Kid Rock Oh, that Homer. In an episode that aired just after the turn of the millennium, Homer, saddened to learn that he may only have four more years to live, meets up with some rowdy Spring Breakers during a trip to Florida to “recover.” There, all fears of mortality aside, Homer attends that undisputed king of white-dude rap-metal’s concert.
50 Cent On a 2005 episode called “Pranksta Rap,” in which Bart gets himself into trouble at hip-hop show, he runs into Fitty. The uninspiring pop rapper, who’s seen his share of juvenile delinquent behavior, waxes philosophical and advises the pint-size troublemaker to stay in school.
Sting Once the driving force behind the Police, solo Sting has always been a bit more middlebrow, adult-contemporary than we’d like. But we sure didn’t mind seeing the hilariously heroic rocker (or whatever he is now) save Bart after the boy falls into a well.
James Taylor He’s seen fire and he’s seen rain, and our moms love him. But since the ’60s, his music has begun to attract the scent of, say, cheese that’s been aged too long. On a futuristic episode of The Simpsons, Taylor — who has been elected president — serenades Homer and Buzz Aldrin aboard an imperiled spacecraft. (Watch the clip here.)
Britney Spears Way back in January 2000 (yes, she has been famous for over a decade now), Britney Spears popped up on The Simpsons to present an award to the city’s oldest man, Cornelius Chapman. Sure, she may have subsequently killed him with her kiss, but at least he died happy.
‘N Sync Before he broke free from the pack for a surprisingly interesting solo career, Britney’s then-beau Justin Timberlake was just another member of pubescent boy band ‘N Sync. In retrospect, we should have known that the group’s appearance on an episode meant to send up their whole embarrassing genre was a sign of good things to come.
The Dixie Chicks Listen, we’ll never stop being happy that the Dixie Chicks were brave enough to stand up against George W. Bush. But nothing could make us love their pop-country balladry. Still, they’re an essential part of the plot in an episode of the show that features Springfield’s local fallen country star, Lurleen Lumpkin.
Coldplay Earlier this year, The Simpsons celebrated their 20th anniversary on air by bestowing upon Homer a million-dollar lottery windfall. We’re kind of disappointed that he spent his money by choosing Coldplay, of all bands, to serenade his his family. But at least Chris Martin, et. al., seemed to have fun recording for the show.
Smashing Pumpkins The year was 1996. Alt-rock was at its mid-decade height. And The Simpsons paid tribute to youth culture with their classic “Homerpalooza” episode. To be fair, the show aired long before the Smashing Pumpkins (and, most notably, their moody, self-important main man, Billy Corgan) started sucking. But whenever we start to really hate on the band, we need only think of this guest appearance to remember why it was we liked them so much back in junior high.
Metallica While they had some classic singles back in the day, we’ve been pissed at Metallica ever since they led the charge against Napster (as though they weren’t already making enough money on album sales). But at least they had the sense of humor to appear on The Simpsons and make light of their own asshole behavior, in a clip where they cruelly ditch mega-fan Otto for a less obvious supporter.