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The 9 Most Unexpectedly Upsetting Comedies Of The Last 25 Years

By Joanna Robinson | Lists | August 26, 2013 |

By Joanna Robinson | Lists | August 26, 2013 |

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.