With over 700 episodes, The Simpsons has played host to more than 900 guest stars, and over 1,500 guest appearances. Whether it’s Mark Hamill trying to save convention goers on long distance, Homer sharing his “Lawn Mower” recipe —vodka and wheat grass juice, if you’re wondering— with Ron Howard, or Leonard Nimoy sending off the Monorail on its maiden voyage, celebrities have always been part of the lifeblood of Springfield.
But what the above guest stars have in common is that they each portrayed themselves, which has been the path for the majority of celebrity appearances on The Simpsons. The remainder, however, is made up of celebrities who were given their own unique character, allowing them to integrate into storylines in a much different way than their self-portraying counterparts. The result has been some of the most enduring characters in the Simpson universe. So, naturally, let’s try to rank the best ones.
11. Patrick Stewart - Number One (“Homer the Great,” Season 6)
Appearing as the local chapter leader of the Masonic Stonecutters cult, Stewart presides over one of the most beloved Simpsons musical numbers, and lends his gravitas to a character that doesn’t need to do too much other than be commanding. Which is exactly how he sounds when we hear lines like, "Let's all get drunk and play ping-pong!" Naming his character “Number One” is homage to Stewart’s role as Captain Jean-Luc Picard in Star Trek: The Next Generation, where he often referred to his second-in-command by the same name.
10. David Duchovny and Gillian Anderson - Fox Mulder and Dana Scully (“The Springfield Files,” Season 8)
Part of an excellent run of episodes in Season 8, and overflowing with references to The X-Files, In Search Of…,and Close Encounters of the Third Kind, “The Springfield Files” contains a rare sort of guest appearance where a guest star takes on the role of a character they portray in another franchise. Here, we get FBI agents Mulder and Scully probing Homer after his “alien” encounter, complete with Mulder’s hyperbolic insistence concerning the existence of extraterrestrial life.
9. Jane Kaczmarek - Judge Constance Harm (“The Parent Rap,” Season 13)
Season 13 always felt like a turning point for The Simpsons. As the first season that featured Al Jean as showrunner, there is a tangible difference in the scattered nature of the narratives (“Brawl in the Family,” “Blame it on Lisa,” etc.) versus previous seasons, a big deal for a show that relied on precision of satirical wit when at its best. But in this season —a year that saw Malcolm in the Middle and The Simpsons as Fox’s two highest-rated shows— Jane Kaczmarek arrives as the hotheaded Judge Constance Harm, who is, more or less, a judicial equivalent to her character, Lois Wilkerson, on Malcolm. She has appeared several times as Judge Harm, but in this episode we are gifted with one of the better exchanges between Homer and a guest star:
Homer: Uh, your Honor, I was chasing the KBBL Party Penguin Prize Patrol.
Judge Harm: You abandoned your son to win forty dollars?
Homer: And a Blue Oyster Cult medallion.
Judge Harm: And that was more important than keeping your son out of trouble?
Homer: Your Honor, if I may sing a little bit of, "Don't Fear the Reaper," I think you'll agree...
Judge Harm: I'm familiar with BOC. But you have got a boy here who is crying out for adult supervision.
Homer : I couldn't agree more! Perhaps some sort of court-appointed babysitter or au pair.
8. Jon Lovitz - Llewellyn Sinclair (“A Streetcar Named Marge,” Season 4)
Jon Lovitz has appeared several times across the series as a variety of characters (Jay Sherman the movie critic, Marge’s old boyfriend Artie Ziff, etc.), but his one-off appearance as the local theater director of Oh, Streetcar! — a musical rendition of Tennessee Williams’ play, A Streetcar Named Desire— may be his best: "I have directed three plays in my career, and I have had three heart attacks!" Not only did this episode become a Simpsons classic, it also started a fight with the city of New Orleans.
7. Kathleen Turner - Stacy Lovell (“Lisa vs. Malibu Stacy,” Season 5)
The Simpsons take on Barbie, references to Lisa’s (and Mr. Smithers’) interest in Malibu Stacy appear several times throughout the show, but in this Season 5 gem, Kathleen Turner shows up to voice the woman who started the whole enterprise before she was forced out in 1974: “They said my way of thinking just wasn’t cost effective...well, that and I was funnelling profits to the Viet Cong." The seven-time-married, alcoholic Stacy arrives to help Lisa combat the blatant sexism surrounding the doll (“Don’t blame me, I’m just a girl!”), and we are treated to one of the best episodes in a season full of all-timers.
6. David Hyde Pierce - Cecil Terwilliger (“Brother From Another Series,” Season 8)
Given Kelsey Grammer's long-tenured involvement with The Simpsons (more on him in a bit), it was perhaps only a matter of time before Grammer's long-time fraternal co-star on Frasier would make an appearance in Springfield. In "Brother from Another Series" (and a few additional episodes later on), we get Pierce playing Niles Cra...I mean, Cecil Terwilliger —the jealous, soft-spoken younger brother of Grammer's Sideshow Bob. The result is basically a 22-minute-long Frasier reference, and it rules.
5. Johnny Cash - Coyote Spirit Guide (“The Mysterious Voyage of Our Homer,” Season 8)
When Homer goes off into a mystical dream world after eating a Guatemalan insanity pepper, he is met by his coyote spirit guide, played by the Man in Black himself. This episode aired in 1997, which was between the second and third releases of Cash’s career-resurgent American recordings. These recordings cemented Cash as the mystical, shaman-like figure that he became in his final decade, making him not only the perfect voice for a character like this, but also the perfect conceptual figure, like if the showrunners decided to cast Leonard Cohen. Take that, space coyote!
4. Joe Mantegna - Fat Tony (Recurring)
“I don’t get mad; I get stabby.” Mantegna’s Fat Tony, Springfield’s local mafia boss, has appeared since the third season of the show, when he and the rest of the Springfield crime syndicate were busy employing, defending, and ultimately betraying Bart (“Bart the Murderer”). Though Fat Tony dies of a heartattack in Season 22’s “Donnie Fatso,” he is replaced by a thinner cousin, who promptly gains weight and becomes an identical character by the episode’s end (*insert eye-roll here*). Lame plotlines notwithstanding, it is hard to argue many guests who have been more integral to the world of Springfield for such a long period of time, and every appearance of Fat Tony in the first decade-plus of the series is an offer you can’t refuse.
3. Albert Brooks - Hank Scorpio (“You Only Move Twice,” Season 8); Brad Goodman (“Bart’s Inner Child,” Season 5)
A theme of this list is that Season 8 was a goldmine for guest stars not portraying themselves. Though Albert Brooks has appeared in eight Simpsons episodes to date (plus The Simpsons Movie), it is his appearance as would-be James Bond villain/Homer’s boss at Globex Corporation, Hank Scorpio, that is most enduring. He conquers the East Coast and buys Homer the Denver Broncos in appreciation of his work, getting Homer closer to his dream of owning the Dallas Cowboys (“You just don’t understand football, Marge”).
However, not mentioning Brooks' appearance in Season 5 as self-help therapist, Brad Goodman, would be a travesty. He claims his credentials are valid because he has “a PhD in pain,” and that he can help you with any personality disorder in the “Feel Bad Rainbow” —I bet you didn’t know that “Uncontrollable Falling Down” was a personality disorder. Thanks to Brad Goodman, and Albert Brooks, now you know.
2. Kelsey Grammer - Sideshow Bob Terwilliger (Recurring)
Sideshow Bob has been around since the first season of The Simpsons, where he framed Krusty the Clown for murder, was subsequently foiled by Bart’s unwavering belief in Krusty’s innocence (“Krusty Gets Busted”), and began one of the show’s longest storylines —Sideshow Bob’s desire to brutally murder Bart Simpson. More so than any other guest character, Sideshow Bob is part of the wider cultural landscape, recognizable to people even outside of the fanbase.
Maybe we love Sideshow Bob because of Grammer’s vocal gravitas, or maybe it’s Bob’s love of singing showtunes (H.M.S. Pinafore, anyone?). Both are possible, but it’s more probable that we love him because of this line: “I am presently incarcerated, imprisoned for a crime I didn’t even commit! ‘Attempted murder?’ Now honestly, what is that? Do they give a Nobel prize for ‘attempted chemistry?’”
1. Phil Hartman - Troy McClure / Lionel Hutz (Recurring, Seasons 2-10)
Sideshow Bob may be the cultural touchstone of guest characters on The Simpsons, but it is genuinely difficult to imagine the best years of the show without Phil Hartman’s talents. While he played many one-off characters —some memorable, like Monorail con artist, Lyle Lanley, and his Monorail Song — it was his regular appearances as washed-up actor, Troy McClure, and bargain-bin lawyer, Lionel Hutz, that made Hartman an indispensable part of The Simpsons' first decade.
It is difficult to properly value Hartman’s characters in such a small space, as they were constantly providing top-tier contributions in the years prior to his tragic death in 1998. Whether it’s Troy McClure’s big Hollywood comeback attempt (“A Fish Called Selma”), Lionel Hutz defending Marge in court (“Marge in Chains”) or teaching her the ropes of being a realtor (“Realty Bites”), or one of dozens of throwaway moments that are as funny as anything in the series, it’s not an overstatement to wonder how different this show may have looked were it not for Hartman, and what it may have looked like if he were still here.