me. From the marketing, I expected a heart-warming (supposedly) family drama, not whatever the hell that was.

    Also, Uncle Buck gives me the sniffles every time. Shut up. I know I'm ridiculous, okay?

  • manting

    kicking and screaming - the one about life after college - not the will Farrell/Ditka soccer movie.

  • Long_Pig_Tailor


    Seriously, all it takes. You throw that at me, I'm done.

  • John W

    I would add Midnight Run to that list. That scene where De Niro sees his daughter always gets to me.

  • llp

    This list makes me cry. I held it together until Life is Beautiful. C'mon guys. Where is a funnier list?

  • sonotamused

    Up remains on my list of "movies I wish I hadn't wasted my money on" - it wasn't heart wrenching. It aimed for it, but just end up being cloying when it should have been emotional and the humor in it was just awful. Blah.


  • Bodhi

    I don't think I will EVER recover from the trauma that Pixar inflicted upon me with Up. I know that sounds seriously melodramatic, but its true. I thought about watching it again recently, but I just don't think I can bring myself to do it.

  • Ami

    The rom-com that made me lose my shit was "Friends with Kids". I could. Not. Handle. the wildly familiar, yet hopelessly dysfunctional relationships. Hit waaaay too close to home.

  • I knew the Up montage was incredibly moving, but I had no idea it would ruin the whole movie for me.

    Great movie, by the way. I'm never watching it again.

  • Long_Pig_Tailor

    I still haven't seen it. I went a few years without ever having seen it, and then recently I saw only the opening montage.

    Fuck. You. Pixar. Also the FX Network. I do not need to be randomly crying on a Saturday morning, damn you. Never finishing.

  • Bodhi

    Ditto. All the way

  • PDamian

    Bridesmaids really did a number on me. I didn't identify with Kristin Wiig's character, though. For me it was Melissa McCarthy's character (sorry, don't remember the names). While no-one flicked firecrackers at me, I was the recipient of more that my fair share of bullying, being the designated smart-but-fat chick. I'm not as successful as McCarthy's character, but I'm doing well, and can afford to help my mom out financially. I've won awards in my field, and I get laid from time to time (and yes, I'm still fat). It really does get better, if you can just keep the haters from destroying you -- and I don't say that lightly, as I know just how hard that can be.

  • Salad_Is_Murder

    I hate Bridesmaids because A) I don't find it that funny and B) I hate
    Wiig's character so, so much. She's so selfish and entitled and toxic
    all the while we're supposed to be pretending that she's goofily
    charming or sympathetic and it's got this bullshit Disney ending where
    every says they're sorry and they all love each other and everyone's
    happy and it's garbage.

  • $27019454

    It's total fucking garbage. Just my opinion, of course. But she's a selfish bitch.

  • Wigamer

    THANK YOU. I hate that character so much, I'm pretty sure it's responsible for my unreasonable hatred of Wiig herself.

  • Siege

    The marketing for "Everybody's Fine" made it seem like a "wacky family" movie. IT WAS NOT. Much like "Running With Scissors" turned out to be a lot more depressing than the commercials had led me to believe.

  • Lisa Bee

    For years I never cried once at a movie in theatres, and then 50/50 came along and left me choking on sobs. I tried to blame my sniffles on the fact that I was sick and had a cold... but my sister knew better.
    And so marked the beginnings of my reinvention as a newfound weep-monster.

  • $65530708

    No Three Kings?

  • Fabius_Maximus

    Hell, yes.

    I watched it with a bunch of friends who decidedly not liked the turn the movie took. I loved it, because it undermined my and everyone else's expectations in an interesting way.

  • $65530708

    I'm officially adding it.

    10. Three Kings

  • Bea Pants

    Super. Technically a dark comedy so I should've been expecting upsetting but I was not prepared for what happened to Bolty.

  • Idle Primate

    and Defendor. marketed as a comedy. not what was delivered

  • Ruthie O

    Oh GOD. Life Is Fucking Beautiful. When my husband and I were in Rome last January, I described the plot to him. He had never seen the movie and never planned to. By the end, I was crying. Just DESCRIBING that scene (you know which one) reduced me to a quivering ball of feelings.

  • I was watching that movie while cleaning guns one night. I came within a hair of shooting the TV like I was Elvis when I hit that scene.

  • adam

    Leaves of Grass, starts off as a wacky twins-switching-places-growing-pot funny-misunderstanding-hilarity had by all kind of movie. And then takes a sharp turn into a very dark corner, i was kind of stunned when it happened as the audience is given little warning that things are gonna get so violent.

  • Stephanie

    I made my husband watch "Planes Trains and Automobiles" during our first Thanksgiving together. I completely forgot to warn him about the sad factor. Near the end, I look over and he's like crying into his cranberry sauce and saying "What the fuck?" over and over.

  • ZbornakSyndrome

    Did anyone see Unfinished Song with Terence Stamp? It was billed as a cute British geriatric comedy, A Quartet part 2 if you will. It wasn't. It was 40 minutes of watching someone die of cancer and their loved ones fall completely to pieces.

    People were sobbing audibly in the screening and passing tissues to each other across the aisle - it was the weirdest experience I've ever had in a movie theater.

  • Classic

    Thank you rat (swear word) for making me cry at work. A day after the antics of Crazy Squirrel I thought I would be immune to feeling anything ever again. You proved me wrong.

  • Bert_McGurt

    F*ckin' bees, man. F*ckin' BEES. It's like someone kicked my heart in its balls.

  • sistercoyote

    Around my family and friend group, there are different categories of movies:

    Good movies, excellent movies, WTF-am-I-watching movies, bad movies (which are on the good side of bad), god-awful movies (which are the bad side of bad), Even-Dad-Hates-It movies (which would include exactly one film: Dudley Do-Right), and Stupid Movies.

    If we're talking about films, and someone says "X is a stupid movie," then "X" made them cry.

    "Up" is a really goddamned stupid movie.

  • jaimejoshi

    "He can't see without his glasses." That's all it takes. That short sentence brings forth a lump in my throat and tears prickling my eyes.

  • damnitjanet

    My husband was watching some movie when I got up Saturday morning. They were herding people into showers, separating men from women and children. I said, "Why are you watching something like this at 8 am?" Then I saw Roberto Benigni. I promptly left the room, and refused to return until he changed the channel.

    Along those lines, DO NOT get suckered into "The Boy in the Striped Pajamas." Ever.

  • Wigamer

    Nope. Never watching Life Is Beautiful. Never gonna happen.

  • Cree83

    The Boy in the Striped Pajamas didn't get to me, only because I just couldn't suspend disbelief. I've swallowed far more unbelievable plot lines, but I couldn't stop wondering, how did a German kid talk to a Polish kid? What? Did the Polish kid just happen to speak German? Was that common, for a kid that age? Couldn't get past it.

  • Sean

    Those first 8 minutes of up. Maybe the best love story in the history of film.

  • Danar the Barbarian

    I DVRd it but haven't watched it yet. I know he loses his wife in the beginning of the movie and I just can't get up the guts to see it. My Mom died 3 years ago and just seeing the old man kissing his wife in that photo above tells me I'm not ready. Maybe never? Sigh.

  • minxy

    Fifty first dates: the wacky, feel good rape romp.

  • minxy

    Wait downvoting person, let me explain why I hate this movie so! Imagine you are Drew Barrymore's character and you wake up seven months pregnant beside a stranger who tells you that you are definitely his wife and you totally want to have his baby even though you don't remember ever meeting him before. That's complete nightmare fodder. It's like a horror movie.

  • Sean

    Just think of the legal aspects of it. Drew Barrymore's character would have been declared legally incompetent. She would have to have a caregiver. She would not legally be able to consent to sex.

    This and the Goldie Hawn/Kurt Russell movie-Overboard. Rape movies that are supposed to be romantic comedies. Stupid sick shit.

  • BiblioGlow

    That's why her dad was always with them - so she could be sure she hadn't been kidnapped and brainwashed or something. But yeah, that movie had sooo much dark potential that it hardly even brushed against. Yes, they included a few Barrymore freakout scenes, but then again - everything with that damn walrus.

  • Long_Pig_Tailor

    And yet, what about when her dad is finally dead and gone? Even with the nifty video tape recaps and everything... Man. They show it all as a happy ending, but I'd bet money she spends more days holed in her room on a boat in the middle of the goddamn arctic, just sobbing and having breakdowns than she does having breakfast with what she can't even be certain are her children.

  • chanohack

    All "happy endings" are only temporary anyway.

  • BiblioGlow

    Exactly - but is it worse than just stopping her life altogether? Not progressing, not accomplishing or producing anything, living in the limbo her Dad and brother had created for her before? Would you be more angry and confused and sad to wake up every day and find that you were living a day-to-day life you had no memories of, or be grateful that at least your life was still happening? Either way she's going to wake up one day and be seventy years old, so it's not like she could've stayed in limbo forever. Would you rather wake up and find yourself seventy and be in possession of a life that was irrelevant, inconsequential, or have a life that approached normal but that you didn't remember a single moment of? I was trying to figure all that out when I watched it, but then I realized how much time I was devoting to thinking about an Adam Sandler movie and I stopped. I would love to see an intelligent take on the scenario, though.

  • Sara_Tonin00

    pretty much someone said, how can we make a happy version of Memento?

  • Sara_Tonin00

    I'm pretty sure waking up every day not being able to remember the passage of time period is the nightmare fodder - inexplicably older & grayer every single day. Waking up really ill even though you remember going to bed healthy. Waking up to find your family members are dead even though you remember them being all alive. There's really no win in this situation at all, ya know?

  • delle

    Oh I want to call my memory and say thanks for always being there for me. And say sorry for all the times I got mad at it because I forgot to pick up milk or had to look up a phone number 3 times before being able to dial it through.

  • Malin

    Just thinking of Up makes me teary-eyed. That one picture was enough to have me close to sobbing. I loved that film, but I still haven't been able to rewatch it, because I'll have to watch that heart-wrenching sequence again.

  • ZbornakSyndrome

    I saw Up on a date and ended up a blubbering, snotty mess in the first five minutes. I turned to my date and noticed that he was weeping into his popcorn as well. It was a great bonding moment.

  • Pants-are-a-must

    It's amazing how both "Up" and "Star Trek" came out in the same summer to wild success, did the same expository trick, and it worked both times to the extent that it STILL works upon rewatching.

  • Jo 'Mama' Besser

    Why can't I cry?!

  • Salieri2

    "Tiberius? You kidding me? No, that's the worst. Let's name him after your dad. Let's call him Jim."

  • chanohack

    One time my boyfriend walked into the room right after that scene to find me very emotional. He thinks I'm ridiculous, but I'd be so SAD if he ever got killed by time-traveling Romulans in space!

  • Pants-are-a-must


  • FireLizardQueen

    I was coming here to write the same comment. Verbatim. Totally teary eyed right now.

  • PerpetualIntern

    That .gif just depressed me so much.

  • Pants-are-a-must

    Re: the need to rewatch Edgar Wright's movies: A friend who watched "The World's End" with me pointed out that all the pub names directly refer to what was happening in them.

  • kbenton

    I loved that little nod... I started paying attention at The Old Familiar and wasn't disappointed to ferret out the little tidbits.

    And the poster on the wall outside the Mermaid...

  • Classic

    Shit I didn't even notice! Fuck I must re-watch the movie, off to the theater again!

  • $65530708

    It is a movie that will require multiple viewings. I just wish you could get the Blu-ray now.

  • PDamian

    I cannot wait for the Blu-ray. I have both Shaun of the Dead and Hot Fuzz on Blu-ray, so I know from experience that the extras are going to be phenomenal, and the gag reel alone worth the purchase.

  • OH GODDAMMIT now I need to go watch again. I picked up on a bunch of stuff when watching, but not that. And a quick wikipedia makes it abundantly clear that this is true. Back to the theater!

  • Pants-are-a-must

    I would also like to nominate "Tangled" for this list, simply on the account of Repunzel's goddamn FATHER.

  • cgthegeek

    Now I'm picturing his face, and now there's something in my eye.

  • the dude

    The up montage didn't make me cry, because it just felt so damn manipulative.

    By the way, what's the difference between melancholy and melancholic? Aren't they used interchangeably?

  • Jo 'Mama' Besser

    Thank-you. The cartoon we've been watching for 35 seconds can't have a baby, you'd better cry, mucous-filled weep dumpsters. And if you don't, everyone in the theatre sitting nearby will start looking at you like you're missing your heart parts.

    Um, allegedly.

  • BWeaves

    Melancholy can be a noun (a feeling of pensive sadness, or historically = black bile) or an adjective (having a feeling of melancholy).

    Melancholic is also an adjective, and is a derivative of melancholy.

    So, no difference really.

  • Jo 'Mama' Besser

    Tell that to the over-zealous bloodletter on the sanguine smash hit (well, spike) That's My Humours! Eight leeches was enough, but ten was too many.

  • Luke Bailey

    Like it or hate it ... it doesn't get much more unexpectedly depressing than the Adam Sandler movie "Click"

  • Jo 'Mama' Besser

    Adam Sandler depresses me, too.

  • Deidra

    Spanglish is in that camp too.

  • Long_Pig_Tailor

    God, Spanglish. On the one hand, girl wrote one hell of an admissions essay. On the other, that ending might've pissed off/depressed the reader enough to be all, "Try your luck at Yale."

  • Sara_Tonin00

    I really need to rewatch Stranger than Fiction. I enjoyed it so much the first time.

  • Jo 'Mama' Besser


  • apsutter

    Love this movie! Saw it in the theater and have re-watched it many times since then. Will is great in it and I was so happy that Dustin Hoffman played the professor.

  • Wild Rumpus

    When Mr. Crick runs up to Ana outside the bakery and awkwardly says, "I brought you flours," I knew I was 100% invested in these characters. I just loved that movie. It really warmed the cockles.

  • Oh, man, the flours. That was wonderful.

  • Sara_Tonin00

    At one point I meant to memorize her monologue about switching to a career in baking. *Another* reason to revisit.

  • pajiba

    JOHN CANDY. That look just breaks my damn heart.

  • Wigamer

    I like that Dell Griffith.

  • Aaron Schulz

    he listens to much and it makes me want to hug him, although i feel like both him and steve martin are just kinda jerks through most of that movie

  • bbmcrae

    Your sentence breaks my heart.

  • kirbyjay

    John I miss him

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