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The Greatest Guest Appearances in The Simpsons History  

Derrick Deane
8.1k votes 633 voters 26.1k views 75 items

With 25+ seasons completed and seemingly no end in sight, there is certainly no shortage on the number of celebrity guest stars who have visited Springfield, leaving their mark on The Simpsons. These Simpsons cameos, guest-starring roles, and guest voices are just one part of what makes The Simpsons so fun to watch, and easily one of the best TV shows of all time.

The longest running scripted prime-time television series has welcomed comedy legends like Bob Hope, Mel Brooks, and Johnny Carson onto the show as well as veteran actors like Donald Sutherland, Leonard Nimoy, and Patrick Stewart among many others. Modern superstars like Anne Hathaway, Daniel Radcliffe, and Neil Patrick Harris have guest starred along with legends like George Carlin, Stan Lee, and Johnny Cash.

And then of course there are Troy McClure and Lionel Hutz, voiced by the late Phil Hartman and the fan favorite mob boss Fat Tony voiced by Joe Mantegna. David Duchovny, Betty White, John Goodman, Lucy Lawless, Danny DeVito, Alec Baldwin, Mark Hamill, Rodney Dangerfield, Michael Jackson - the list of guest stars and Simpsons celebrity guests is as wide and diverse as the cast of characters that populate Springfield. 

We've gathered the top, greatest guest stars in The Simpsons history (though bands like Aerosmith, The Ramones, Smashing Pumpkins, etc. have been omitted) and we know there are more than a few favorites on this list of Simpsons guest stars. Which guest voices on The Simpsons are your favorites?
Michael Jackson is listed (or ranked) 1 on the list The Greatest Guest Appearances in The Simpsons History
Photo:  Wikimedia Commons (CC-BY)
"Lisa, it's your birthday. Happy birthday, Lisa." While Kipp Lennon did all the singing in this season three premiere episode, Michael Jackson provided the dialogue and was credited as John Jay Smith for his appearance. Leon Kompowsky would appear again in the season 13 episode "Sweets and Sour Marge" and in a season 23 couch gag.
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Phil Hartman is listed (or ranked) 2 on the list The Greatest Guest Appearances in The Simpsons History
Photo:  Wikimedia Commons (CC-BY)

Regardless of whether you think Phil Hartman was a guest star or portrayed a supporting character, his Troy McClure and Lionel Hutz are but a handful of side characters who were a part of the early, formative years of The Simpsons.

His first appearance came in season two as Lionel Hutz in the episode "Bart Gets Hit by a Car." Three episodes later, he would debut Troy McClure in "Homer vs. Lisa and the 8th Commandment(he also voiced the cable guy and Moses in that episode). Other characters Hartman voiced before his death were Lyle Lanley, Mr. Muntz, Mandy Patinkin, and Bill Clinton, among many others.
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Patrick Stewart is listed (or ranked) 3 on the list The Greatest Guest Appearances in The Simpsons History
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Leader of the Springfield chapter of the secret Stonecutter society, Patrick Stewart guest starred as Number One in the season six episode "Homer the Great." He gleefully hazes new recruits and enjoys presiding over the club's many social gatherings... and who can forget the awesome Stonecutters song?
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Kelsey Grammer is listed (or ranked) 4 on the list The Greatest Guest Appearances in The Simpsons History
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Whenever Kelsey Grammer guest starred on The Simpsons, it felt like a special event. He has appeared as Bart's nemesis, Sideshow Bob, 12 times, beginning with his botched season one attempt at framing Krusty the Clown. Bob would appear again in seasons three, five through eight, 12, 14, 17, and 19 through 21. Grammer also recorded the part of Sideshow Bob for The Simpsons Movie, but it was eventually cut.
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