The cultural impact of The Simpsons is immeasurable, as you can tell from checking out Joey "Sideshow Joe" DeGroot's list on the number of bands that named songs (or themselves) after references to the animated classic. Celebrities of all stripes realize the kind of power that such a program packs so they'll readily appear as guest stars. The number of musical guests in the history of The Simpsons is huge, but we've whittled it down to nine of the best in honor of the current marathon of every episode currently happening on FXX.
Ron Taylor on "Moanin' Lisa" (Season 1)
The first musical guest in the history of The Simpsons is far from the flashiest, but Ron Taylor voiced one of the most renowned side characters in the history of the show: Bleeding Gums Murphy. Lisa meets the bluesy saxophone player when she sinks into an epic funk unfit for a girl of her age. She bumps into Murphy on the Springfield Bridge and the pair commiserates over the blues and their mutual instrument of choice. Lisa channels her angst into the "Moanin' Lisa Blues," which later appeared more fully decorated on The Simpsons Sing The Blues album.
Michael Jackson on "Do The Bartman"
Matt Groenig must've known he had hit gold when Michael Jackson, one of the biggest performers of all time came to him looking for a role. The vocalist wasn't able to sing in an episode due to contractual obligations but he helped pen "Do The Bartman," a track that would appear first on The Simpsons Sing The Blues and rise to no. 11 on the Billboard Hot 100. Groenig kept the secret of Jackson's involvement until many years later to keep the prince of pop safe from litigation.
Tito Puente on "Who Shot Mr. Burns?" Eps. 1 + 2 (Seasons 6/7)
Perhaps the most famous episode in the history of the series featured one of its less mainstream guest stars. Legendary timbales player Tito Puente lent his rhythmic skills to "Señor Burns," a Latin American track that set the tone for the almost-murder that would later occur. This remains one of the funniest songs in the Simpsons catalogue: "Please die and fry in hell/you robbin' rich old wretch."
"Homerpalooza" (Season 7)
Homer heads to Hullabalooza and mingles with the stars, who came out in en masse for the effort. The Smashing Pumpkins, Cypress Hill, Peter Frampton and Sonic Youth all make appearances, performing for a self-mocking festival audience. Sonic Youth would contribute an original recording for the episode, coming up with their own glitch-ridden version of the show's classic outro music. Rumor has it Neil Young, Bob Dylan and Pearl Jam were all sought out for roles but never responded.
"How I Spent My Strummer Vacation" (Season 14)
The biggest episode in the history of The Simpsons when it comes to musical guests. Homer and some familiar Springfieldians head to Rock 'n' Roll fantasy camp, where they rub elbows with Elvis Costello, Lenny Kravitz, Tom Petty, Brian Setzer, plus Keith Richards and Mick Jagger of The Rolling Stones. Ultimately the episode can't quite live up to the potential of its guest stars but it was certainly an ambitious attempt.
Weird Al Yankovic on "Three Gays of The Condo"
Weird Al has the perfect shtick for appearing on The Simpsons so it's sensible enough that he's made multiple appearances over the years. His first is still the best however, when Marge hires him in an effort to win back Homer. Weird Al delivers "Homer and Marge," a play off of John Mellencamp's "Jack and Diane." The best verses occur after the episode however as the performer provides live commentary of the credit sequence through his song.
Sir Mix-A-Lot on "Treehouse of Horrow XVII" (Season 18)
It's interesting to note that the classic Treehouse of Horror Halloween episodes have only ever hosted musical guests twice. The first was British vocalist Paul Anka way back during "Treehouse of Horror VI," but second guest Sir Mix-a-Lot takes the cake, somewhat literally. In a mini-episode titled "Married to The Blob," Homer's eating habits take advantage of him and he grows larger and larger, devouring part of Springfield in the process. The rapper spoofs his own "Baby's Got Back" with "Baby Likes Fat."
Green Day on The Simpsons Movie
Playing a rock 'n' roll version of The Simpsons theme song would be just a little too easy of a way to crack onto this list. Green Day sticks around however, delivering an environmental protection speech while performing on a barge in Lake Springfield. This induces the ire of the crowd, which sinks the boat with a barrage of garbage, setting the later pollution plot in motion. During the band members' funerals, the organist at the First Church of Springfield plays "American Idiot."
Rob Halford on "Steal This Episode" (Season 25)
Homer is holed up in the Swedish embassy when the FBI comes after him for film piracy. In a reference to the siege on Panamanian dictator Manuel Noriega, the agency attempts to force Homer out by playing "death metal" in the form of Judas Priest and a revised version of its classic "Breaking The Law." The episode brought the wrath of metal fans however, who insisted that Judas Priest was not in fact death metal. The show apologized for its gaffe by having Bart repeat "Judas Priest is not death metal" on the blackboard in a later episode.