The 10 Best Guest Stars on ‘The Simpsons’ Who Didn’t Play Themselves

10 Beverly D’Angelo as Lurleen Lumpkin

First Appearance: “Colonel Homer,” Season 3, Episode 19

Who She Is: After Lurleen is discovered by Homer at a redneck bar, she becomes a big-time country singer and falls in love with him. After she makes her intentions known, Homer sells her contract.

Why She’s So Memorable: D’Angelo worked overtime to make the most of her appearance. In addition to singing all of her own songs, two of which she also wrote, she pitched jokes with the production team and improvised with Dan Castellaneta. 

Iconic Line-Reading: “Sorry, all my songs are up here: ‘I’m Basting a Turkey With My Tears,’ ‘Don’t Look Up My Dress Unless You Mean It,’ ‘I’m Sick of Your Lyin’ Lips and False Teeth.’”

9 Joe Mantegna as Fat Tony/Fit Tony

First Appearance: “Bart the Murderer,” Season 3, Episode 4

Who He Is: Underboss of the Springfield mafia

Why He’s So Memorable: Initially intended as a one-off character voiced by Sheldon Leonard, Mantegna managed to make Fat Tony such a funny, unique character that he’s appeared in a total of 40 episodes.

Iconic Line-Reading: “You have 24 hours to give us our money. And to show you we’re serious… you have 12 hours.”

8 Harvey Fierstein as Karl

First (And Only) Appearance: “Simpson and Delilah,” Season 2, Episode 2 

Who He Is: Assistant to the newly-haired Homer Simpson

Why He’s So Memorable: Karl hardly knows Homer, and yet, he is oddly supportive of him — from the moment he meets him until he sacrfices his own job to try and save Homer’s. Other than possibly just being a great assistant and amazingly selfless, we never quite understand why Karl acts like he does, but Fierstein’s performance makes us believe such a person could exist. The character almost returned in Season 14, but Fierstein turned down the part, keeping his character as a one-and-done.

Iconic Line-Reading: “I want you to say to yourself, ‘I deserve this. I love it. I am nature’s greatest miracle.’”

7 Glenn Close as Mona Simpson

First Appearance: “Mother Simpson,” Season 7, Episode 8

Who She Is: Homer’s rebellious political activist mother — who went into hiding when Homer was a kid after destroying Mr. Burns’ chemical warfare labs — briefly returns to Homer’s life, only to go into hiding again after being discovered by the FBI. She returned a few times thereafter, but eventually died in Season 19.

Why She’s So Memorable: Close, among the most accomplished actors to have appeared on The Simpsons, made a total of 11 appearances as Mona. Her chemistry with the other cast members — especially Castellaneta (as both her son Homer and her husband Abe) — is so pitch-perfect that it seems like she’s been working on the show the whole time it’s been on the air.

Iconic Line-Reading: “Remember, whatever happens, you have a mother, and she's truly proud of you.”

6 Danny DeVito as Herb Powell

First Appearance: “Oh Brother, Where Art Thou?,” Season 2, Episode 15

Who He Is: Homer’s more successful long-lost half-brother, whose story goes from riches to rags (and eventually riches again) after Homer becomes a part of his life.

Why He’s So Memorable: DeVito has a very recognizable voice that’s easy to connect to his own appearance, but he manages to create a character that comes across as nothing like him. Herb is the total opposite of Homer in almost every way, but his sad end in this episode — he goes bankrupt after a misguided attempt to invest all of his company’s money into Homer’s car design — still made you feel bad for him and caused the writers to revisit the character a season later to give him a happier ending.

Iconic Line-Reading: “Discarded pizza boxes are an inexpensive source of cheese.”

5 Jon Lovitz as Artie Ziff, Llewellyn Sinclair and Jay Sherman, among others

First Appearance: “The Way We Was,” Season 2, Episode 12

Who He Is/Why He’s So Memorable: Although he’s never appeared as himself in his 20 appearances on The Simpsons, the characters Lovitz has played — Homer and Marge’s high school classmate, Marge’s demanding musical director, the biggest loser of film critics, etc. — all play like some variation of him, and each role was typically written with him in mind. 

Iconic Line-Reading: “I am not an easy man to work for. While directing Hats Off to Hanukkah, I reduced more than one cast member to tears. Did I expect too much from fourth graders?”

4 Albert Brooks as Jacques, Brad Goodman and Hank Scorpio, among others

First Appearance: “The Call of the Simpsons,” Season 1, Episode 7

Who He Is/Why He’s So Memorable: Brooks has appeared in eight episodes, and none of the characters he’s played have returned for a second appearance (although fan-favorite Hank Scorpio was almost the antagonist of The Simpsons Movie; Brooks opted instead to play an original character). Brooks’ voice doesn’t vary greatly between characters, but each manages to have their own unique energy. He’s often allowed to improvise his lines, many of which end up in the final episodes, ensuring that any character he plays will be distinctively Albert Brooks.

Iconic Line-Reading: “Homer, on your way out, if you want to kill somebody, you would help me a lot.”

3 Kelsey Grammer as Sideshow Bob

First Appearance: “Krusty Gets Busted,” Season 1, Episode 12

Who He Is: Cultured and well-educated, “Sideshow Bob” Terwilliger spent several years as Krusty the Clown’s sidekick before being sent to jail for armed robbery. He had a second career as mayor of Springfield, among other endeavors, including an attempted murderer of *sinister voice* BART. SIMPSON.

Why He’s So Memorable: Initially hired as a one-off character by producer Sam Simon, who had worked with Grammer on Cheers, Grammer brought Bob to life through his charm, diabolical laugh and extensive knowledge of the complete works of Gilbert and Sullivan. He’s now appeared in more than 20 episodes.

Iconic Line-Reading: “By the way, I’m aware of the irony of appearing on TV in order to decry it, so don’t bother pointing that out.”

2 Marcia Wallace as Edna Krabappel

First Appearance: “Bart the Genius,” Season 1, Episode 2

Who She Is: Bart’s disillusioned and disgruntled elementary school teacher

Why She’s So Memorable: After appearing in 174 episodes, it’s hard to believe Wallace wasn’t ever officially considered a main cast member. The Bob Newhart Show actress began her stint as Krabappel in the second episode of the show and quickly made Edna her own, winning an Emmy for her performance in 1992. The show retired her character after her death in 2013.

Iconic Line-Reading: “Ha!”

1 Phil Hartman as Troy McClure, Lionel Hutz and Several One-Off Characters

First Appearance: “Bart Gets Hit by a Car,” Season 2, Episode 10

Who He Is: Hutz is your typical ambulance-chasing lawyer — and not a very good one at that. McClure is a B-movie actor who has been a “has been” for longer than he was ever a leading man, typically hosting any video or infomercial he can book.

Why He’s So Memorable: Hartman managed to make characters with very unlikable traits into fan favorites, performing their hilarious lines with a delivery only he could provide. The only missed opportunity — that Hutz never represented McClure in court. As with Wallace, the producers retired the characters after Hartman’s tragic death in 1998.

Iconic Line-Reading: “This is the most blatant case of fraudulent advertising since my suit against the film The Neverending Story” (Hutz); and “I’ve been reading a lot of scripts lately. You know, it’s a lot cheaper than going to the movies” (McClure).