Radiohead Hates Scott Tenorman (2001)
Season 5 highlight "Scott Tenorman Must Die" may be best remembered for its hilariously disturbing final scene, but the episode also featured a rare TV cameo by Radiohead themselves, who stop by Colorado after receiving some fan mail from Cartman. Even those who don't appreciate alternative rock must have enjoyed Thom Yorke exclaiming, "This poor kid has cancer! In his ass!"
The Cure for Barbra Streisand (1998)
"South Park" has skewered its fair share of musical artists, but it's hard to imagine anyone getting it worse than Barbra Streisand, who literally tortures the boys with her singing voice before morphing into a robotic "Mecha-Streisand" that destroys South Park. Meanwhile, the same episode portraying Cure frontman Robert Smith (he provided his own voice for the episode) as a superhero, capable of defeating evil without losing his dejected coolness. Before he walks off into the sunset, Kyle yells, "'Disintegration' is the best album ever!"
Kanye West Loves "Fish Sticks" (2009)
In "Fishsticks," Kanye West is the only person in the country who fails to see the humor in the funniest joke of all time. Parodying the rapper's healthy ego, he refuses to admit that he doesn't get the joke because he is a "genius."