Since its inception, the bulk of the voice work onThe Simpsonshas been split between six actors:Dan Castellaneta,Yeardley Smith,Nancy Cartwright,Julie Kavner,Hank AzariaandHarry Shearer. Other actors voice a few of the regular recurring characters, likePamela Hayden’s Milhouse Van Houten or the lateMarcia Wallace’s Edna Krabappel. Then there’s the celebrity guests who voice characters that have had appearances throughout the 34 seasons of the show, includingJoe Mantegna’s Fat Tony andKelsey Grammer’s Sideshow Bob.

One actor, though, made such an indelible mark on the series before his untimely death in 1998 that his status as one of theSimpsons’greatest voice actors is cemented in history:Phil Hartman. His characters are oft-quoted fan favorites to this day: as many as 20 separate characters, all of which he imbued with his own perfect comic timing and delivery. His association with these characters runs so deep, in fact, that most, if not all, of his characters have not been used on the show since.

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Hartman was a no-brainer for a guest star on the show. In his time onSaturday Night Livebetween 1986 and 1994, Hartman did impressions of over 70 characters, includingEd McMahonandBarbara Bush. His first appearance was designed to be a one-off as Springfield lawyer Lionel Hutz in the 1991 episode “Bart Gets Hit by a Car.” Reportedly, he really enjoyed working onThe Simpsons, and the staff enjoyed working with him as well. This led to additional parts being written specifically for him. CreatorMatt Groeninghimself admitted thatHartman “nailed the joke every time”, producing the “maximum amount of humor.“Of the many characters he played on the show, the three most commonly associated with Hartman, and the most beloved, are Lionel Hutz, actor Troy McClure, and snake oil salesman Lyle Lanley.

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Lionel Hutz was an incompetent Springfield lawyer who first appeared in Season 2, a character not too far removed from Hartman’sSNLcharacter, Unfrozen Caveman Lawyer. He was repeatedly hired by the Simpsons family because he was affordable. His statusasa lawyer, though, is suspect at best, as he claims that he graduated from Princeton Law School (Princeton has not had a law school since the 19th century), and named his legal practice “I Can’t Believe It’s A Law Firm!” Somehow Hutz managed to win several cases for the Simpsons, including Homer’s (Castellaneta) case against Captain McCallister (Azaria) and The Frying Dutchman restaurant over its “All You Can Eat” offer in the 1992 episode “New Kid on the Block.” In the episode, Homer goes to the restaurant for the offer and eats “all the shrimp and two plastic lobsters” before getting kicked out, even though he was still hungry. Hutz takes the case, saying, “Mr. Simpson, this is the most blatant case of fraudulent advertising since my suit against the movie,The Neverending Story!” Hutz also sued Krusty the Clown (Castellaneta) on behalf of Bart (Cartwright), who got appendicitis after eating a piece of jagged metal, a prize in his Krusty-O’s. Bart was given $100,000 in compensation, of which Hutz took $99,500

A long-running joke on the Simpsons featured Hartman’s has-been Hollywood actor Troy McClure showing up in educational videos and infomercials and listing previous works similar to the current project: “Hi, I’m Troy McClure. You may remember me from such medical films asAlice Doesn’t Live AnymoreandMommy, What’s Wrong With That Man’s Face?” The highly popular McClure, who wasranked #1 on IGN’s list ofThe Simpsons' Top 25 Peripheral Characters, was prominently featured in the classic episode “A Fish Called Selma.” McClure, whose career went downhill after a rumored fish fetish, began a relationship with Selma (Kavner) at the prompting of his agent, who noted that his career could be revived by being seen with a “human woman.” The advice works, landing him a leading role in a musical version of the filmPlanet of the ApescalledStop the Planet of the Apes, I Want to Get Off!To further help his career, his agent suggests that he marry Selma, which Selma accepts despite knowing it’s a ruse. But when the agent suggests McClure had a child with her, Selma calls the marriage off. Fun fact: McClure was the second Hartman character to be married to Selma, as Lionel Hutz was briefly married to her offscreen. Both names are referenced in Selma’s hyphenated surname Bouvier-Terwilliger-Hutz-McClure-Discotheque-Simpson-D’Amico.

Hartman’s most memorable one-off character has to be as conman Lyle Lanley in 1993’s “Marge vs. the Monorail.” The episode begins with Mr. Burns (Shearer) fined by the EPA for $3 million for dumping nuclear waste in a Springfield park. A town meeting is held to decide how the money will be spent, and Marge convinces them to repair Main Street. Unfortunately, a salesman named Lyle Lanley shows up and leads a song-and-dance routine that convinces the town to build a monorail. Suspicious Marge discovers that Lanley intends to run off with money from the project, leaving them with a defective train and a randomly selected Homer as its engineer.

News of Hartman’s death in 1998 hit the cast and crew ofThe Simpsonshard, the first member of their close-knit group to pass. The producers of the show decided not to find a replacement for Troy McClure or Lionel Hutz, opting to retire the characters outright. It was a display of respect, and an admission that what Hartman brought was impossible to replace. It’s no coincidence that the golden age of the show aligns with the short time Hartman was a key contributor. Even thoughThe Simpsonshas endured and delivered other beloved episodes since, there will always be a hole where Hartman used to be.