Once upon a time, The Simpsons didn’t feature a guest star every other episode. Such appearances were rare—or at least semi-rare—enough to warrant the “special” in “special guest.” Moreover, the best of these appearances weren’t glorified cameos but original (or in one case, pseudo-original) characters in their own right, some of whom have gone on to become essential figures in Simpsons canon. We’ve compiled a list of the Simpsons’ most memorable and critically acclaimed guest characters in honour of the actors who adopted their animated roles as earnestly as they would for a movie part.
5 Michael Jackson – “Michael Jackson,” “Stark Raving Dad”
This first entry is a little more complex than the rest: in “Stark Raving Dad,” Michael Jackson voices a man who only thinks he is Michael Jackson (um, 13-year-old spoiler alert), which straddles the line between cameo and original character. In any case, “Michael Jackson,” born Leon Kompowsky, is a patient Homer meets when he is committed to a mental institution after he (against better judgment) lets Bart fill out his psychiatric profile. Kompowsky has spent years impersonating Jackson’s identity—while looking nothing like the late pop singer—because he finds the soft-spoken voice calming. Homer, having never seen nor heard the musician in his life, thinks “Michael” is the real deal and invites him home, much to the shock and disappointment of friends and family who thought they would have a chance to meet the King of Pop. Nevertheless, “Michael”/Leon successfully collaborates with Bart on a birthday song for the unhappy Lisa, leading the patient to accept who he really is.
While “Stark Raving Dad” is a polarizing episode—Eric Eisenberg of Television Blend named it the Simpsons’ best episode; the Toronto Star’s Ben Raymer considers it one of the three worst—Jackson’s performance was praised by critics, with IGN’s Robert Canning and Colin Jacobson of DVD Movie Guide noting the musician’s capacity to joke at his own expense. Jackson ranked #5 on IGN’s 2006 list of best Simpsons guest stars.
4 Johnny Cash – Space Coyote, “El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)”
While most of the figures on this list don’t really resemble their animated counterparts, they’re at least still playing the same species. The same can’t be said for country music legend Johnny Cash. In his lone appearance on the Simpsons, Cash didn’t take the form of his Man in Black persona but that of an angular-looking coyote. In the episode, Homer overdoes it once again, this time at a Springfield chili cook-off, where he accidentally overdoses on a pepper that is essentially half-chili, half-peyote. Stumbling around town in a psychedelic haze, he encounters Cash’s “space coyote,” a spirit guide who tells Homer to seek out his soul mate—planting a suspicion in the hallucinating husband’s mind that he wasn’t meant to be with Marge after all. Of course, Homer’s anxieties about his marriage are largely the product of drug-induced paranoia, and after a chaotic incident involving a lighthouse and a cargo ship laden with hot pants, he realizes that and Marge are on the same wavelength after all.
According to the episode’s DVD commentary, “(The Mysterious Voyage of Homer)” contained some of the series’ most complex sequences to date, namely during Homer’s prolonged psychedelic trip, which was handled entirely by animator David Silverman. It was also very positively reviewed—Crave Online’s Fred Topel called it the Simpsons’ all-time best episode—and Cash’s canine cameo was featured on best guest character lists by AOL and the Times.
3 Michelle Pfeiffer – Mindy Simmons, “The Last Temptation of Homer”
Being an occasional—okay, often—insensitive, drunken lout, Homer has occasionally acted inappropriately with women outside of his marriage, be it with a harem pants-wearing dancing girl or with up-and-coming country singer Lurleen Lumpkin, who he briefly managed in “Colonel Homer.” But those scenarios often came about because of Homer’s own ignorance rather than genuinely adulterous desires. Mindy Simmons, voiced by Michelle Pfeiffer (The Witches of Eastwick, Batman Returns), is the one major exception. A colleague at the nuclear power plant who rides a motorcycle to work and salivates in the presence of donuts, Mindy is, in terms of tastes and disposition, as far up Homer’s alley as any single person could be. When the two go to a business convention together, culminating in a candlelit dinner, Homer goes the closest he’s ever been to cheating on Marge. But thankfully, Homer’s love for his wife wins out—a decision that Mindy respects.
Both the episode and Pfeiffer’s performance received a generally positive reception upon its original airdate in late 1993, with the show itself ranking #10 on Entertainment Weekly’s list of the Simpsons’ top 25 episodes in 2003, and About.com’s Nancy Basile praising how Mindy’s deliberately brash character was an interesting contrast for the “elegant and beautiful” Pfeiffer. Mindy has also ranked highly on guest character lists compiled by EW, AOL and Total Film, and Metromix’s Brett Buckalew called Pfeiffer’s role the best in the series’ history.
2 John Waters – John, “Homer’s Phobia”
While transgressive filmmaker John Waters is better known for his directing and bizarre cinematic perspective than his acting, he is still quite a character in his own right. On the commentary for “Homer’s Phobia,” Waters said he instantly accepted the role of campy antique store owner John, who befriends the Simpsons when Marge attempts to sell what she thinks is a family heirloom (it turns out to be a whiskey flask in disguise). Homer finds John fun to be around, but he’s horrified when he learns the shop owner is gay and worries that he might inadvertently influence Bart’s sexual orientation. Homer’s desperate attempts to instill a proper sense of “masculinity” in his son backfire—funniest of all when he unintentionally brings Bart to a steel mill operated entirely by gay workers—and it’s ultimately John who comes to the rescue when a hunting trip goes sour. In the end, Homer accepts John for who he is and says he’ll do the same for Bart.
“Homer’s Phobia” was the first episode of the Simpsons to directly address LGBT issues, which had previously only been hinted at, albeit increasingly overtly, with the character of Mr. Smithers. The episode won both an Emmy for Outstanding Animated Program and a Gay and Lesbian Alliance Against Defamation award. The episode was overwhelmingly critically acclaimed and Waters’ character was named as one of the best guest characters by IGN, Entertainment Weekly and TV Guide.
1 Albert Brooks – Hank Scorpio, “You Only Move Twice"
Albert Brooks (Broadcast News, Finding Nemo, Drive) has voiced several characters on The Simpsons, one of the most recent being Russ Cargill, the villain of The Simpsons Movie, but he is perhaps best known for his one-episode stint as Globex Corporation head and Homer’s temporary boss, Hank Scorpio. Friendly, fast-talking and seemingly far nicer than Mr. Burns, Scorpio is initially the best boss the Simpson patriarch could have, greeting the family with a basket of papayas and letting Homer supervise his own team of technicians. Unbeknownst to Homer, however, Scorpio is a megalomaniac on par with the best Bond villains, threatening the United Nations, torturing and executing a Sean Connery-esque secret agent and building a super-laser. Regardless, he is genuinely sad to see Homer leave at the end of the episode—though Homer quits for personal reasons, still completely oblivious to Scorpio’s tyrannical scheme.
“You Only Move Twice” is considered one of the best episodes in the history of the Simpsons, with IGN and the Toronto Star’s Ben Raynor including it on various “best of” lists for the series’ run. Author Chris Turner, in his book Planet Simpson, highlighted Scorpio’s “paraxodical nature,” and IGN contributors Eric Goldman, Dan Iverson and Brian Zoromski placed the friendly supervillain at the top of their list compiling the top 25 Simpsons guest appearances.