The Simpsons has been on TV since December 1989, and it continues to be a hit. The show focuses on the Simpson family, which includes Homer, Marge, Bart, Lisa, and Maggie and their lives in the fictional town of Springfield, with a number of recurring characters for good measure.
Throughout the series’ run, there have been numerous video games, books, comic books, and The Simpsons Movie, which was released in 2007. In 1999, Time named The Simpsons the best television show of the 20th century. Over the decades it's been on the air, the show has welcomed numerous celebrity guest stars that helped make it the smash success it remains to this day.
Leonard Nimoy
In the episode “Marge vs. the Monorail,” a monorail salesman convinces Springfield to build what turns out to be an inoperable monorail system. To escape with the money he made from the fraud, the salesman hires Leonard Nimoy to be a celebrity guest at the monorail’s grand opening.
Nimoy’s guest appearance in this episode is hailed as one of the show’s best guest appearances, due to his performance as well as the episode’s well-crafted plot. Entertainment Weekly, in 2003, ranked the episode fourth in its ranking of the top 25 episodes.
Kelsey Grammer
Sideshow Bob, or Dr. Robert Terwilliger as he’s known professionally, first appeared in The Simpsons in “The Telltale Heart,” and would go on to appear in more than 40 episodes as Bart’s arch-nemesis. One of the most notable episodes featuring Sideshow Bob is the season 27 “Treehouse of Horror” episode where he finally (non-canonically) kills Bart. Although Sideshow Bob is portrayed as a villain, he shares characteristics of Kelsey Grammer’s other popular character, Dr. Frasier Crane from Cheers and Frasier, down to the fact that Sideshow Bob’s brother was voiced by David Hyde Pierce, who played opposite Grammer in Frasier.
Grammer has received various awards and accolades throughout his time as Sideshow Bob. At the 2006 Primetime Emmy Awards, Grammer won the award for “Outstanding Voice-Over Performance” for his work in the episode “The Italian Bob,” which remains a series highlight.
Phil Hartman
Phil Hartman was best known on The Simpsons for his performance as Troy McClure, who made his first appearance in the series’ second season and was featured as a recurring character. McClure was an actor who had a failing career and would appear mostly in infomercials and educational movies. In the episode, “A Fish Called Selma,” Troy appeared as the main character who marries Marge’s sister Selma to bolster his acting career. Meanwhile, Lionel Hutz, also voiced by Hartman, is described as an unethical “ambulance chaser” type lawyer who attempts to woo clients with gifts.
Hartman was originally brought on to provide voiceover as a one-time occurrence. However, he enjoyed working on the show so much that additional roles were written for him. Before Hartman’s death, he was planning on producing and starring in a live-action film centered on Troy McClure, which many Simpsons staffers had also expressed interest in. Upon Hartman’s murder in 1998, The Simpsons chose to retire his characters rather than seek out a replacement.
Michelle Pfeiffer
In the season 5 episode, “The Last Temptation of Homer,” Mr. Burns is forced by the Department of Labor to hire at least one female employee. Mr. Burns then hires Mindy, voiced by Michelle Pfeiffer. Homer is initially attracted by Mindy but dismisses his attraction as he feels that they don’t have anything in common. Homer is proven wrong when he sees that Mindy loves donuts and beer just as much as he does.
Before The Simpsons, Pfeiffer had never done any voiceover work for an animated character. Pfeiffer was instructed to not sound “flirty,” as producers wanted Dan Castellaneta (who plays Homer) and Pfeiffer’s performance to have subtlety. The result is one of the best celebrity appearances in the show's history as Homer's fidelity to Marge is tested due to his attraction to the charming Mindy.
Johnny Cash
In the season 8 episode, “El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)," Johnny Cash did a voice-over appearance as a mysterious spirit guide. In the episode, Homer overindulges at a chili cook-off and embarrasses Marge when he appears to get drunk. Homer burns his tongue on Chief Wiggum's chili infused with Guatemalan insanity peppers and tries to cool his tongue with beer.
Marge, thinking Homer got intentionally drunk, becomes angry and drives home without him. The peppers cause Homer to hallucinate, and he meets a coyote, who claims to be his spirit guide. The spirit guide tells Homer to find his soulmate, which causes Homer to wonder if Marge is meant to be his soulmate. Naturally, this all works out in the end, but when Johnny Cash asks you a question, you've got to at least consider it.
Meryl Streep
In the season six episode, “Bart’s Girlfriend,” Bart attends church and falls in love with Reverend Lovejoy’s daughter Jessica, played by Meryl Streep. Bart tries in vain to get her attention, but she ignores him. While Bart is trying his hardest to prove that he’s a good person, he finds out that Jessica secretly thrives on mischief, which she uses to get Bart in trouble.
During one church service, Jessica steals the money from the church’s collection plate, and leaves, leaving the empty plate with Bart. The congregation is led to believe that it was Bart who stole the money until Lisa leads them to discover it was Jessica who was guilty. Though things didn't work out with Jessica, the fact is that she and Bart had kind of a lot in common.
Glenn Close
For many years, Homer believed that his mother, Mona Simpson had died, which was a lie told by his father. In the season 7 episode, “Mother Simpson,” Mona returns to Springfield to reunite with a shocked Homer. During the 1960s, Mona was forced to go on the run from the law after destroying Mr. Burns’ biological warfare factory. Mona bonds with Homer, and with his family, but is forced to return to being on the run after being recognized by Mr. Burns.
Mona Simpson was voiced by Glenn Close in “Mother Simpson” as well as three other episodes. Her work on the series has been well-received with high praise. Close was revealed by Entertainment Weekly as one of the sixteen best series’ guest stars in 2008.
Dustin Hoffman
In the season 2 episode, “Lisa’s Substitute,” Lisa’s teacher, Ms. Hoover is diagnosed with Lyme disease and announces that she’s taking a leave of absence. In her place, Mr. Bergstrom will be the class’s substitute teacher. Lisa slowly falls in love with her substitute teacher's method of teaching and his friendly nature. While at a museum, Mr. Bergstrom senses that Lisa and Homer’s relationship is slowly falling apart, and he quietly encourages Homer to strive to be a more positive role model for Lisa. When Lisa discovers that Mr. Bergstrom is leaving for another job and that Ms. Hoover is returning, Lisa lashes out, especially at Homer. As Lisa says goodbye to Mr. Bergstrom at the train station, he hands her a note which simply says, “You are Lisa Simpson.”
Mr. Bergstrom was voiced by Dustin Hoffman, who at the time, was wary of working on an animated series. The entire cast flew to New York to work with Hoffman. Although the audio track came back to the producers with some of Hoffman’s audio too low, Yeardley Smith, who plays Lisa, stated on the commentary for the episode on the series’ season 2 DVD, that “she grew as an actress” while working with Hoffman.
Mark Hamill
In the season ten episode, “Mayored to the Mob,” the Simpsons attend a sci-fi convention where Mark Hamill is in attendance. After a riot breaks out endangering Mark and Mayor Quimby, Homer takes it upon himself to whisk them to safety. Quimby is impressed with Homer’s quick thinking and hires him as his new bodyguard, effectively firing his existing security. After Homer graduates from the bodyguard academy, he discovers that the mayor made a deal with the mafia to provide milk to the schools in Springfield; and discovers that the milk is rat milk. A confrontation erupts between the mayor and the mafia at a dinner theater performance, where Mark helps Homer save the mayor from being killed.
Mark Hamill agreed to participate in the episode only if he would be able to voice a character in addition to himself and stated that he preferred voicing the bodyguard instructor more than he did himself. Due to Hamill’s good-natured humor about his Star Wars past, various publications named Hamill as one of the Simpsons’ best guest stars.
Patrick Stewart
In the season six episode, “Homer the Great,” Homer discovers that Lenny and Carl are part of a secret society, called the Stonecutters. Homer discovers that he’s eligible to join since his father is a member as well. After Homer destroys the group’s sacred parchment, he is kicked out, until the other members notice that Homer has a birthmark in the shape of the group’s emblem. To the group, this signifies that Homer is the “Chosen One.”
Prior to Homer being the “Chosen One,” Patrick Stewart provided the voice for the group’s leader, named Number One. Of his time on the show as well as an appearance on Sesame Street, Stewart has said that both appearances “were perhaps the two most distinguishable bits of work that I’ve done in the US.” The show’s executive producer, David Mirkin, considered Stewart one of the show’s best guest stars due to his level of commitment to the character.