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Artie Ziff

Artie makes his second appearance in the season thirteen episode "Half-Decent Proposal," rehashed by the writers as a "Silicon Valley billionaire." Artie makes his fourth appearance in "The Ziff Who Came to Dinner."

Director David Silverman modeled Artie's appearance and body language after his friend Michael Eisenberg, with whom he went to high school.

Bleeding Gums Murphy

Murphy first appeared in the season one episode "Moaning Lisa." In the episode, Murphy teaches Lisa how to express her sadness through music. Executive producer James L. Brooks had wanted to do an episode where Lisa was sad and she did not know why. (It was an idea the former-Taxi executive producer had wanted to use for the Alex Rieger character on that show.) "Moaning Lisa" co-writers Al Jean and Mike Reiss named Murphy after blues musician Blind Lemon Jefferson.

Murphy appears in the show's original full-length opening credits, created by animation director David Silverman, who inserted several characters into the credits who had been created up until the end of the first season.

Actor Ron Taylor voiced Murphy in "Moaning Lisa" and in "'Round Springfield." Jean and Reiss knew of Taylor from the TV series Wiseguy. The episode "Sweets and Sour Marge" was dedicated to Taylor, who died January 16, 2002, four days before the episode first aired. Musician Dan Higgins provided Murphy's saxophone playing in various episodes. Singer Daryl L. Coley voiced Murphy in "Dancin' Homer."

Herman

[[Image::Johnswartzwelder.jpg|left|thumb|Herman's facial appearance was modeled after
writer John Swartzwelder.]] Herman's facial design was modeled after that of Simpsons writer John Swartzwelder, who created the character.

Lindsey Naegle

Naegle first appeared in the season eight episode "The Itchy & Scratchy & Poochie Show." In that episode, she was named "Network executive." She appeared later in "Girly Edition" as the Channel 6 Executive. In the season ten episode "They Saved Lisa's Brain," she was introduced as Lindsey Naegle, then a member of the Springfield Chapter of Mensa, and has since become a recurring character.

The writers collectively based Naegle on a number of network executives that they have come into contact with while working on the show. Writer Matt Selman named the character, adopting her last name from Hollywood talent agent Sue Naegle, and choosing the character's first name because he thought that it sounded like the name of an annoyingly talkative woman.

The author of the book Planet Simpson, Chris Turner, called Naegle "an excellent allegory for the modern corporate age: you don't see through her because there's nothing else to see." Sun Media called Naegle one of their ten favorite Simpsons supporting characters.

Old Barber

The Old Barber first appeared in one of The Simpsons shorts, "Bart's Haircut," which aired as interstitials on the first three seasons of The Tracey Ullman Show (1987-1989). In the short, he cuts Bart's hair too low and then Bart tries several ways to disguise it. The Old Barber later appeared in the half-hour series in bit parts in the episodes "Simpson and Delilah," "Burns Verkaufen der Kraftwerk," "Radio Bart," "22 Short Films about Springfield," and "Lisa the Tree Hugger."

Castellaneta, who was chosen along with Julie Kavner to voice Homer and Marge respectively for the shorts, voiced the Old Barber in "Bart's Haircut" and in several of his appearances in the series, and based the voice on comedian Bob Elliott. Shearer voiced the character in his latest appearance in "Lisa the Tree Hugger." There was no model sheet used for the Old Barber until season seven, when Silverman had one created for Reardon, who directed "22 Short Films about Springfield."

Ruth Powers

Ruth Powers was voiced by actress Pamela Reed. She and her teenage daughter Laura (voiced by actress Sara Gilbert) were introduced in the season four episode "New Kid on the Block" moving in next-door to the Simpsons. A divorced single mother, Ruth soon becomes friends with Marge while Bart develops a crush for tomboyish Laura. Later, Ruth stars in "Marge on the Lam" in the fifth season where she and Marge go on the run from the police in a loose parody of the film Thelma & Louise. Ruth returned in the fourteenth season episode "Strong Arms of the Ma," revealed to have become a champion bodybuilder while in a Mexican prison. Aside from these three appearances, Pamela Hayden (the voice of Milhouse Van Houten) has voiced Ruth, who regularly appears in crowd scenes, a detail that Silverman was always calling for. Fifth and sixth seasons show runner David Mirkin said that Reed always gave great performances and that they should have used her more.