58 – 57. George Carlin and Martin Mull as Seth and Munchie
Episode: “D’ohin in the Wind”
Most guest stars exist to move along the plot or to deliver a quick joke, but it’s rare to see them facilitate any kind of character development. Seth and Munchie offer a window into the groovy world Homer missed while his mother was off being an environmental radical. It helps that Carlin and Mull are totally believable as stoner uncles.
Seth: “We used to have a bus.”
Munchie: “In a way, the ‘60s ended the day we sold it. December 31st, 1969.”
56. Ringo Starr
Episode: “Brush with Greatness”
It’s funny to think that the least-popular Beatle is featured the most prominently in a Simpsons episode (though it does make a sad amount of sense). There’s something sweet in the sincerity of the joke about a man in the biggest band in the world still going through his back catalog of fan mail. You really believe that if any of them would actually do that, it’s Ringo.
“Dear Sally. In response to your letter of December the 12th 1966, me favourite colour is blue, and me real first name is Richard. Thanks for the snapshot. You’re a real cute bird. Love, Ringo. PS: Forgive the lateness of my reply.”
55 – 53. Spinal Tap
Episode: “The Otto Show”
It was only a matter of time before series regular Harry Shearer pulled in Christopher Guest and Michael McKean to reunite Spinal Tap, the best bad band that ever was. Though the animated format loses some of the improvisational fun of the classic movie, the guys still get some good licks in.
“I can’t think of anyone who’s benefited more from the death of communism than us.”
52. David Hyde Pierce as Cecil Terwiliger
Episode: “Brother from Another Series”
In another no-brainer crossover, Pierce played upon his inexorable link to Kelsey Grammer, his brother in Frasier. How convienent it was that Sideshow Bob never mentioned he had a brother, Cecil. Coincidence aside, the pair brought years of experience and a natural chemistry to what would otherwise be just another wacky Sideshow Bob plot.
Bart: “Guess who?”
51. Robert Goulet
Believe it or not, before his image was eternally tarnished by a series of Will FerrellSNL sketches, Goulet had a somewhat positive image. Who could hate a guy who sang “Jingle Bells, Batman Smells” at a makeshift casino for kids?
Goulet: “Are you sure this is the casino? I think I should call my manager.”
Nelson: “Your manager says for you to shut up!”
Goulet: “Vera said that? Hmph.”
50. Pamela Reed as Ruth Powers
Episode: “Marge on the Lam”
You might remember Reed as That One Lady From That Thing, or probably just this episode. She used that unassuming charm as the longtime neighbor, first-time plot point Ruth, who gave Marge a brief Thelma and Louise adventure.
“I should get home to my daughter before that naked talk show comes on.”
49. Neil Patrick Harris as “Bart”
Episode: “Bart the Murderer”
The only stunt casting more terrible and perfect than Dennis Franz as Homer is a young Neil Patrick Harris as Bart. What’s next? Elle Fanning as Lisa? Katey Segal as Marge? Maybe if we say it enough, it’ll magically appear on basic cable.
‘Tony’: “Bart, I’m scared. Let’s get out of here.”
‘Bart’: “Shut up! Where do you want it, Skinner?”
‘Skinner’: [spits on him]
‘Bart’: “Not smart.” [pumps him full of lead]
48. Alex Trebek
Episode: “Miracle on Evergreen Terrace”
Before his infamous mustache-shave, Trebek gave a peek inside the seedy underbelly of Jeopardy. It’s not pretty if you lose.
Alex Trebek: “Aren’t we forgetting something, Marge? You were down fifty-two hundred dollars.”
Marge: “But Mr. Trebek—”
Alex: “I asked you before the game if you knew the rules and you said you did. Judges?”
47. Jay Mohr as Christopher Walken
Episode: “Insane Clown Poppy”
Christopher Walken has never been on The Simpsons, but the producers got something arguably better: Mohr’s Walken impression. In the show we only get a few lines of “Walken” reading Goodnight, Moon. We’d love to see the full thing show up on iTunes someday.
“Please, children, scooch closer. What have I told you… about the scooching?”
46. Ernest Borgnine
Episode: “Boy Scoutz N’ the Hood”
Even in his earlier years, Borgnine was already America’s grandpa, so it made sense for him to play himself as a boy scout leader. Somehow he fits into Springfield more than most guest stars. Maybe it’s the paunch.
“Hiya! I’m sure you kids know me best as Sergeant Fatso Judson in From Here to Eternity.”
45. George Harrison
Episode: “Homer’s Barbershop Quartet
Paul McCartney is more famous, and Ringo has more screen time, but there’s something to be said for facilitating one of The Simpsons’ all-time greatest lines.
George: “Hello, Homer! I’m George Harrison.”
Homer: “Oh my God. Oh my God! Where did you get that brownie?”
George: “Over there. There’s a big pile of them.”
44 – 40. The Cast of Cheers
Episode: “Fear of Flying”
It’s weird to think that when sitcoms end, the lives of the characters keep going, and can even get worse. This is illustrated in the short but impressive cameoganza from Ted Danson, Rhea Perlman, Woody Harrelson, John Ratzenberger and George Wendt. In the segment, Homer steps into the famous bar to find that Norm is a raging, violent alcoholic who has finally lost it. Homer left quickly because he didn’t want to live in that world, and neither do we.
Norm: “Woody, gimme a beer.”
Woody: “I think you had enough, Mr. Peterson. My chiropractor says I can’t carry you home anymore.”
Norm: “Just gimme another beer, you brain dead hick! I’ll kill ya! I’ll kill all of ya!”