The Simpsons – 10 of the best Musical Guest Stars

Guest stars have enjoyed a turbulent relationship with The Simpsons. They didn’t become prominent parts of the series until well after Season Five (bar the odd cameo here or there), and, sadly, by the turn of the century, anyone from Lady Gaga to 50 Cent were popping up in Springfield for no discernible reason. Music acts were always featured from day one, however, and here I have tried to compile a list of some of the most entertaining stars to lend their voices.

10).      MIKE MILLS, R.E.M. – Homer the Moe

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This episode, in which Homer spitefully sets up his own ‘hunting club’ in his garage, is a prime example of The Simpsons’ ho-hum descent into easy jokes and jerkass Homer. Even though alternative rock gods R.E.M.’s appearance was a little shoehorned in, it was bespectacled bassist Mike Mills who got the best laugh; the fact he even attempted to use Homer’s makeshift urinal is humorous enough, let alone he is being rather perversely observed by Lenny.

Best line: “Guys, stand around me…I can’t go with Lenny watching.”

9).        ELVIS COSTELLO – How I Spent My Strummer Vacation

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In an episode littered with American icons of rock and roll (Mick and Keith, Tom Petty, Brian Setzer), it was Britain’s restless spirit Elvis Costello that had arguably the best performance in this pedestrian episode, coming across as a sycophantic kissass (“I’m telling Mr Jagger”) and desperately trying to push the bass guitar on anyone who’ll listen.

Best line: (after Homer rips off his fedora and glasses) “My image!”

8).        STING – Radio Bart

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To a 21st century audience, having Sting as a guest star might cause much confusion, but this was the early nineties, when he was more than just a strange choral artist. The episode is a classic, and Sting’s appearance invokes the schmaltzy, all-star charity single ‘We’re Sending Our Love…Down the Well.’ Krusty’s strained face is an image that’ll haunt me forever.

Best line: “Not while one of my fans needs me,” he says, before Marge tries to tell him Bart isn’t, and Homer pushes him out the way.

7).        SPINAL TAP – The Otto Show

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Despite not technically being a ‘real’ band, Spinal Tap were the perfect choice for an episode where Bart has a futile attempt at learning the guitar. The trio fit in some great one-liners, from being big in “Bulgaria and the other –garia”, to David St Hubbins’ complaint that “it’s supposed to be a rock concert, not the bleeding…splish splash show.” It even ends perfectly, too, with Spinal Tap’s tour bus exploding into a ball of flames. That’s another drummer gone.

Best line: “Goodnight, Springton, there will be no encores.”

6).        BILLY CORGAN, Smashing Pumpkins – Homerpalooza

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Homerpalooza splits some fans, with the anti-brigade lamenting its rampant appraisal of alternative rock, which looks kinda dated now. However, all the bands that participate are great, especially Smashing Pumpkins’ ringleader Billy Corgan, who even engages in some nice banter with Homer. It spawned the much-quoted line “Homer Simpson, smiling politely.” Props should also go to the following – Peter Frampton for playing a hackneyed curmudgeon, James Iha’s ironic quip (“people who made fun of you in school will now see what a successful freak you’ve become”) and Sonic Youth’s wooden delivery and excellent theme tune rendition.

Best line: (after Homer’s approval of their depressing music) “Well, we try to make a difference.”

 5).        BARRY WHITE – Whacking Day

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One of the many episodes that have become infamous, Whacking Day celebrates an annual tradition where adders are annihilated. Barry White is hired to unveil the ceremony, before unleashing his distaste at such a barbaric tradition. He later gets to augment his bull seal bellow, allowing his deep, walrus-esque bass tones to entice the snakes into the Simpsons home.

Best line: “I love to hear the sexy slither of a lady snake.”


4).        RINGO STARR – Brush With Greatness

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Another great episode, and it marks the first Beatle to appear. Marge’s adolescent admiration of the mop-topped Liverpudlian ends when Ringo never responds to her painting. He eventually replies, hanging the picture on his wall and fuelling Marge’s drive to paint Mr Burns. The fact he is replying to fan mail would later take a more humorous turn when he begged fans to stop sending him letters. With peace and love I’m warning you!

Best line: “Gear!”

3).        RED HOT CHILI PEPPERS – Krusty Gets Cancelled

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One of the first episodes to be awash with guest stars, Bart and Lisa recruited Hugh Hefner, Bette Midler and Luke Perry, among others, to get Krusty back on the gogglebox. Red Hot Chili Peppers were the musical act, who come up with a number of great lines – Krusty’s insistence on changing the lyrics to ‘Give It Away’ eventually gets Flea’s approval – “everyone can enjoy that!”

Best line: “Forget you, clown.”

2).        THE RAMONES – Rosebud

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Rosebud is twenty minutes of accurate homages, witty retorts and amusing one-liners. The Ramones’ snotty-nosed reluctance to play at Burns’ birthday party (“this gig sucks”, “yeah, up yours, Springfield”) is spot-on, as is their punk rendition of ‘Happy Birthday’. It also causes Burns to coldly, and inaccurately, say “have the Rolling Stones killed.”

Best line: Not really a line, but I love the disdain in which Joey says “happy birthday, BURNSIE!”

 1).        GEORGE HARRISON, The Beatles – Homer’s Barbershop Quartet

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One of the series’ landmark episodes, it perfectly parodied the Fab Four’s career trajectory, from Barney’s Japanese conceptual artist girlfriend, right through to Chief Wiggum becoming Springfield’s Pete Best. Not only is it one of the best episodes, it also has one of the greatest scenes, where Homer’s “best day of (his) life” isn’t actually meeting George Harrison – it’s finding a table full of brownies.

Best line: “(completely sincerely) What a nice fella!”

There were so many other great musicians to put in a good shift (James Taylor, Elton John, U2 and Tom Jones, to list just four), but for me, these 10 were perhaps understated, but did the job well.