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He also occasionally appears to serve as a prosecutor. Unlike Lionel Hutz or Gil Gunderson, he is competent, although not necessarily ethical. He has served as Mr. Burns' head lawyer, helping him out with threats of the Power Plant closing down and of Burns losing his money.

In "Little Girl in the Big Ten", Pommelhorst decides that because of the oath Pommelhorst took on Xena, Pommelhorst has to fail Lisa but decides to let her make it up by taking private lessons. In "My Fair Laddy", Pommelhorst took a leave of absence to get a sex-change operation and will return as "Mr. Pommelhorst" , the new shop teacher and is replaced with Coach Krupt. Despite this, the character has appeared in later episodes as a woman. Arnie Pye is a disgruntled, somewhat eccentric helicopter traffic reporter for Springfield's KBBL-TV . He dislikes pompous anchorman Kent Brockman, with whom he often gets into arguments on the air.
Agnes Skinner
Quimby scolds her for lying about her graduating from "typing school". In "Smoke on the Daughter", she appears pregnant, and Quimby believes he may be the father. Martin "Gareth" Prince Sr. is the father of Martin Prince, and husband of Martha Prince. He is a stockbroker in Springfield and was shown bringing his son to work on "Go To Work With Your Parents Day", where Martin made over $1 million trading soy futures (and subsequently lost all but $600). He appears to be a nerd much like his son, and has a slight lisp.
Stampy also attacks a bear in the final scene of "The Fat and the Furriest", but then the bear fights back by hitting Stampy on the head with a club several times, much to Stampy's dismay. Stampy also appears in The Simpsons Movie, where he cracks the dome that covers Springfield, prompting the government's drastic decision to implement Option No. 4 as a solution to the Springfield Problem. At one point in the movie, the Simpsons' house is completely destroyed after being sucked into a sinkhole in their backyard.
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According to "Who Shot Mr. Burns? ", Kent Brockman does not like Dave Shutton and thinks he is unprofessional. Dave Shutton (voiced by Harry Shearer) is a reporter for The Springfield Shopper. Writer John Swartzwelder named Shutton after a friend of his.
In the episode "Replaceable You", it is implied that Chalmers wears a toupee (according to Dolph's science project, a toupee detector). Richard is a gray-haired student at Springfield Elementary School and is one of Bart's friends. He is usually seen with his best friend Lewis and has a leather jacket and a shirt with a small diamond embroidered on the center. Richard appears frequently in scenes involving the Springfield children, and in the early seasons was often involved with mischief.
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Booberella's name alludes to Vampirella (Forrest James Ackerman's comic book vampire character) and to the 1968 cult film Barbarella, which stars Jane Fonda in the title role. In "Treehouse of Horror XXIII" , Bart time-travels to 1974 and happens upon Marge, who is still a high school student. After he warns her not to marry Homer, Bart returns to 2012 and finds that Marge has married Artie, with Bart now named Bartie Ziff, and having inherited Artie's curly hair. Marge leaves Artie after she instantly falls in love with a host of time-traveling Homers. She says seeing them made her realize she had married the wrong man.
He is a spoof of actor Jack Lemmon's portrayal of Shelley Levene in the 1992 film adaptation of the play Glengarry Glen Ross. (Lemmon himself voiced a character similar to Levene in the eighth season episode "The Twisted World of Marge Simpson".) Show runner Mike Scully said that the writers thought that Gil would be "a one-shot thing". "Castellaneta was so funny at the table read doing the character we kept making up excuses in subsequent episodes to put him in", Scully said. Writer Dan Greaney said it was a great take-off on Levene to make Gil more desperate than he was. Even so, the writers like to write Gil with "a little bit of the old sparkle" left in him. Grimes, Sr. , occasionally referred to as "Grimey" much to his displeasure, was a 35-year-old everyman and consummate professional who had struggled through a lifetime of hardship.
Dr. Marvin Monroe
Her mother is an Italian who abused Milhouse whenever he spoke English. In "Lemon of Troy", it is revealed that Luann originally came from Springfield's bitter rival, Shelbyville, but moved to Springfield early in life, presumably with her father, as her mother remained in Italy. In "A Milhouse Divided", it is revealed she has a sister , but whom we never meet.

He first appears in the second season in "One Fish, Two Fish, Blowfish, Blue Fish". Actor George Takei originally voiced Akira in "One Fish, Two Fish, Blowfish, Blue Fish". Since Akira's speaking role in "When Flanders Failed" where the character is depicted as a karate teacher, Hank Azaria has voiced the character, doing an impression of Takei for the voice. Takei returned to voice Akira in season 24's "What Animated Women Want". The character's name is a reference to the Japanese director Akira Kurosawa. Azaria does a Charles Bronson impression for the voice.
He is shown as a very strict bureaucrat, and has little compassion for the prisoners under his control. He releases Crowley into Marge's care after she vouches for him. The Vanderbilts are an elderly rich couple who are frequently shocked by Homer Simpson's antics. They first appear in "Saddlesore Galactica" where Mr. Vanderbilt breaks his monocle after being shocked. In "Homer vs. Dignity", Mrs. Vanderbilt is shocked by Homer's antics twice. In "The Frying Game", Mrs. Vanderbilt is shown as friends with Mrs. Bellamy, Mrs. Glick, and Agnes Skinner.
Luigi Risotto (voiced by Hank Azaria) is the proprietor of Luigi's, a Springfield Italian restaurant. He is a parody of the "Italian pasta/pizza chef" stereotype (and in fact is on a bowling team called "The Stereotypes", along with Cletus Spuckler, Captain Horatio McCallister, and Groundskeeper Willie), but seems to be aware of his status as a stock character. He is polite to his customers and treats them with respect when they order and then loudly insults and belittles them to his cook Salvatore, fully aware that they can hear him from the kitchen.
Martin Sr. was also one of the fathers who traveled in Ned Flanders's RV to locate their sons in Shelbyville. Lurleen Lumpkin (voiced by Beverly D'Angelo in "Colonel Homer", Doris Grau in "Marge vs. the Monorail") is an aspiring country singer who is initially managed by Homer in "Colonel Homer". Homer discovers her in a redneck bar in the middle of nowhere and is amazed by her voice.

It turned out, though, that Sideshow Bob faked the whole thing in another elaborate plot to kill Bart. Mr. Burns' Lawyer, also known as The Blue-Haired Lawyer , is Springfield's most prominent and powerful lawyer. He first appeared in the second season episode "Bart Gets Hit by a Car". He is known for his blue hair, authoritarian nature and nasal New York City accent.
While in her extrovert "Belladonna" personality she displayed bisexual tendencies, inviting Marge to join her and Timothy's tryst - albeit unaware that it's Marge's voice she can hear. Agnes's first name was revealed in the seventh season episode "Bart the Fink". Before that, the character was known as "Mrs. Skinner". In the beginning of the series, the writers made several references to Agnes and Seymour's unhealthily close relationship as similar to that of Norman Bates and his mother.
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