South Park creators Matt Stone and Trey Parker have spent more than two decades roasting everyone from politicians to pop culture figures. And with the long-running animated show kicking off its 26th — yes, 26th! — season Feb. 8 on Comedy Central, the two masterminds are unlikely to stop.

In the show’s quarter century, it’s delivered parodies of musicians, from the uncomfortable (Britney Spears quite literally losing her head) to the hilarious (Randy Marsh is Lorde?!?!), with some artists even lending their voices to join in the fun (Robert Smith of The Cure battled on Mecha-Streisand). To celebrate 25 years and counting of genius (and, well crudely genius) intersections with our world, Billboard picked out some of the show’s most memorable moments involving musicians, from gay fish denier Kanye West to Jennifer Lopez as a hand puppet to Justin Bieber as “the enemy.”

And though we’re sticking purely to the Comedy Central episodes in this list, we do want to acknowledge that the show has spawned a feature-length film and more made-for-TV movies in recent years for Paramount+. South Park: Bigger, Longer & Uncut arrived in June 1999, and gave fans an unforgettably dirty (and successful) soundtrack to pair with it. The set — featuring such earworms as “Kyle’s Mom’s a Bitch,” “Blame Canada,” “What Would Brian Boitano Do?” and “Uncle F—a” — debuted at No. 82 on the all-genre Billboard 200 on the chart dated July 10, 1999, and peaked at No. 28 weeks later; it remained on the tally for 11 weeks.

Relive the animated TV show’s musical mayhem — in no particular order — below.

https://www.billboard.com/lists/south-park-best-music-moments/