We Ranked The 20 Best Musical Guest Stars On ‘The Simpsons’

The Simpsons has had an amazing litany of guest stars appearing as themselves over the years. Tony Blair was on as a sitting prime minister. Notorious recluse Thomas Pynchon has made a couple of appearances (always wearing a bag over his head, of course). Plus, Bob Denver, also known as Gilligan himself. Along the way, a bunch of musicians have stopped by the show. More than 40 musicians/bands have made credited appearances on The Simpsons, sometimes on multiple occasions. Here’s a ranking of the top 20 cameos by musicians as themselves on the show, which doesn’t include folks like Johnny Cash, who voiced Space Coyote.

20. Katy Perry

Perry’s appearance on the show was a very unique one. In the episode “The Fight Before Christmas,” she appeared in her real, human form in a story that was a parody of The Muppets. The episode ends with a rather lewd joke involving Perry and Moe. She gets on the list for uniqueness more than anything else.

19. Tom Petty

Petty was part of the musician-heavy “How I Spent My Strummer Vacation,” alongside a couple other folks further up on this list, and also Lenny Kravitz and Brian Setzer, who didn’t make the cut. Petty loses his toe, much to his chagrin.

18. Lionel Richie

In a more recent episode of The Simpsons, Richie appears to sing a beer-centric version of “Say You, Say Me” that eventually devolves into every word being “beer.” He gets credit for committing to it, and for still sounding good even when just singing the word beer over and over.

17. Dixie Chicks

In an episode that sees the return of Lurleen Lumpkin, her deadbeat father returns, steals one of her songs, and tweaks it for the Dixie Chicks. The song becomes the Dixie Chicks’ ode to their love of country and Fox News, poking fun at their image as liberal rabble-rousers. They’re also given some funny lines, which they deliver adequately.

16. Tito Puente

Puente definitely had a big role in his couple of episodes, the two-parter about who shot Mr. Burns. He sang a song of revenge, and he punched a hole in a conga drum. However, in truth, he doesn’t even sing the song, but he’s still one of the more iconic musician guest appearances.

15. Ringo Starr

Ringo appeared way back in season two, making him one of the first huge guests the show ever had. A big fan of the show, perhaps Ringo’s appearance helped lead to other big cameos in future episodes. While “Brush with Greatness” has a lot of paintings of Ringo in it, he actually doesn’t get a ton to do in the episode. However, his impact was still notable, and he was still funny.

14. Sting

“Radio Bart” is a delightful episode, and Sting is a big reason for this. He gets to be part of the hit charity single “We’re Sending Our Love Down a Well,” which is eventually overtaken on the charts by “I Do Believe We’re Naked” by Funky See, Funky Do. He also leads the way in digging Bart out of the well. The fact that Sting had some acting experience (for example, the movie Dune) meant that he had more acting chops than some other musicians who have stopped by Springfield.

13. Michael Jackson

Look, Jackson’s appearance on The Simpsons is definitely, even still, the most significant musician appearance on the show. He did a ton of voiceover work, although he didn’t actually sing, instead having a guy named Kipp Lennon do the singing in order to “play a trick on his brothers.” But, in my opinion, this episode isn’t very funny. “Lisa, It’s Your Birthday” isn’t a great song, and Jackson doesn’t get many funny lines. All this being said, out of pure cultural impact, he needs to be on this list somewhere. Also, he wrote “Do the Bartman.”

Now, there may be those of you saying, “Hey, Michael Jackson didn’t play himself! He played a big, white mental patient who thought he was Michael Jackson.” This is technically true, but for all intents and purposes, he still plays himself. Throw an asterisk on it if you want, but it should count.

12. Elvis Costello

In the aforementioned episode with Tom Petty, Costello doesn’t say much, but he gets two very funny bits to do. One, when Homer takes his hat and glasses, he says, “My image!” Two, he takes Homer’s guitar, drives off, comes back, and says, “It came with a pick.” That’s all it takes to really make an impact in an episode.

11. Barry White

Let’s say you needed to drive a bunch of snakes into one area through the usage of deep, resonant bass sounds. What would you do? Well, if you’re Bart and Lisa in “Whacking Day,” you use the sultry vocal stylings of Barry White. In addition to providing some sweet vocals, he gets a couple of good comedy bits in the episode, as well.

10. U2

The best joke involving U2 in “Trash of the Titans,” the 200th episode of The Simpsons, involves Homer disguising himself as their “potato man” to get backstage. However, the band also gets a few jokes in, and actually appear a couple of times throughout the course of the episode. It’s not the meatiest appearance, but it’s one of the funnier ones.

9. Linda Ronstadt

Linda Ronstadt may not have the name recognition of others on this list, at least in the modern era, but her appearance in Barney’s Plow King commercial is fantastic, nevertheless.

8. James Brown

The greatness of James Brown’s appearance in “Bart’s Inner Child” hinges entirely on his delivery of one single line: “Wait a minute, this bandstand wasn’t double bolted!” Nothing more needs to be said.

7. Joey Kramer

Kramer first appeared alongside the other members of Aerosmith. Then, he got to come back by himself. Yes, Joey Kramer. Not Steven Tyler. Not Joe Perry. Joey Kramer. Why? Because, in his first appearance, he’s seduced by Mrs. Krabappel. As such, when Ned and Edna start dating, and the other men in the bar are remembering their time with Edna, Kramer is included. It was unexpected, but a delightful, and very funny callback.

6. Mick Jagger & Keith Richards

They were billed separately, but the two lead figures of The Rolling Stones are joined together for this list. Once again, we go back to “How I Spent My Strummer Vacation,” in which Jagger and Richards got the bulk of the lines among the musical guest stars. Have you ever wanted to hear Richards say he has to put up the storm windows because winter is coming? Of course you have, and you can only do it here.

5. Paul McCartney

You could list this as Paul and Linda McCartney, as they both appeared, unsurprisingly, in “Lisa the Vegetarian.” Paul, steadfast vegetarian that he is, provides advice and encouragement for Lisa as she learns to deal with her meat-loving father. Then, Apu sings “Sgt. Pepper’s Lonely Hearts Club Band” as Paul and Linda bop to the beat. Maybe not the funniest appearance, but still humorous, and also pretty strong from a dramatic perspective.

4. The White Stripes

The White Stripes play a song, and they also get into a fight with Bart and chase him through town until they fall into a river. It’s this high on the list for the moment when Meg shouts “Let’s kick his ass!” You never get to see Meg these days. Even when you did, you could never imagine her shouting anything. That’s what makes this so delightful.

3. Weird Al Yankovic

Weird Al has shown up twice on the show, including in the divisive retconning episode “That ’90s Show.” He sings parody songs both times because the show knows to play to Weird Al’s strengths. Basically, if you love Weird Al, his appearances are great, and what person in their right mind doesn’t love Weird Al?

2. The Ramones

Just as with their music, The Ramones’ time in “Rosebud” is short, to the point, and tremendous. They show up, talk jive about Mr. Burns, sing him a birthday song, and that’s that. Maybe Smithers was wrong when he called them four young men who were sure to go far. Either way, it’s fantastic.

1. Peter Frampton

On the audio commentary for “Homerpalooza,” showrunners Bill Oakley and Josh Weinstein speak effusively about Frampton, and somebody even mentions at some point that they wanted to do further TV work with him. It makes sense, as Frampton, for a guy who’s done very little acting, really nails his voice work. He gets to play an angry older gentleman fed up with the younger, hipper acts he’s stuck on tour with. After all, if Sonic Youth was raiding your cooler, you’d be annoyed, too.