When South Park Got Serious: 20 Saddest Moments

Welcome to WatchMojo and today we’re counting down our picks for the tear-inducing, sad, somber moment from “South Park”. There will be some spoilers, so here’s your warning. What’s your saddest South Park moment? Let us know in the comments!

#20: Stan’s Outlook

Throughout this episode, Stan is feeling down. Instead of actually helping him with his depression, the diagnosis is Asperger’s syndrome. With the help of a “Matrix” style vigilante group, he turns to alcohol so he can feel like he used to before everything turned crappy. He reaches a point where he accepts that change brings new opportunities. His newfound optimism is crushed when his parents tell him they’re getting back together because sometimes it’s better to stick with what you know. Just when it seemed like he was going to start a new chapter, the moment is ripped away and the only way Stan can cope is by taking a swig from a whiskey bottle before joining his friends.

#19: Kenny’s Present

In order to improve the cultural reputation of South Park, the town decides to revamp a rundown district, branding it as SoDoSoPa. Kenny and his family are put at a real disadvantage by the gentrification of their neighborhood as it makes things more expensive for them. So Kenny goes out and gets a job at City Wok. Although he works hard, he isn’t paid very much. At first we don’t know why he decided to go out and get a job. However, in the end we see he used the money he earned to buy his sister a doll. It’s a surprising, sweet and selfless gesture, and it brings a tear to your eye.

#18: Whale Fall

At Sea Park, Kyle gets up close to the orca Jambu. It appears as though the killer whale can talk but really it’s just some employees messing with Kyle, who now believes Jambu wants to go to space. The kids make it their mission to get Jambu to the moon so he can be reunited with his family on the Moon. They take Jambu from the park and make their way to Mexico where Jambu is launched to the Moon. The boys celebrate a job well done but in the closing shot we see the whale has died on the Moon’s surface. They had good intentions but it’s a grim fate for Jambu.

#17: Cartman’s Sacrifice

Following the Covid-19 pandemic, a lot has changed in South Park. Stan and Kyle have had a falling out, and Kenny has died. One of the bigger surprises is that Cartman has converted to Judaism, become a rabbi and has a wife and kids. Kyle certainly can’t believe it and thinks it’s some kind of ruse. Eventually it’s found out that Kenny was working on time travel to prevent the pandemic from happening. When Stan and Kyle want to undo their current timeline, Cartman opposes them since he’s finally happy. Eric eventually relents and the past is changed. In the future of this new timeline, Cartman is bitter and misuses alcohol. The worst thing is, no one knows what he sacrificed.

#16: Kip Loses a Friend

Kyle adds Kip Drordy as a friend on Facebook which, socially, turns out to be a bad move as he soon starts to lose friends on the social media site. For Kip, Kyle’s online friendship means everything to him as he’s the only friend he has. It’s endearing how much joy Kip gets from the online relationship. Kyle however has to end being friends with Kip because he can no longer take the negative association with being attached to someone who only has one friend on Facebook. It’s just so sad when Kip gets Kyle’s message ending the friendship. Luckily, Kip gets all of Stan’s friends, so there’s a silver lining.

#15: Cartman’s Feelings for Wendy

There’s a debate held at the elementary school on whether or not the flag of South Park should be changed. Wendy and Cartman end up on the same team and at first she’s less than thrilled about having to work with him. Through the course of working together, they start to discover that they have common interests and a bond starts to form between them. Wendy even has a romantic dream about Eric. At the actual debate, she ends up kissing him to get her feelings out of her system. When she reveals she no longer has any feelings for him, he plays it cool as you might expect. But once she leaves, we see how dejected he really is.

#14: Tweek & Craig Breakup

Tweek and Craig are labeled as being in a relationship by other students at school. The two boys are adamant that they are not actually gay, but nearly everyone else in town is happy for them. In order to get out of the situation, Craig tells Tweek they have to publicly breakup so that way they’ll be left alone. When the time comes, Tweek takes it to another level, suggesting that Craig was seeing someone else. It's a moving display of vulnerability by Tweek. It actually brings everyone down as the heartbreak resonates with the town. The situation may have been faked, but the emotions are real.

#13: Cartman Saves Kyle

At the Pentagon, government officials open a portal to Imaginationland but ManBearPig comes through it and begins wreaking havoc. In order to save everyone from the monster, the portal is reversed but not before ManBearPig manages to grab Kyle. The resultant energy released from the portal shocks Kyle and leaves him unconscious and dying. Despite efforts to revive him, it looks like he’s gone for good. Cartman, however, refuses to accept Kyle’s fate and in desperation tries to revive him. Just when it seems all hope is lost, Kyle regains consciousness. You can argue Cartman did it for selfish reasons but he did break down at the thought of losing Kyle.

#12: Satan’s Sacrifice

ManBearPig is real and he’s a danger to everyone. Kyle, Cartman, Kenny and Al Gore are able to convince Satan to stop ManBearPig. The two face off in an intense battle. Sadly, Satan is overpowered and left for dead. Before passing on, he admits his regret for not being able to stop ManBearPig. It’s quite shocking to see him go because it’s hard to imagine that he could die but as he informs Kyle, everyone dies. Even though his last moments were painful to watch, at least he ascended into heaven and is in a better place.

#11: Chad’s Breakdown

Cartman gets sent to a weight-loss camp and he’s not happy about it. It’s not long before he’s able to take advantage and start exploiting his fellow campers for his personal profit. The other kids are earnestly trying to make a positive change in their lives in order to be healthy. Eric comes with a plan to sneak in sweets to the camp so he can sell sweets to the others. Chad is in tears because he wants to stop eating junk food but can’t help himself. Cartman’s solution is to sell Chad a chocolate bar, not caring in the slightest about Chad’s pain.

#10: Beautiful Sadness

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

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 girls Photoshopping 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 disheartening.

#8: The Mountain Lion’s Death

“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 Antichrist. 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

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 preschoolers 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 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

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

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 substance use, 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 has a hard time at school and is 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, as we mentioned earlier, we see Kenny work tirelessly at City Wok, all to save up enough money to buy his sister a doll.

#3: Chef’s Death

When Isaac Hayes left the show after his Scientology entourage allegedly made a statement on his behalf following health issues, 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 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”

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’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.