Random Greatest Guest Appearances in The Simpsons History (75 items)

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  (#1) Kelsey Grammer

  • 1955-02-21

  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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  (#2) Phil Hartman

  • 1948-09-24

  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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  (#3) Leonard Nimoy

  • 1931-03-26

  Before Lenoard Nimoy guest starred in "The Springfield Files" with The X-Files stars David Duchovny and Gillian Anderson in season eight, he appeared as himself in the classic season four episode "Marge vs. the Monorail." After appearing at the launch of the the monorail's maiden voyage, Nimoy appears again after catastrophe has miraculously been averted. After he says his work is done, Barney says he didn't do anything, to which Nimoy replies, "Didn't I?" and vanishes in the transporter effect similar to Star Trek.
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  (#4) Patrick Stewart

  • 1940-07-13

  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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  (#5) Anne Hathaway

  • 1982-11-12

  Say what you will about Anne Hathaway, but she has two guest appearances on The Simpsons to go along with all her other career accomplishments. Her first appearance came in season 20 as Jenny, a young girl with whom Bart briefly falls in love. Hathaway returned the following season as Princess Penelope in the season 21 episode "Once Upon a Time in Springfield" with guest stars Eartha Kitt, Jackie Mason and Gary Larson. In hopes of attracting more female viewers, Princess Penelope was added to The Krusty the Clown Show and she almost ends up married to Krusty.
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  (#6) David Duchovny

  • 1960-08-07

  Caipitalizing on the popularity of another Fox show, The X-Files stars David Duchovny and Gillian Anderson guest starred as Simpson-ized versions of Mulder and Scully. The episode titled "The Springfield Files," in which Leonard Nimoy also guest starred, centered on Homer witnessing something out in the woods near Springfield, but no one believed him.
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  (#7) Danny DeVito

  • 1944-11-17

  In season two, Danny DeVito lent his voice to Herbert "Herb" Powell, Homer's older half-brother. The character returned in season three as Herb went on to rebuild his fortune after inventing a device that translated infantile speech into English. Herb is the result of a short-lived affair between Abraham Simpson and an unnamed female carnival worker.
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  (#8) Michael Jackson

  • 1958-08-29

  "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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  (#9) Johnny Cash

  • 1932-02-26

  The Man in Black aka Johnny Cash guest starred as the Coyote in Homer's desert hallucination in season eight. The Coyote told Homer to "find your soul mate." The Coyote also appeared in a non-speaking cameo in "Blazed and Confused" when Marge is hallucinating.
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  (#10) Joe Mantegna

  • 1947-11-13

  Ever wondered who voiced Fat Tony? It was none other than Joe Mantegna who has portrayed the mobster boss in 21 episodes. He currently holds the record for most guest performances by a living actor (Phil Hartman and Marcia Wallace rank higher than him overall). Fat Tony first appeared in season three in an episode that also featured Neil Patrick Harris.
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  (#11) Stephen Hawking

  • 1942-01-08

  Stephen Hawking guest starred as himself in the next to last episode of season 10. In the episode "They Saved Lisa's Brain," Hawking makes a surprise appearance at a MENSA meeting in the park to critique the group's crumbling utopia. He later talked about his guest starring role on the show.
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  (#12) James Earl Jones

  • 1931-01-17

  James Earl Jones has guest starred on The Simpsons several times voicing various characters and even appeared as Maggie (yes, Maggie), in "Treehouse of Horror." When Homer visited an alternate universe, Maggie hit Groundskeeper Willie in the back with an axe and then spoke in Jones' voice saying, "This is indeed a disturbing universe." He appeared again as Serak the Preparer, a Rigellian cohort of Kang and Kodos and a third time as a moving man in the "Treehouse of Horror" tale "Bad Dream House."
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  (#13) Mark Hamill

  • 1951-09-25

  To say Star Wars has been very good to Mark Hamill would be a severe understatement. He appeared as himself in the season 10 episode "Mayored to the Mob" in which he hires Homer to become his personal bodyguard after a crowd mobs him at the Springfield Bi-Mon-Sci-Fi-Con. Among the highlights from the episode are Homer carrying Hamill Bodyguard-style through a crowd of people, Hamill performing "Luke, Be A Jedi Tonight," and Hamill telling Homer to "Use the forks!"
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  (#14) Ringo Starr

  • 1940-07-07

  Ringo Starr guest starred as himself in the season two episode Brush with Greatness in which Marge's interest in art is renewed when Homer finds old portraits of her high school crush Ringo Starr. She takes an art class at a local college (Professor Lombardo was voiced by Jon Lovitz), wins an art competition, and is commissioned to paint a portrait of Mr. Burns. Meanwhile, Marge reveals that she sent a painting to Starr for "an honest opinion" but never heard back. While conceding that she can't paint a "beautiful" portrait of Mr. Burns, she gets some much needed encouragement in the form of a reply from Starr, who apologizes for the long delay.
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  (#15) Dustin Hoffman

  • 1937-08-08

  Mr. Bergstrom! Dustin Hoffman played the charismatic, self-effacing, and encouraging substitute teacher who filled in for Ms. Hoover. Lisa immediately took to him because he was the kind of male role model she was seeking in her life. The tearful ending is one of the most heartbreaking in Simpsons history.
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  (#16) Albert Brooks

  • 1947-07-22

  Albert Brooks has been a frequent guest voice on The Simpsons and is always credited as "A. Brooks." He appeared twice in the first season, first as Cowboy Bob and two episodes later as Jacques, the French bowler who sweeps Marge off her feet. He returned in season five to voice Brad Goodman and McGarnagle and then again in season eight as Hank Scorpio. He returned again in season 16 as Tab Spangler and also voiced the antagonist Russ Cargill in The Simpsons Movie.
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  (#17) Paul McCartney

  • 1942-06-18

  Paul McCartney and his then-wife Linda guest starred in the season seven episode "Lisa the Vegetarian" in which Lisa finds herself unable to eat lamb after visiting the boring amusement park, Storytown Village. She is exposed to ridicule and resentment from Homer and friends but with the help of Apu and the McCartneys, makes an effort to stick to her new vegetarian ways.
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  (#18) Michelle Pfeiffer

  • 1958-04-29

  Michelle Pfeiffer voiced Springfield Nuclear Power Plant employee Mindy Simmons who, much to Homer's misfortune, likes all the same things he does. When he meets her at work, he finds himself extremely attracted to her and a threat to his marriage. In the end, regardless of how tempting she may be, Homer decides to stay faithful to Marge.
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  (#19) David Hyde Pierce

  • 1959-04-03

  Just like every hero needs a sidekick, so does a villain. David Hyde Pierce teamed up with his Fraiser co-star Kelsey Grammer to play Cecil Terwillinger in the season eight episode "Brother from Another Series." They teamed up again in season 19's "Funeral for a Fiend" which guest starred another Fraiser alum, John Mahoney.
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  (#20) Stan Lee

  • 1922-12-28

  The Generalissimo appears in season 13 as himself as he pays a visit to Comic Book Guy's store to make the Batmobile "better" and (not) Hulk out on the street. Lee returned with author Harlan Ellison to guest star in season 23.
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  (#21) Barry White

  • 1944-09-12

  He does love the slither of a sexy lady snake. Baritone R&B crooner Barry White guest starred as himself twice in Season 4. First, he appeared in an attempt to save the snakes from the annual tradition of Whacking Day. Two episodes later, White appeared again as part of the all-star line up of celebrities at the Krusty the Clown special in Krusty Gets Kancelled.
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  (#22) Rodney Dangerfield

  • 1921-11-22

  Comedy legend Rodney Dangerfield guest starred as Mr. Burns' son Larry. After growing up in an orphanage, he tracked down his father while working at a souvenir stand. He ends up getting a job at the nuclear power plant, but his lack of intelligence, lack of manners, and fondness of drinking angers Mr. Burns who ends up disowning him. Rodney Dangerfield also appeared in another episode, but was voiced by Hank Azaria.
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  (#23) Meryl Streep

  • 1949-06-22

  Who else are you going to get voice Bart's first girlfriend besides Meryl Streep? Streep voices Reverend Lovejoy's daughter Jessica Lovejoy in the season six episode, "Bart's Girlfriend." While appearing sweet and innocent on the outside, Jessica is actually a mischievous femme fatale hell-raiser. She uses her beauty to manipulate boys and tells Bart, "You're bad, and I like it."
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  (#24) Glenn Close

  • 1947-03-19

  Glenn Close guest stars as Homer's mother, Mona Simpson in seasons 7, 15 and 19. In total, she guest starred in four episodes before her character died in the season 19 episode "Mona Leaves-a" (which also featured a guest performance by Lance Armstrong). However, she continues to live on in Homer's dreams.
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  (#25) James Woods

  • 1947-04-18

  Visiting Springfield in season five to research for an upcoming role, James Woods stars as himself in the episode "Homer and Apu." The episode centers on Apu losing his job at the Kwik-E-Mart after selling tainted meat to Homer. Feeling bad, Homer lets Apu live at the Simpson's home while he is unemployed. Meanwhile, Woods fills in Apu's position at the convenience store. 
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  (#26) George Harrison

  • 1943-02-25

  Season five kicked off with "Homer's Barbershop Quartet." The Beatles guitarist George Harrison guest starred as himself as did fellow musician David Crosby. Harrison's line at the end of the episode ("It's been done.") was a reference to the famous impromptu concert The Beatles had on top of the Apple Records building in 1969.
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  (#27) Buzz Aldrin

  • 1930-01-20

  If you're going to take a trip into deep space, Buzz Aldrin is just the guy you want as you co-pilot. The famous astronaut guest starred in the season five episode which saw NASA launch Homer into space in an attempt to reverse declining TV ratings.
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  (#28) George Carlin

  • 1937-05-12

  Legendary comedian George Carlin voiced the role of Munchie, the co-owner of Groovy Grove Juice. A friend of Homer's mom, Mona Simpson from the '60s, Seth and his friend/co-owner Seth (voiced by Martin Mull), the two are swept up in a plot by Homer to "shake up the squares." Seth and Munchie appear in a few other episodes ("Weekend at Burnsie's" and "Mona Leaves-a") as well as The Simpsons Movie.
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  (#29) Kirk Douglas

  • 1916-12-09

  Legendary actor Kirk Douglas appeared in the season seven episode "The Day the Violence Died," voicing Chester Lampwick, the original creator of The Itchy & Scratchy Show. Lampwick became a bum after he said Roger Meyer Sr. stole his idea and refused to pay him. With Bart's help, he sues Itchy and Scratchy Studios for $800 million and wins. Lampwick is seen in The Simpsons Movie in tatters, suggesting he went back to being a bum.
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  (#30) Betty White

  • 1922-01-17

  Betty White guest stars as a PBS pledge drive host in the season 11 episode "Missionary: Impossible." Tired of interruptions during the British sitcom Do Shut Up, Homer pledges $10,000 to the network. Clearly not having the money, White and a mob of PBS characters including Mr. Rogers and the Teletubbies chase him through the streets. After fleeing to the church and seeking help from Reverend Lovejoy, Homer is shipped off on a cargo plane to the South Pacific to become a missionary.
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  (#31) John Goodman

  • 1952-06-20

  John Goodman voiced the biker gang leader Meathook in the season 11 episode "Take My Wife, Sleaze." Henry Winkler voiced his biker gang buddy, Ramrod.
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  (#32) Mel Brooks

  • 1926-06-28

  Season six of The Simpsons saw a significant number of celebrity guest stars and one of them was comedy legend Mel Brooks. In the episode where Bart become a ballet star at school, Homer lost all of his money in pumpkin stocks and must turn to Patty and Selma for a loan. The sisters seize the opportunity to make Homer their loyal servant and turn his life into a living hell. The episode ends with Homer as a limo driver who chauffeurs Brooks.
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  (#33) Johnny Carson

  • 1925-10-23

  In the Krusty Gets Kancelled comedy legend and former Tonight Show host Johnny Carson guest starred. With Carson's guest role, the only Tonight Show hosts to not appear on The Simpsons are Jimmy Fallon, '60s host Jack Paar, and Al Collins and Jack Lescoulie (they co-hosted for six months in 1957).
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  (#34) Lucy Lawless

  • 1968-03-29

  Lucy Lawless appeared as herself dressed as Xena: Warrior Princess in "Treehouse of Horror X." The segment titled "Desperately Xeeking Xena" saw Bart and Lisa become superheroes (Stretch Dude and Clobber Girl) and take on Comic Book Guy who portrays a villain called The Collector. The annual Halloween special also featured cameos by Tom Arnold, Dick Clark, and Frank Welker all playing themselves.
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  (#35) Donald Sutherland

  • 1935-07-17

  Donald Sutherland voiced the comically named head of the Springfield Historical Society, Hollis Hurlbut. In the season seven episode "Lisa the Iconoclast," a secret confession is revealed that Jebediah Springfield was a fraud. The town decides to dig up the skeleton of Springfield to prove that he didn't have a silver tongue. Hurlbut pries the coffin open and pockets the tongue before the dust can settle.
  
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  (#36) John Waters

  • 1946-04-22

  "Zzzzz-ap!" Cult film director John Waters guest starred as John, the gay owner of Cockamamie's Collectibles Shop in the season eight episode, "Homer's Phobia." It is hinted that John and Waylon Smithers have been dating and Homer fears that John's homosexuality is rubbing off on Bart. John is also seen in the crowd in a couple of other The Simpsons episodes - "The Fool Monty" (in the background with blonde hair) and "Flaming Moe" (in the crowd during Moe's speech).
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  (#37) Robert Englund

  • 1947-06-06

  Robert Englund brought his iconic horror character Freddy Kreuger to "Treehouse of Horror IX" in the opening couch gag. Freddy and Jason are sitting on the couch when Freddy asks where the Simpsons are, to which Jason says, "Eh. Whaddya going to do?" (despite the fact that he normally never speaks). The character has also appeared in other seasons of the show including "Treehouse of Horror V" as he and other movie and TV monsters attacked Homer. The following year, Groundskeeper Willie is burned to death but returns as a Simpson-ized version of Freddy in "Treehouse of Horror VI."
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  (#38) Elizabeth Taylor

  • 1932-02-27

  The voice behind Maggie's first word ("Daddy"), Elizabeth Taylor guest starred twice on The Simpsons. In addition to the one word cameo in "Lisa's First Word," she also starred as herself in the guest star heavy episode "Krusty Gets Kancelled."
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  (#39) Mickey Rooney

  • 1920-09-23

  "Jiminy Jillikers! Jiminy Jillikers!" The Mickster guest starred to help Milhouse deal with being an adored child actor following his landing the sidekick role in the Radioactive Man movie. Season 26 is slated to have an episode dedicated to his memory. Mickey Rooney passed away on April 6, 2014 at the age of 93.
  
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  (#40) Jon Lovitz

  • 1957-07-21

  Jon Lovitz has voiced many characters on The Simpsons, most frequently and memorably, Marge's grade school boyfriend Artie Ziff. In addition to Ziff, Lovitz has also voiced Mr. Seckofsky, Professor Lombardo, Aristotle Amadopolis, Llewellyn Sinclair, Enrico Irritazio, and The Critic's Jay Sherman.
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  (#41) Conan O'Brien

  • 1963-04-18

  The talk show host and former Simpsons writer guest starred as himself in the season five episode "Bart Gets Famous." As Bart gains instant popularity with the catch phrase, "I didn't do it," he eventually winds up on Conan's late night talk show. But remember, only Conan may dance.
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  (#42) Mel Gibson

  • 1956-01-03

  Mel Gibson joined the list of guest stars with a memorable appearance in the season 11 premiere "Beyond Blunderdome." In the episode, Homer and Marge go to a preview screening of Gibson's new movie and everyone loves it except for Homer. After reading his response card which states, "Oh, Mel, it's the most boring piece of garbage I've ever seen, and it's not easy for me to say that," he asks Homer to help him make the movie good. Together, they turn the movie into an extremely violent action film that the studio doesn't like.
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  (#43) Bob Hope

  • 1903-05-29

  Bob Hope has the rare distinction of guest starring on the show and also being portrayed by another voice actor. While Canadian comedian Dave Thomas portrayed him in a season 17 episode (long after Mr. Hope had passed), the comedy legend appeared as himself in the season four episode "Lisa the Beauty Queen."
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  (#44) Alec Baldwin

  • 1958-04-03

  Alec Baldwin first appeared in a season 10 episode alongside his then-wife Kim Basinger, director Ron Howard and producer Brian Grazer. He returned in season 17 to voice Caleb Thorn.
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  (#45) Cloris Leachman

  • 1926-04-30

  Cloris Leachman guest starred as Mrs. Glick, the old lady for whom Bart does chores in order to save up money to buy the Radioactive Man #1 comic book. With a penchant for using iodine on Bart's cuts and scratches from yard work, she pays him very poorly for his efforts. It is believed that Mrs. Glick was suffering from dementia.
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  (#46) Lisa Kudrow

  • 1963-07-30

  Season 10 kicked off with Lisa Kudrow guest starring as Alex Whitney, the popular "grown-up" girl in Lisa's class. Lisa becomes jealous of her because Alex steals her friends. Alex is seen in a couple of other episodes when she lines up for a gymnastics class with Lisa and also joins a tap dancing school owned by Vicki Valentine.
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  (#47) Willem Dafoe

  • 1955-07-22

  Willem Dafoe voiced The Commandant in the season eight episode "The Secret War of Lisa Simpson." As the head of Rommelwood Military School, The Commandant faces a unique request when Lisa requests to be sent to the school with Bart.
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  (#48) Martin Sheen

  • 1940-08-03

  Season nine provided a turning point for the character of Seymour Skinner. Martin Sheen guest starred to voice the real (Sargeant) Seymour Skinner and we all found out that the guy running Springfield Elementary was named Armin Tamzarian.
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  (#49) Jeff Goldblum

  • 1952-10-22

  Ever wondered who scored all those gigs that you may have seen Troy McClure in? MacArthur Parker is his name and Jeff Goldblum voiced the media agent in the season seven episode "A Fish Called Selma." The episode centered on Parker calling Troy to help him restart his career. Troy plays along by first courting then eventually marrying Selma. Parker tells Troy that he can get him the sidekick part in the new McBain movie McBain IV: Fatal Discharge, but says the newlyweds need to have a baby since the roles are going to "family men." They end up deciding against the idea and Selma leaves Troy, who rejects the McBain part.
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  (#50) Luke Perry

  • 1966-10-11

  Who could forget the classic sequence in which Luke Perry gets fired out of a cannon during Krusty's big comeback special? The season four episode saw the former 90210 star join other guest actors like Barry White, Johnny Carson, and the Red Hot Chili Peppers.

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