The Simpsons' Top 11 Musical Guests

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When The Simpsons completes its last (contracted) season in 2014, it will have set staggering new broadcast records for longest running sitcom (over 550 episodes) and longest running prime time scripted TV series (25 seasons). These are all American records, of course, because the Japanese come hardcore.

The show has long passed the point where we could simply refer to it as that show where "an old drunk made humans out of his rabbit characters to pay off his gambling debts (RIP, Phil Hartman). The Simpsons' merchandising reach rivals that of KISS, it's introduced new words to our very language, and briefly gave us all a reason to watch Fox.

For Rocks Off's purposes, however, the show has also showcased a large number of old and new musical acts. Here are a few of our favorites.

We've tried, when possible, to present examples across the spectrum of the show's 23 seasons, and stuck (mostly) with acts who actually performed on the show. See Honorable Mentions at the end before leaving your indignant "What about George Harrison?" comments.

And before anyone complains about the quality of these clips, bear in mind that Fox is crazy about keeping Simpsons footage off the Interwebs. The better to increase DVD sales. Guess they're crazy... like a fox.

11. Tony Bennett, "Dancin' Homer" (Season 2)

The second season of the show was when you really got the sense The Simpsons was something special. And not just because the show was able to get Bennett to sing the theme song for Capitol City, where "people stop and scream hello."

10. Linda Ronstadt - "Mr. Plow" (Season 4)

One of Rocks Off's favorite episodes features the rivalry between Homer and Barney's respective snowplow ventures. Barney ups the stakes by getting Ronstadt to sing his theme song... and then romancing her. Song's at the 3:15 mark.

9. Barry White, "Whacking Day" (Season 4)

Another great one, from Homer's whacking dojo to Mayor Quimby's "pre-whacked" snakes to Galveston's own Barry White expressing his disgust at the holiday.

8. Red Hot Chili Peppers, "Krusty Gets Kancelled" (Season 4)

When the network pulls the plug on Krusty the Clown's show, he pulls in some heavy hitters for his comeback special (although he has a minor problem with some of RHCP's lyrics). On a side note, how pissed do you think John Frusciante was that the only Peppers' guitarist to be immortalized on The Simpsons was Arik Marshall? Better him than Jesse Tobias, we guess.

7. The Ramones, "Rosebud" (Season 5)

This might be our favorite musical guest ever, and special kudos for accurately capturing Joey's onstage movements. Mr. Burns' cultural ignorance is always hilarious, as well.

6. Robert Goulet, ""$pringfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling)" (Season 5)

Goulet always was great about poking fun at himself, from appearing on Police Squad and TV Funhouse to singing "Jingle Bells (Batman Smells)" at Bart's casino.

5. Tito Puente, "Who Shot Mr. Burns?" (Season 6)

We take it back: Puente might just edge the Ramones in this competition. He certainly wins for best original song, and on what has to be considered the high water mark for the series itself. "El diablo con dinero," indeed.

4. Paul Anka, "Treehouse of Horror VI" (Season 7)

This is (almost) enough to forgive "(You're) Having My Baby." And a special thanks to the Russians, for their blatant disregard for American copyright laws.

3. Various Artists, "Homerpalooza" (Season 7)

Eager to get in touch with his kids' musical tastes, Homer procures tickets for Hullabalooza. The inspired presence of Cypress Hill, Sonic Youth, and the Smashing Pumpkins distracts us from asking the obvious question: "Why the hell is Peter Frampton headlining?"

2. Hank Williams, Jr., "The Last Temptation of Krust" (Season 9)

Bocephus doesn't actually appear onscreen, but who else could they have gotten to sing the praises of the Canyonero, the truck that "smells like a steak and seats 35"? One can't help wonder, however, if he really knew what he was singing was meant as a parody.

1. The Moody Blues, "Viva Ned Flanders" (Season 10)

Rocks Off has great personal affection for the Moody Blues, for reasons propriety and libel laws forbid us from discussing further. While you're contemplating how much the writers of The Hangover ripped off this episode, enjoy MB flautist Ray Thomas brandishing a switchblade as he says, "I want fatty!"

Naturally, we couldn't list everybody. Here are the ones that didn't make the cut, for whatever reason made sense to Rocks Off after our seventh beer.


The Beatles: Ringo Starr, "Brush With Greatness" (Season 2); George Harrison, "Homer's Barbershop Quartet" (Season 5); Paul McCartney, "Lisa the Vegetarian" (Season 7)

Though The Simpsons is to be commended for getting all three surviving members (at the time) onto the show, they all appeared in separate episodes, and none of them actually performed any music (Apu, recall, sang "Sgt. Pepper's" in "Lisa the Vegetarian").

Michael Jackson, "Stark Raving Dad" (Season 3)

While the King of Pop did, it was finally revealed, give Leon Kompowsky his speaking voice, his singing was actually performed by Kipp Lennon.

Sting, "Radio Bart" (Season 3)

Rocks Off is an unabashed Sting fan (a subject for a later entry, perhaps), and here he does a nice job poking fun at his reputation as a joiner.

James Taylor, "Deep Space Homer" (Season 5)

We couldn't actually find a clip of Taylor singing, so here's Homer accidentally freeing the ants.

Simpsons Medical Marijuana Episode from John on Vimeo.

Phish, "Weekend at Burnsies" (Season 13)

One of our few latter-era favorites, mostly because of stoned Homer. Enjoy the Scorpion King preview.

Johnny Cash, "El Viaje Misterioso de Nuestro Jomer" (Season 8)

"In your face, space coyote!" If only the Man in Black had sung something, Rocks Off feels sure he'd have topped our list.

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