For more than 20 years now, South Park has been making fun of everything from politics to the economy. One of the show’s most common targets is celebrities. The great thing about Trey Parker and Matt Stone’s humor is that they usually lampoon people and institutions who could do with being taking down a peg, so it makes sense that the rich and famous are one of their favorite subjects.

They particularly enjoy taking aim at celebrities who are mean-spirited or arrogant or elitist in real life, because they’re fun to make fun of – and, on some level, they deserve it. But sometimes, the show takes things a step too far.

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Funniest: Russell Crowe

russell-crowe-south-park

“Makin’ movies, makin’ songs, ‘n fightin’ ‘round the world!” In the season 6 episode “The New Terrance and Phillip Movie Trailer,” the boys have to sit through an episode of Russell Crowe’s reality series in order to see the trailer for the upcoming Terrance and Phillip movie. (Remember those dark, dark days before YouTube?)

Crowe is a notorious diva in real life, and he also gets into a lot of fights due to his bad temper, so Trey Parker and Matt Stone gave him a fictional reality TV show in which he brags about himself, sings a bunch of terrible songs, and beats up anyone who looks at him.

Went too far: Oprah Winfrey

Towlie and Oprah on South Park

In a satire of the Million Little Pieces debacle, the South Park episode “A Million Little Fibers” revolves around Towelie writing a memoir and pretending it was written by a human, shocking readers when they discover that he’s really a towel. Meanwhile, Oprah Winfrey’s vagina and anus conspire against her.

The A-plot was a little undercooked, but the B-plot was just outright unfunny. Trey Parker and Matt Stone have since admitted that “A Million Little Fibers” is one of their worst episodes, saying that the story was a “hat on top of a hat,” meaning it was weirdness on top of weirdness.

Funniest: The Jonas Brothers

South Park’s season 13 premiere episode, “The Ring,” is all about the media craze surrounding the Jonas Brothers. Kenny’s girlfriend is a fan of the band, and it leads him to uncover a conspiracy that Disney is secretly using the Jonas Brothers to sell sex to girls.

Although the subject matter is very uncomfortable – this is South Park, after all – the episode works surprisingly well. It becomes particularly hilarious when Mickey Mouse shows up to beat the crap out of the Jonas Brothers to keep them in line. When the episode aired, the band’s publicist barred interviewers from asking them about it.

Went too far: Christopher Reeve

In the season 7 episode “Krazy Kripples,” Christopher Reeve comes to town and the residents of South Park become obsessed with him. They keep saying that he’s “such an inspiration,” and Jimmy is mad that everyone missed his standup show to go and see Reeve’s appearance, repeatedly calling the Superman star “the super b******e.” All of this worked really well.

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But the episode took a step too far when it depicted Reeve actually sucking stem cells out of unborn fetuses. His battles with Gene Hackman, swapping their hero/villain roles from the Superman movies, are really funny, but the fetus scenes drag it down.

Funniest: Mel Gibson

“The Passion of the Jew,” South Park’s satirical response to Mel Gibson’s The Passion of the Christ is one of the show’s most incisive installments. Kyle watches the movie and feels guilty about the crucifixion of Christ, while Cartman starts a Passion of the Christ fan club that is basically a neo-Nazi movement.

Stan and Kenny watch the movie and see it for what it is – a gruesome, gory, violent slugfest; Stan even calls it “a snuff film” – so they travel up to Hollywood to get their money back from Gibson. Trey Parker and Matt Stone’s message is that a film made by such a wacky guy shouldn’t become the center of such fervent socioreligious discussion.

Went too far: Steven Spielberg & George Lucas

In a series of shocking parodies of movies like Deliverance, The Accused, and Boys Don’t Cry, South Park depicted Steven Spielberg and George Lucas attacking Indiana Jones in various settings and graphically assaulting him. This is supposed to be how Indy fans remember the fourth movie.

We can all agree that Kingdom of the Crystal Skull was a bad movie – and a lot of Indiana Jones fans felt betrayed – but this storyline was too disturbing to be funny. And comparing the disappointment of watching a bad sequel to the trauma of assault was just uncomfortable, because it trivializes the latter.

Funniest: Jennifer Lopez & Ben Affleck

Trey Parker and Matt Stone really didn’t hold back when they satirized Jennifer Lopez and Ben Affleck in the episode “Fat Butt and Pancake Head.” In the episode, Cartman manages to steal Lopez’s career (and her husband) with a hand puppet. He does a ventriloquist act at a cultural diversity event, and drives Kyle crazy by refusing to give up the act and taking it too far.

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When Lopez and Affleck come to town, the former is depicted as a shrill diva who thinks she’s above everyone else (which isn’t far off), while the latter falls in love with Cartman’s hand.

Went too far: Britney Spears

In one of South Park’s darkest installments, Britney Spears gets tired of the paparazzi constantly hassling her and blows her head off with a shotgun – which the press then terms her “new look.” In a harrowing parody of the classic Shirley Jackson short story “The Lottery,” it turns out that the media has been bullying Britney Spears in order to sacrifice her in America’s annual harvest.

It’s a smart satire of the harassment faced by celebrities, but it was also a little too shocking to be funny. The episode gets bonus points, though, for predicting that Miley Cyrus would be the next pop star to face brutal media scrutiny.

Funniest: Kanye West

Kanye West looking angry sitting in front of a talk show host in South Park.

The premise behind Kanye West’s appearance in South Park is simplistic, but incredibly effective. “Fishsticks” lampoons West’s delusions of grandeur and insistence that he’s a genius with the tale of Jimmy coming up with a joke that spreads across America like a wildfire – and West is the only one who doesn’t get it.

The episode ends with a hilariously autotuned (and surprisingly catchy) song called “Gay Fish,” a spoof of West’s track “Heartless.” After West infamously interrupted Taylor Swift’s acceptance speech at the 2009 MTV Video Music Awards ceremony, Comedy Central played this episode of South Park four times back-to-back.

Went too far: Steve Irwin

South Park Steve Irwin at Satan's Party

In one of South Park’s most controversial moments, Steve Irwin appeared at Satan’s Halloween party with a stingray sticking out of his chest. The show is known for its shock humor, but even by its usual standards, this joke is all kinds of wrong. For starters, it had only been a few weeks since Irwin’s death when this episode, “Hell on Earth 2006,” first aired.

It depicts his cause of death in a really graphic manner, and implies that he went to Hell. Irwin’s widow, Terri, worried that her kids might see the episode. It was just in bad taste. And what’s worse is that Irwin was a good guy; he wasn’t a deserving target like a lot of the celebrities that South Park spoofs.

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