South Park prides itself on being offensive, confronting, and going to dark places. Of course, it does this better than most adult animated shows, as South Park is, first and foremost, a satire of life and popular culture. But even amongst its own content, some episodes stand out in their darker tone above others.
They deal with extreme character choices, take a more serious stance on a specific subject matter, and discuss topics more confronting for a mainstream audience. Of course, it’s mostly all down with the classically cynical sense of humor South Park is known for. But sometimes, even South Park goes to darker places than expected.
10 "The Return of Chef" - Season 10, Episode 1 (2006)
After Issac Hayes left the show, the character of Chef had to be retired, and it’s as tragic a retirement if there ever was one. Chef returns to South Park after spending some time traveling with the Super Adventure Club. The boys find that Chef has changed dramatically, talking weirdly and expressing unsavory desires for them.
They go to the Super Adventure Club, only for them to reveal they’ve brainwashed him to follow their evil practices. When they try to save him, Chef ends up being struck by lightning, set on fire, jagged by rocks, and mauled by mountain lions. It’s a legitimately sad and horrifying end for such a beloved character to go out on.
9 "Woodland Critter Christmas" - Season 8, Episode 14 (2004)
Out of all the Christmas specials South Park has produced over the years, this one is easily their darkest and best yet. A few days before Christmas, Stan finds a group of talking woodland critters making a tree. They’re excited because Porcupiney the Porcupine is going to give birth to their savior. But what begins as wholesome fun soon descends into hell – especially since the critters are actually Satan worshippers.
They discover Kyle is the perfect vessel to ingest the Anti-Christ’s spirit and usher in a new era of darkness. Now Stan must stop them with the help of a group of orphaned cubs and a gun-toting Santa Claus. Not a conventional Christmas by any means.
8 "Britney’s New Look" - Season 12, Episode 2 (2008)
Britney’s New Look is the rare episode revolving around a celebrity that seems to take pity on them rather than mock them. A new piece about Britney Spears appears to be hitting the airwaves of South Park every day, and Stan & Kyle decide to get a photo of her to sell for cash.
But the more time they spend with her, the more they realize she’s desperate to escape the press. As the episode continues, Britney is pushed to the limit, literally blowing half her head off, and eventually photographed to death by the paparazzi as part of an ancient sacrifice.
7 "Butter’s Very Own Episode" - Season 5, Episode 14 (2001)
Butters’ parents have shown themselves as terrible people before, but Butters’ Very Own Episode brought them down to a new low. After discovering her husband’s seeming infidelity, Butter’s mom tries to drown him inside a car in the river in grief-induced hysteria.
Once she calms down and realizes what she’s done, the two lie to the press and claim their son was abducted. Little do they know that Butters survived and is borderline oblivious to his parents’ terrible behavior. Butters seems to have a knack for falling into traumatizing situations that shatter his innocence.
6 "Kenny Dies" – Season 5, Episode 13 (2001)
Until this point in the series, Kenny would die in almost every episode and return the following week without explanation. But in Kenny Dies, he is faced with a terminal illness and is played chiefly dead straight.
The rest of the boys have their distinct reactions – Kyle stays in the hospital to be by Kenny’s side, Stan refuses to see him out of grief, and Cartman decides to profit off it to lift a ban on stem cell research. Thankfully, Kenny came back a year later and has remained alive since.
5 "Stanley’s Cup" – Season 10, Episode 14 (2006)
After Stan’s bike is towed away, he’s stuck coaching a hockey team for little kids. One of the kids, Nelson, has a terminal illness, and only a win against the Detroit Red Wings can be enough to save his life. Unfortunately, the team is not precisely well-trained for playing in the big leagues.
Of course, audiences expect sports stories like Stanley’s Cup to end with the team winning and the illness being beaten or mitigated. But instead, it ends on a decidedly cruel note that may be uplifting for one team but is utterly devastating for another.
4 "Cartman Joins NAMBLA" – Season 4, Episode 5 (2000)
In a characteristic display of narcissism, Cartman decides his regular friends aren’t “adult” enough for him anymore. So he decides to find some adult friends on the internet, only to eventually run afoul of a group called NAMBLA. The group invites the boys to hang out at a hotel, but it’s apparent the members don’t exactly have their best interests at heart.
Meanwhile, Kenny finds out that his mom and dad are trying for another baby, and he tries everything he can to ensure that the baby isn’t conceived. The two plots collide in a cavalcade involving Marlon Brando lookalikes, a Scooby-Doo-esque chase through the hotel, and Kenny’s dad needing a hot bath.
3 "Crack Baby Athletic Association" – Season 15, Episode 5 (2011)
In a typically evil Cartman scheme, he, Butters, Craig, and Clyde have decided to form the Crack Baby Athletic Association. In this new company, they film drug-addicted babies fighting each other and post their videos online. Soon they become ridiculously popular, as they receive offers from EA Sports to make a video game out of them.
While horrified by Cartman’s actions, Kyle finds himself directly participating in the schemes. Unfortunately, the happy ending the boys receive still doesn’t entirely diminish the shock that they’ve used babies’ drug addictions for profit.
2 "HumancentiPad" – Season 15, Episode 1 (2011)
When it comes to traumatizing events faced by the boys, Kyle is only second to Kenny in exposure. But no episode has put Kyle through a worse predicament than in HumancentiPad. One day, he downloads his latest iTunes update but makes a near-fatal mistake when he does not read the terms and conditions.
Once Steve Jobs and his Apple agents capture him, he is forced into a horrific punishment right out of The Human Centipede. In the end, the only happy note the episode ends on is when Cartman is struck by lightning after angering God.
1 "Scott Tenorman Must Die" – Season 5, Episode 4 (2001)
Scott Tenorman Must Die marked a turning point in Cartman’s character from a racist bully to a borderline psychotic supervillain disguised as a kid. In this episode, he finds himself a target of pranking and bullying by teenage punk Scott Tenorman. No matter what Cartman tries to do for payback, Scott always seems to be one step ahead.
In perhaps Cartman’s most evil action to date, he decides to take a page out of Titus Andronicus’ book. Cartman has Scott’s parents killed, makes them into chili, and feeds it to a horrified Scott for a final act of revenge.