The Simpsons are a cultural icon that first jumped onto television screens way back in 1987. Now into its 23rd season and approaching their 500th episode the show is the longest-running American sitcom, the longest-running American animated program, and the longest-running American primetime, scripted television series.

But it isn’t just the core group of characters that The Simpsons is famous for. It also pioneered the idea of celebrity cameos paving the way for other animated series. To celebrate the approaching milestone of 500 episodes we thought we’d dive into the archives and bring you our favourite musician cameos from over 24 years of laughs. Enjoy.

The Simpsons are a cultural icon that first jumped onto television screens way back in 1987. Now into its 23rd season and approaching their 500th episode the show is the longest-running American sitcom, the longest-running American animated program, and the longest-running American primetime, scripted television series. But it isn't just the core group of characters that The Simpsons is famous for. It also pioneered the idea of celebrity cameos paving the way for other animated series. To celebrate the approaching milestone of 500 episodes we thought we'd dive into the archives and bring you our favourite musician cameos from over 24 years of laughs. Enjoy.
Mick Jagger, Keith Richards, Lenny Kravitz, Elvis Costello, Tom Petty, Brian Setzer - Season 14
Cypress Hill - Season 7
Blink 182 - Season 14
Barry White - Season 4
Johnny Cash - Season 8
Aerosmith - Season 3
Coldplay - Season 21
50 Cent - Season 16
James Brown - Season 5
Metallica - Season 18
Red Hot Chili Peppers - Season 4
The Ramones - Season 5
Green Day -The Simpsons Movie
The Smashing Pumpkins - Season 7
Tom Jones - Season 4
REM - Season 13
The White Stripes - Season 18
Weird Al Yankovic - Season 14
U2 - Season 9th
George Harrison - Season 5
Paul McCartney - Season 7
Ringo Starr - Season 2
Sting - Season 3
Tony Bennett - Season 2
Peter Frampton - Season 7
Lionel Ritchie - Season 19
Willie Nelson - Season 11 "Behind the Laughter" is the twenty-second episode of The Simpsons eleventh season. It first aired in the United States on the Fox network on May 21, 2000. In the episode, which is a parody of the VH1 series Behind the Music, the Simpson family are portrayed as actors on a sitcom, and their dramatic inner turmoil and struggles are detailed. Told in a narrative format, the episode tells a fictional story of how The Simpsons began. The plot idea for the episode was pitched by Long, and the writers wrote the episode quickly without a draft. VH1 and the producers of Behind the Music allowed the crew to use the show's visual graphics package, and Jim Forbes, narrator for the show, also came in to record narrations for the episode. In addition, country musician Willie Nelson guest stars as himself.
The Who - Season 12 "A Tale of Two Springfields" is the second episode from season twelve of the animated TV series The Simpsons and is the 250th episode of the series overall in both broadcast and production order. The episode originally premiered November 5, 2000 on Fox Broadcasting Company. The episode was written by John Swartzwelder and directed by Shaun Cashman and guest starred The Who. The episode was inspired by Don Payne based on Don's mom's area where one side would spread rumors of the other side. Larry Doyle then pitched it to have the both sides divide, because of area code. The episode features cultural references to The Who and Freedom of Speech and has also received positive reviews from critics.
Sonic Youth - Season 7 "Homerpalooza" is the 24th episode of The Simpsons' seventh season and originally aired on May 19, 1996. The plot focuses around Homer's depression about aging and no longer being cool, and his quest to become cool again by joining the "Hullabalooza" music festival as a carnival freak. The episode title is a play on the Lollapalooza music festival. It would prove to be the last Simpsons episode written by Brent Forrester and the last episode directed by Wes Archer. Peter Frampton and musical groups The Smashing Pumpkins, Cypress Hill and Sonic Youth guest star as themselves.
Phish - Season 13 In "Weekend at Burnsies" on The Simpsons, Phish guest stars when Homer Simpson is prescribed medical marijuana and becomes addicted. Mr. Burns hopes to use Homer at his shareholder's meeting, making Homer laugh at everything he says, but a new law is passed that prohibits medical marijuana. So Burns fakes his death, but Smithers and Homer animate his body (a la Weekend at Bernie's) and convince the shareholders to continue funding the power plant.
David Crosby - Season 5 "Homer's Barbershop Quartet" is the first episode of The Simpsons' fifth season. The episode was written by Jeff Martin and directed by Mark Kirkland. It features The Be Sharps, a barbershop quartet founded by Homer Simpson. The band's story roughly parallels that of The Beatles. George Harrison and David Crosby guest star as themselves, and The Dapper Dans provide the singing voices of The Be Sharps.
Elton John - Season 10 & 18

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