The Decade’s Top 10 Pop Star Guest Appearances On ‘The Simpsons’

Twenty-one seasons in, The Simpsons continues to shine as a beacon of smart, funny TV. But it is also one of our favorite cultural fun-house mirrors, and we’d be remiss if we didn’t spend a moment looking back on the decade of pop that was through the prism that is America’s best dysfunctional animated family.

As we usher in 2010, we share our Top 10 picks for the best pop star appearances on The Simpsons over the last ten years (with “pop” being v-e-r-y loosely defined in order to accommodate our faves). Our list is in chronological order, making it all the easier to see how music—and the show—evolved through the 00s (starting with bubblegum pop, ending with edgier acts). Is anyone surprised that Bart, Homer, Marge Lisa and the gang have had longer careers than some of their guests?

Britney Spears – “The Mansion Family” (2000)


(Starts at 1:25.) Britney Spears appeared in a cameo as herself during the height of her fame, donned in her gym class couture “Baby… One More Time” garb. Although Brit never made another trip to Springfield, Maggie picked up a few of her tricks over the years.

‘N Sync – “New Kids on the Blecch” (2001)

Justin Timberlake’s long since left his boy-band years behind, which means he’s waaaay overdue for another appearance on the show (and given more to do than just say “word”). If only he could find the time between SNL digital shorts.

Blink 182 – “Barting Over” (2003)

Blink’s cameo was pretty brief, but there’s truly no one better to cast as Tony Hawk’s house band than the (reunited) pop-punk trio.

“Weird Al” Yankovic – Three Gays of the Condo (2003)

“Weird Al” not only provides a Simpson-ized take on “Jack and Diane,” but continues his song well into the credits. Can Weird Al move permanently to Springfield? He’d surely fit in with the rest of the locals.

50 Cent – “Pranksta Rap” (2005)

Fiddy gives aspiring rapper Bart some good advice – but only because he thinks it counts as community service.

Fantasia – “A Star is Torn” (2005)

Fantasia (the only musician on this list who didn’t appear as herself) plays a finalist in a singing competition, but in this version, she doesn’t win. Fantasia’s the only Idol personality to make a guest appearance on the show other than Simon Cowell. What are you waiting for, Carrie Underwood? An invitation?

White Stripes – “Jazzy and the Pussycats” (2006)

(Starts at :25.) In this episode, budding drummer Bart runs directly into the White Stripes—literally. A great homage to the Michel Gondry-directed video “Hardest Button to Button.”

Ludacris – “You Kent Always Say What You Want” (2007)

Ludacris appeared as himself appearing as a bottle of toothpaste in a commercial. Hey, he handled this gig better than his role in Gamer. (Apparently there aren’t enough Ludacris fans still out there, since this is the best quality vid we could find uploaded on the net.)

Green Day – The Simpsons Movie (2007)

Green Day kicked off The Simpsons Movie by playing a show for the citizens of Springfield—and then sinking à la the Titanic atop a barge. That’s what you get for trying to bring up the environment, you do-gooding rockstars!

Fall Out Boy – “Lisa the Drama Queen” (2008)

The emo-pop quartet’s name is a direct reference to Radioactive Man’s sidekick, and there’s no better way to repay the show that gave them their moniker than by covering The Simpsons‘ theme song. Pete, Patrick and the gang weren’t Simpson-ized, but the episode centered around the concept of folie à deux, which (not) coincidentally was the title of FOB’s album at the time.

Aspiring stars of the 2010s, take note: even as it heads toward 30, this show is one of our biggest public stages. If you can’t land yourself an appearance in Springfield, you haven’t made it.

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