10 Saddest ‘South Park’ Episodes of All Time, Ranked

South Park is more than just a hilarious piece of adult animation, but one of the most emotionally, politically, and philosophically complex works of television released in the 21st century. Although it is the raunchy humor that has helped Trey Parker and Matt Stone create such a transgressive feat in storytelling, South Park often taps into real emotions based on the connection that the audience has formed with the characters over an extended period of time; watching Cartman, Kenny, Kyle, Stan, and Butters grow up to deal with the world’s problems can be oddly touching, especially for those that had been watching since the beginning.
Although it has never been a series that takes itself too seriously, South Park has the ability to go into surprisingly dark and devastating places. It’s a credit to both Parker and Stone that they were willing to create an active series that did not simply retain the status quo. Here are the ten saddest South Park episodes of all time, ranked.

- Release Date
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August 13, 1997
- Network
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Comedy Central
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Liane Cartman / Wendy Testaburger / Mrs. Crabtree (voice)
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Kyle Broflovski / Kenny McCormick (voice)
10
“The City Part of Town”
Season 19, Episode 3 (2015)
“The City Part of Town” was a surprisingly ambitious piece of economic satire that examined the evils of corporatization and gentrification. Although Kenny’s family has always been very poor, he decides to get a job as part of the child labor force working for the restaurant City Wok, which is owned by Mr. Kim. Unfortunately, the restaurant is shut down by PC Principal, which makes it impossible for Kenny to buy a present for his sister.
Kenny is often one of the most empathetic characters on South Park, as he does not share the hateful views of Cartman, and rarely does anything to betray his friends. Although Kenny’s family life is often tormented, the fact that he was not able to bridge a thoughtful connection with his sister makes “The City Part of Town” a particularly hard episode to watch.
9
“Free Willzyx”
Season 9, Episode 13 (2005)
Although it started out as a broader parody of the recent hit family film Free Willy, the episode “Free Willzyk” takes an unexpectedly emotional turn when it highlights the treatment of animals that are held for public entertainment in places like SeaWorld. Although employees at an amusement park manage to convince Stan, Kyle, Cartman, Kenny, and Butters that the massive orca Jamba wants to be taken back to his home on the moon, they ultimately decide to try and send him free.
“Free Willzyk” examines how animals have been deprived of their livelihood for the sake of being put on display, and how ignorant their captors often are about where they come from. It’s particularly sad because it shows the boys the very dark, cruel, and selfish world that they are about to grow up in as they learn more about global events..
8
“Bloody Mary”
Season 9, Episode 14 (2005)
Although it attracted a significant amount of controversy due to the depiction of some Christian characters and imagery, “Bloody Mary” is a very dark episode about the nature of addiction. After Stan realizes that his father, Randy, has become an alcoholic, he watches him try to get rehabilitation by learning from Christian scripture. Unfortunately, Randy manages to take all the wrong lessons, and only exacerbates the situation for his family.
Although he’s not always necessarily been the most likable character on South Park, it’s hard to not feel at least somewhat sympathetic for Randy, as he does not have the proper resources to cope with his issues with drinking. It’s even more devastating for Stan, who is once again forced to suffer in silence as his family falls apart; the relationship between father and son would become even more strained in subsequent seasons.
7
“Help, My Teenager Hates Me!”
Season 25, Episode 5 (2022)
“Help, My Teenager Hates Me!” is a satirical episode about adolescence that examines the ways in which teenagers tend to drift apart from their parents. Kyle, Cartman, Stan, and Kenny want to play Airsoft, but are forced to team up with a group of moody teenagers in order to participate; although initially they enjoy hanging out with a group of teens that are much older than them, they find that their new friends begin to show less interest in the activity, making it harder for them to pull off a victory.
The episode was a surprisingly nuanced examination of a generational divide, in which teenagers show such resistance to making friends that they destroy the opportunities that are in front of them. The message is strengthened by the moments that include Randy and Gerard, who recognize that their own children will be growing into teenagers at some point.
6
“You Have 0 Friends”
Season 14, Episode 4 (2010)
“You Have 0 Friends” was a surprisingly complex breakdown of the reality behind internet bullying on social networking platforms like Facebook, and was coincidentally released only a few months before the Mark Zuckerberg biopic The Social Network was hailed as one of the best drama films of the 21st century. The episode shows Stan being reluctantly forced to join Facebook, and how he begins to lose all of his digital friends after he becomes associated with the kid known as “Kip,” who everyone else in school considered to be a loser.
“You Have 0 Friends” shows the severe mental health issues that can result from constant social media usage, and how it can be easier to post cruel comments from behind a keyboard. Although Stan is often more mature than any of his other classmates, the episode indicates that even the intelligent kids in South Park may be upset based on the way that they are treated online.
5
“The Return of Chef”
Season 10, Episode 1 (2006)
“The Return of Chef” is a very controversial episode of South Park that resulted in a real-life feud between Parker, Stone, and the actor Isaac Hayes, who had voiced the character of Chef. Hayes, a Scientologist, had left the show after an episode in the previous season mocked the Church of Scientology, meaning that the character of Chef could not be used, and would be killed off in South Park itself.
“The Return of Chef” turns Chef into a villain who has been brainwashed by the Church of Scientology and forced to join the evil Super Adventure Club group. It’s a particularly heartbreaking episode for Kenny, Stan, Kyle, and Cartman, as they are forced to accept that Chef is no longer the same man that they looked up to, and will never be able to be an active part of their lives ever again.
4
“The Poor Kid”
Season 15, Episode 14 (2011)
“The Poor Kid” is a surprisingly ambitious episode that deals with children living in abusive households, but still manages to have some of the trademark South Park humor thanks to a storyline that allows the boys to use their superhero identities. Kenny and his sister are forced to join a foster kid program after it is discovered that their parents have a meth lab in their home; although Cartman had always enjoyed making fun of Kenny for being poor, he begins to develop a genuine sense of sadness when he realizes that he’s not there to mock anymore.
It’s oddly quite gripping to see how Kenny is treated throughout the episode, but even more surprising is the fact that it is actually able to turn Cartman into a somewhat sympathetic character, which only occasionally occurs throughout the entire history of South Park.
3
“Raisins”
Season 7, Episode 14 (2003)
“Raisins” made a pretty significant change to the overall story arc of South Park, as it featured the first major breakup between Stan and his girlfriend, Wendy. After Stan realizes that Wendy isn’t going to simply forgive him and move on, he begins suffering from serious feelings of depression. Stan’s friends try to cheer him up by taking him to the restaurant known as “Raisins,” but the situation grows more complicated than any of them intended when Butters falls in love with a waitress that just uses him for money.
“Raisins” did a great job at showing what it is like to be young and in love, and how a character like Stan would begin to think poorly of himself after feeling rejected by Wendy. Most uncomfortable is that by the end, Stan realizes that the only catharsis he can get is by insulting Wendy and her new boyfriend.
2
“You’re Getting Old”
Season 15, Episode 7 (2011)
“You’re Getting Old” is one of the most profound episodes of South Park, as it genuinely captures what it is like to deal with feelings of depression. After Stan celebrates his birthday, he finds that he is no longer able to enjoy the things in life that he once did; his negative attitude forms a barrier with his friends, who begin to avoid him because of his increasingly negative attitude.
“You’re Getting Old” was very authentic in how it dealt with mental health, particularly in how it visualized the new ways in which Stan viewed the world. Although Stan was ultimately able to reconnect with Kenny, Kyle, Cartman, and Butters, the episode does not imply that his depression has been cured; unfortunately, this is an issue that he will be forced to deal with for the rest of his life.
1
“Kenny Dies”
Season 5, Episode 13 (2001)
“Kenny Dies” paid off a long-running joke in South Park in which Kenny would be killed in some very dramatic way at some point in an episode. Although he had always managed to come back, “Kenny Dies” shows what happens when Kenny is actually diagnosed with a terminal illness, forcing Kyle, Cartman, and Stan to cope with the fact that their friend will actually die.
“Kenny Dies” actually had serious consequences for South Park, as Kenny was absent from the show for nearly an entire year before he made his return in the holiday-themed episode “Red Sleigh Down.” Even if it was eventually retconned, it’s a very touching episode that shows that the boys are capable of being quite emotional and vulnerable, even if they often like to mask any signs of sensitivity when they are out in public.