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Top 10 Saddest South Park Moments

VO: Rebecca Brayton WRITTEN BY: Caitlin Johnson
Even the funniest comedies can still break your heart. Welcome to WatchMojo and today we’ll be counting down our picks for the top 10 saddest “South Park” moments. For this list, we’re only looking at scripted moments from the show itself, meaning that – while tear-jerking – tributes to deceased cast members won’t be included, nor will moments from the movie.

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Even the funniest comedies can still break your heart. Welcome to WatchMojo and today we’ll be counting down our picks for the top 10 saddest “South Park” moments.

For this list, we’re only looking at scripted moments from the show itself, meaning that – while tear-jerking – tributes to deceased cast members won’t be included, nor will moments from the movie.

#10: Beautiful Sadness “Raisins”

In spite of all its crude humor and persistent attempts to offend anyone and everyone, “South Park” still contains some undeniably sweet and even philosophical moments. One of these comes at the end of the episode “Raisins,” which follows Stan as he sinks into a depression after being dumped by Wendy, after which he joins the Goth Kids. But when Butters is also dumped, he tells Stan and the goths: that no matter how sad he is, he’s still happy that something could make him feel that way. This is because it means that he felt something really good before. Wise words Butters, wise words.

#9: Wendy Uses Photoshop “The Hobbit”

Over the years, Wendy has taken up a lot of causes and stands on a lot of soapboxes, often succeeding at making her voice heard. But not this time! She aims to stop the trend of young girlsPhotoshopping images of themselves after the other fourth graders jump on the bandwagon, but to no avail. With the boys all fooled by the obviously fake pictures, Wendy becomes increasingly frustrated until she’s finally forced to give up. We see her abandon her mission and tearfully Photoshop her own picture, sending it out to the other kids right before the credits roll. Talk about a disheartening.

#8: The Mountain Lion’s Death “Woodland Critter Christmas”

“Woodland Critter Christmas” is probably the most un-family friendly Christmas special to ever air, featuring a Satanic cult of Disney-esque animals trying to birth their savior, the Anti-Christ. Stan becomes their unwitting assistant when he’s sent out to slay a mountain lion who keeps killing pregnant members of the Critters. After Stan murders the lion, which seems like the right thing to do at the time, a trio of lion cubs crawl out of the cave to mourn their mother. Stan is just as horrified as the audience by what he’s done, as the orphaned lions sob uncontrollably over their dead parent.

#7: Cancer "Stanley's Cup"

In one of the show’s most polarizing episodes, Stan finds himself coaching a hockey team of kindergarteners. While this may sound relatively simple, problems arise when one player, Nelson, has terminal cancer. Nelson’s fate apparently hinges on the team, as he begs Stan to let him see them win just one match. At the end of the episode, pro-hockey team the Colorado Avalanche nobly step aside and let the kids finish their game against the Detroit Red Wings. Unfortunately, the Red Wings are just as brutal with the pre-schoolers as they were with the pro team, and Nelson – watching the game from his hospital bed – dies. Can you say bleak?

#6: “Butters’ Very Own Episode” “Butters’ Very Own Episode”

Butters embodies the innocence and naivete you’d expect from a fourth-grader, and while all the other boys get progressively jaded, he’s largely remained the same old Butters. But his optimism is undercut by the tragedy of his home life: his closeted gay father and an increasingly unhinged mother. In “Butters’ Very Own Episode”, Mrs. Stotch seemingly drowns Butters, and then she and her husband go to great lengths to cover up her crime until Butters finds his way back home. Awful as it is, it’s clear that they do love their son at least a little, proven by Linda Stotch’s heartfelt emotional breakdown when Butters fakes his own death in season 9.

#5: Grandpa Marsh’s Alzheimer’s “Cash for Gold”

Stan’s grandpa’s forgetfulness has been played for laughs frequently throughout the show, but in later seasons it becomes much more upsetting when we finally learn he’s been diagnosed with Alzheimer’s disease. He just can’t keep straight who’s who anymore, always calling Stan “Billy” and commenting about how Shelly is still just a baby, until Stan reminds him that she’s actually thirteen. But the most bittersweet moment comes in “Cash for Gold” when he reminisces about a dog named Patches that he once loved but whose appearance he can no longer recall. So Stan gives him a framed photo of Patches and his younger self so that he’ll always remember. Talk about a tearjerker.

#4: Kenny & Karen “The Poor Kid”

Of the core cast, Kenny is the one whose home life we see the least of. Sadly, the McCormick kids are a lower priority to their parents than their addiction to crystal meth, which eventually results in the kids being taken away and fostered. Though it’s hard on all three kids, it’s the youngest, Karen, who suffers the most; she is both bullied at school and neglected at home. In “The Poor Kid,” Kenny becomes Karen’s guardian angel, donning his Mysterion get-up to comfort her in times of need. Then, in a later episode, we see Kenny work tirelessly at City Wok, all to save up enough money to buy his sister a doll.

#3: Chef’s Death “The Return of Chef”

When Isaac Hayes left the show after taking issue with its mockery of Scientology, Parker and Stone were forced to find a way to write his beloved character Chef out of the episodes. They did this with an episode about Chef joining the “Super Adventure Club,” a pedophile cult-like group. While the boys try to rescue Chef from his brainwashing, the rope bridge he’s crossing is struck by lightning and breaks, with Chef ending up impaled on a branch in the ravine below. He miraculously survives this – at least, until a mountain lion and a grizzly bear show up and rip him brutally to pieces. Talk about a brutal goodbye.

#2: The End of “You’re Getting Old” “You’re Getting Old”

Meant to reflect Parker and Stone’s own fears of getting older, Stan has an existential crisis when he turns ten. This leads to him thinking everything looks and sounds “like shit”, and his friends stop hanging out with him after he becomes such a bummer. Things only get worse when his parents fight and decide to get a divorce. The episode ends with a montage of Stan, Shelly and Sharon moving out on their own and leaving Randy behind, while Fleetwood Mac’s “Landslide” plays in the background. Even more upsetting is the fact that this was a mid-season finale, meaning fans had to wait months for a resolution.

#1: Kenny’s Death for Real “Kenny Dies”

Kenny’s died a lot, but never quite like this. With the show looking to kill off a major character, Kenny was lined up for the chopping block after Parker and Stone said they were running out of original ideas for his many deaths. The result was an episode that directly tackles the loss of a close friend and its impact, especially on young children. Kenny’s illness and deterioration are enough to move even Eric Cartman to tears, while Stan eventually refuses to visit Kenny anymore because it becomes too upsetting. It actually looked like Kenny was gone for good, as he didn’t appear again until the finale of the following season.

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