16. Johnny Cash
Homer’s gorging of Guatemalan insanity peppers caused his digestive system to feel a huge ring of fire in “El Viaje Misteriose de Nuestro Jomer.” But it was Johnny Cash’s smoothly voiced coyote that helped guide Simpson to safety. Even though it didn’t have Cash singing or appearing as himself, his appearance easily walked the line into the best of yellow guest voice acting.
15. Hank Williams Jr.
The country music icon lent his voice to the Canyonero theme song from “The Last Temptation of Krust.” Even if you’re staunchly against SUV’s, it’s hard to deny Williams’s hearty Canyonero endorsement of “12 yards long, 2 lanes wide, 65 tons of American pride!” Yeehaw!
14. Tito Puente
It was a shame when Springfield Elementary lost their jazz program funding in “Who Shot Mr. Burns? (Part One)” But Tito Puente got his fiery revenge in the sultry salsa anthem titled “Señor Burns.” It was ultimately Maggie who gunned down Burns, but Puente’s electric brass anthem against “El Diablo con dinero” shot an electric bullet straight into Springfield’s musical heart.
13. Peter Frampton
“Frampton Comes Alive” hit the world like a cannonball upon its release in 1976, but the legendary rocker didn’t hit full fame until he appeared as a festival headliner in “Homerpalooza.” Frampton may not have loved Homer’s obnoxious ways, but his hilarious cameo made Simpsons fans want to laugh with the guitarist all night and day.
12. Barry White
The best musical guest stars are those who give a performance but also interact with the Springfield residents. And Barry White delivered fully in “Whacking Day” with his colorful rendition of his hit “Can’t Get Enough of Your Love, Babe.” Using White’s powerful vibratos, Lisa and Bart guide the town’s snakes to safety, as White humorously adds, “I love the sexy slither of a lady snake.” Bizarre and self-deprecating, White’s appearance was a perfect embodiment of that surreal factor that made the series so great.
11. The Smashing Pumpkins
One of the most popular acts of the 1990s, the Smashing Pumpkins were the golden fruit of the recording industry when they guest starred in “Homerpalooza.” Billy Corgan’s casual and friendly appearance made Homer smile politely and become less wary of Gen-Xers. Despite all The Simpsons funny rage, the Smashing Pumpkins by no means felt comically caged.
Notorious for their global philanthropy efforts, it would seem odd that global rockers U2 would ever care about a small town’s Sanitation Commissioner election. But Bono and crew graciously lent Homer a hand in “Trash of the Titans,” helping the inadequately prepared Simpson triumph over the incumbent Ray Patterson. Unlike Homer who still hasn’t found the landfill he was looking for, U2’s reputation was far from trashed after appearing in this later episode.
Environmentally conscious rockers R.E.M. were the toast of the 1990’s/early 200’s alternative era. And even though it felt like the end of the world for Homer when his favorite bar went modern in “Homer the Moe,” R.E.M.’s fun and self-deprecating performance seemed like a whole new Simpsons musical beginning.
8. Tony Bennett
Bennett wasn’t actually animated in “Dancin’ Homer,” but when his voice began narrating the Homer-baseball montage, you knew he was the only crooner whose voice could make animation come so alive. Bennett was one of the earliest musical guest stars of the series, and just as he continues to perform into old age, his montage voiceover remains a timeless class act.
7. The Ramones
There’s no other group on the planet who could piss off Mr. Burns so much that he orders to kill the Rolling Stones quite like punk icons The Ramones. Invited to play at Mr. Burns’ birthday party in “Rosebud,” the Ramones give a big F-you to the energy tycoon. It was a brief appearance, but one so irreverent and hilarious that the anti-institution Ramones become happy mainstays of the Springfield establishment.
6. Red Hot Chili Peppers
Wearing nothing but briefs was an early on-stage antic for the Red Hot Chili Peppers. But their funny sensibilities were fully clothed in “Krusty Gets Cancelled.” Invited to play at Krusty’s comeback special, the California rockers graciously agree to family friendly changes proposed by the clown. Flea mistakenly animated Flea playing a guitar instead of bass, but Anthony Kiedis and crew just consider that error water Under the Bridge.
5. The Who
Legendary 1960’s rockers and passionate area code activists, it’s surprising that it took so long to get The Who to appear on the show. But the where’s and when’s of their appearances were non-important, as The Who drove a magic bus full of hilarity straight into Springfield. Homer was blindsided as his fat, dumb hardball efforts pushed everyone on his side of the trash wall out of town, ensuring that the band and residents of Springfield wouldn’t be fooled by his shenanigans again.
4. Mick Jagger and Keith Richards
Homer has held many envious career positions over the course of the series, but up until “How I Spent My Strummer Vacation,” rock star wasn’t one of them. But the charming, high-powered Mick Jagger and Keith Richards of The Rolling Stones helped start Homer’s dreams up. But Homer’s lust for fame and stardom squashed sympathy he had with the devilish rockers. Even amongst the likes of this episode’s other guest stars like Tom Petty, Elvis Costello and Lenny Kravitz, Jagger and Richards are the ones who truly keep the laughs rolling.
In a season full of classic episodes, “Flaming Moe’s” easily ranks among the best. But the episode wouldn’t have reached full funny capacity without the appearance of 70s and 80s era rockers Aerosmith. The band was the first rock group to appear together on the series, ensuring that many bands after them would have the opportunity to dream on in a Simpsons’ guest role.
2. The Beatles
They didn’t appear together, and John Lennon had passed away before the The Simpsons even came to air. But it is incredibly impressive that the show was able to get all three living Beatles at that time for guest roles. Marge’ painting fascination with Ringo Starr in “Brush with Greatness,” was bizarre yet hilarious. Homer’s run in with George Harrison in “Homer’s Barbershop Quartet” was self-referential and clever. And Paul McCartney’s non-animal culinary advice in “Lisa the Vegetarian” was a well cooked, endearing sentiment. These fab four members truly put on a fabulous show in The Simpsons.
1. Michael Jackson
His guest voiced as a character who impersonates Michael Jackson. And his supposed song was actually another singer, Kipp Lennon, mimicking Jackson’s voice in character as the Jackson impersonator. Like Jackson himself, this whole guest-voicing scenario was incredibly bizarre in “Stark Raving Dad.” But Jackson’s appearance happened right at the turn of the show’s golden years, where they evolved from just a crude, animated sitcom to something much more surreal and magical. Without Michael Jackson singing his way along as Leon Kompowsky, The Simpsons’ golden years wouldn’t nearly have been as thrilling.