39. Buzz Aldrin
Episode: “Deep Space Homer”
It isn’t often that we get a prestigious member of the scientific community on the show. It comes in handy when you want to portray the true horror of opening a bag of potato chips in zero gravity.
“Watch it, they’re ruffled!”
38. Sara Gilbert as Laura
Episode: “New Kid on the Block”
A longtime Roseanne vet, Gilbert had experience being the type of girl next door who wears an army jacket. She brings out a lovestruck side of Bart that we don’t see very often, especially with older women. No, we don’t count that fake affair with Edna Krabbapel.
Bart: “How can you like that guy?”
Laura: “I dunno. Maybe because he’s an outlaw. You know that dead body they found behind the mayor’s house?”
Bart: “Jimbo killed him?”
Laura: “No. But he poked him with a stick.”
37. Beverly D’Angelo as Lurleen Lumpkin
Episode: “Colonel Homer”
You’d probably recognize her as the hot mom in National Lampoon’s Vacation movies, but D’Angelo has a pretty nice set of pipes. She actually wrote and sang Lurleen’s songs in the episode; maybe if Lurleen was that talented, she would’ve aimed her romantic reticule higher than Homer.
Homer: “Guess what, Lurleen. I got you a gig on TV!”
Lurleen: “Oh, Homer! You’re as smart as you are handsome!”
Homer: “Hey! ...Oh, you meant that as a compliment.”
36. Conan O’Brien
Episode: “Bart Gets Famous”
After jetting out of The Simpsons writers’ room, Conan spared no time in coming back to guest star on the show and rub it in everyone’s face. Whatever happened to that guy?
“Sit perfectly still. Only I may dance.”
35. Harvey Fierstein as Karl
Episode: “Simpson and Delilah“
Before tackling the issue outright with John Waters, The Simpsons made television history with the first male-on-male romantic kiss ever broadcast. More than just a stunt, Fierstein lent credibility to Karl’s character, and even some ambiguity.
Karl: “You don’t belong here. You’re a fraud and a phony, and it’s only a matter of time until they find you out.“
Homer: “Gasp! Who told you?“
Karl: “You did. You told with me with the way you slump your shoulders, the way you talk into your chest, the way you smother yourself in bargain-basement lime-green polyester.“
34. James Earl Jones as the Narrator
Episode: “Treehouse of Horror I”
There’s only one man who can give Edgar Allen Poe’s work the gravitas it deserves, and since Gilbert Gottfried wasn’t available, James Earl Jones sufficed. Though Jones doesn’t play an actual character in the Simpson-ized version of “The Raven,” his voiceover was integral, and frankly, unforgettable.
“Once upon a midnight dreary, while I pondered, weak and we—”
Well, you know the rest.
33. Jon Lovitz as Artie Ziff
Episode: “The Way We Was”
Lovitz has played several of Springfield’s citizens, but the best (and also just the worst) would have to be Artie Ziff, the dorky prom king with an intense libido. In this flashback episode, Homer has to woo Marge away from the technically superior Ziff; Lovitz is so adept at playing slimeballs that you actively root against him in addition to rooting for Homer.
“Marge, I would appreciate it if you didn’t tell anyone about my ‘busy hands.’ Not so much for myself, but I am so respected, it would damage the town to hear it.”
32. Ron Taylor as Bleeding Gums Murphy
Episode: “‘Round Springfield”
Only appearing in a couple episodes, Bleeding Gums Murphy is one of the most enduring side characters in Simpsons lore. Maybe it was the character’s early death, or Taylor’s gruff but accurate approximation of what everyone thinks every jazz musician sounds like. When Taylor himself passed away, it only solidified Bleeding Gums’ place in the echelon of The Simpsons.
BG: “My friends call me “Bleeding Gums.””
Lisa: “Ew. How did you get a name like that?”
BG: “Well, let me put it this way: you ever been to the dentist?”
BG: “Not me. I suppose I should go to one, but I got enough pain in my life as it is.”
31. Adam West
Episode: “Mr. Plow”
Before Family Guy came and stretched this cameo into a full-blown recurring character, West’s self-deprecating appearance delighted Batman fans young and old. Since no one had seen his failed pilot Lookwell except know-it-all comedy nerds, his distinctly post-modern sense of humor was a revelation to most.
“Michelle Pfeiffer? Ha! The only true Catwoman is Julie Newmar, Lee Meriwether, or Eartha Kitt. And I didn’t need molded plastic to improve my physique. Pure. West.”
30. Barry White
Episode: “Whacking Day”
If anyone could pull off the fake guest star by way of pre-recorded music, it would be Barry White. He doesn’t stoop to that level when it came to protest Springfield’s cruel snake-killing holiday, instead delivering some of the goofiest lines ever said in a really sexy way.
“I love the sexy slither of a lady snake.”
29. Kathleen Turner as Stacy Lovell
Episode: “Lisa vs. Malibu Stacy”
Another guest star with an incredible voice, Turner sounds like she was chain smoking in the womb. She’s perfect as the bitter recluse who created the Malibu Stacy doll, and an excellent cynical foil to Lisa’s unending optimism.
“I may have had things in common with Stacy at the beginning, but thirty years of living her lifestyle taught me some very harsh lessons. Five husbands: Ken, Johnny, Joe, Dr. Colossus, Steve Austin…”
28. Jack Lemmon as Frank Ormand
Episode: “The Twisted World of Marge Simpson”
Here’s a weird one. Lemmon plays a dopey pretzel salesman, not unlike his character in the film version of Glengarry Glen Ross. At the same time, another Simpson character called Gil is also based on Lemmon’s Glengarry character, but is voiced by regular cast member Dan Castellanetta. If the two met, imagine what would happen! Probably nothing, but it’s interesting to think about. It isn’t, is it? Okay, we can stop here.
“It’s not only not bad—it’s not bread. ‘Knot bread,’ you get it? See?”
27. Stephen Hawking
Episode: “They Saved Lisa’s Brain”
Everyone knows what Hawking’s computerized voice sounds like, so it wouldn’t have been hard to just plug him into Springfield’s Mensa program without getting him in the studio. Incredibly, that’s exactly what they did. It probably didn’t make a real difference in the performance on the show, but it’s good for getting bumped up a few places.
“I wanted to see your utopia, but now I see it is more of a Fruitopia.”
26. Hank Williams Jr.
Episode: “The Last Temptation of Krust”
There are a lot of guest stars in “The Last Tempation of Krust,” but Williams blows them all away from offscreen. He’s the voice of the Canyonero, the ridiculous SUV that Krusty the Klown ends up hocking for. Williams’ country-twanged jingle is the catchiest song this side of the monorail.
“She blinds everybody with her super-high beams/She’s a squirrel-crushin, deer-smackin’ drivin’ machine!/Canyonero!-oh whoa!/Canyonero!”
25. Michelle Pfieffer as Mindy
Episode: ‘The Last Temptation of Homer”
Possibly the most alluring of all of Homer’s near-misses with adultery, Mindy is essentially a buxom female version of the man himself. Obviously Homer decides to stick with Marge, but some lucky guy in Springfield is going to end up with a donut-loving babe who sounds like Michelle Pfieffer when she drools.
Mindy: “Homer? I got a really wicked idea that could get us into a lot of trouble.”
Homer: “Oh, Mindy… we have to fight our temptation.”
Mindy: “No, Homer, let’s do it. Let’s call room service!”
24. Mickey Rooney
Episode: “Radioactive Man”
Rooney’s appearance in this episode was a little bit like Adam West’s, but somehow even was better. Maybe it was the inflated sense of himself and his box office records. Maybe it was the uplifting speech he gave to Milhouse in an effort to get him to come back to a movie set. But really, it’s probably just him in the Fallout Boy costume saying “Jiminy Jillickers!”
“Jiminy Jillickers! Jiminy Jillickers! Jiminy Jillickers!”
23. Tito Puente
Episode: “Who Shot Mr. Burns?”
Several musicians have tweaked their work or even created music specifically for the show, but Tito Puente’s Emmy-nominated “Senor Burns” might trump them all. Bless his heart, he even managed to bring back one of Bart’s old catchphrases.
22. Rodney Dangerfield as Larry Burns
Episode: “Burns, Baby Burns”
In basically everything he’s ever been in, Rodney Dangerfield plays himself. It’s just that in this episode, he also plays Mr. Burns’ long-lost son. We get all the trademark Danger-isms, all wrapped inside a Mr. Burns-heavy storyline. That’s a combo that deserves respect.
“Wow, this guy is loaded. I mean sheesh. I’ve never seen a guy with a walk-in mailbox. I mean he’s rich. Hey, who am I talking to?”
21. Johnny Cash as Homer’s Spirit Coyote
Episode: “El Viaje Misterioso de Nuestro Homer”
If you got Johnny Cash to be on your television show, that’s a career-defining moment. If you got Johnny Cash to be on your television show as a mystical/hallucinogenic coyote, complete with recorded growling noises, you should probably just retire on top.
Coyote: “Find your soulmate, Homer. Find your soulmate.”
Homer: “Where? Where?”
Coyote: “This is just your memory. I can’t give you any new information.”