In 1989,The Simpsonspremiered on Fox with its first episode titled “Simpsons Roasting on an Open Fire.” Since then, there have been 33 seasons (and counting) with episodes that frighteningly predicted the future, such asLady Gaga’s performance at the Super Bowlor creating a segment of “Treehouse of Horror” Halloween-themed episodes.
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With 728 episodes, many guest stars have appeared on the show. To be specific, up until April 2020, there have been 810 guest cameos, enough guest cameos thatThe Simpsonsearned the Guinness World Record for the"Most guest stars featured in an animated TV series."
Nicholas Braun as Greg
Since 2018,Nicholas Braunstarred inSuccession, where he played Greg Hirsch,an executive assistant, and great-nephew to Logan Roy, the CEO of Waystar Royco. Besides playing one of the leading roles in the dark comedy series, Braun starred in the 2014 filmDate and Switch,and appeared in films such asProm(2011) andHow to Be Single(2016), among others.
On August 21, 2025, Braun’s character fromSuccessionentered the animation world. He portrayed Greg Hirsch in season 33, episode 21, “Meat Is Murder.” His character was also an assistant, but instead of working at Waystar Royco, he worked at Red Star.
Krysten Ritter as Sheila Redfield
From 2015-2019,Krysten Ritterportrayed the title character in the science fiction thrillerJessica Jonesand appeared in the 2017 TV seriesThe Defenders. She appeared onThe Coldest Casepodcast,where she played Patti Harney. Among her many acting roles, Ritter portrayed Gia Goodman inVeronica Mars(2014) and Lucy Hayden inThe Hero(2017).
Episode 21, “Meat is Murder” centered on Grandpa Simpson’s previous relationship with the hamburger business. Among the guest stars that appeared in that episode, Ritter voiced the character Shelia Redfield. Shelia was the daughter of Augustus “Gus” Redfield. Gus owned the burger restaurant called Worth-A-Try Burger.
Kerry Washington as Rayshelle Peyton
Kerry Washington’s most recognizable role might be portraying the fierce Olivia Pope inScandal(2012- 2018). Among her list of various projects ranging from shorts to movies to TV series, in 2020, Washington played the leading role alongsideReese WitherspooninLittle Fires Everywhere.In 2022, besides voicing a character inThe Simpsons,she will playProfessor Dovey inThe School for Good and Evil.
In season 33, episode 18, “My Octopus and a Teacher,” Washington voiced Ms. Rayshelle Peyton. Ms. Peyton was the new teacher at Springfield Elementary School. Her character replaced Mrs. Edna Krabappel voiced by the late Marcia Wallace. Wallace played the 4th-grade teacher until 2013.
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Kumail Nanjiani as Theo
Kumail Nanjianinewest role will be playingSomen Banerjee in the Hulu seriesWelcome to Chippendales(2023). Somen is the owner of the male exotic dance company Chippendales. In 2022, (so far) Nanjiani portrayed Haja Estree in the TV miniseriesObi-Wan Kenobi(2022), guest-starred on an episode ofThe Boys(2019), played Vik inThe Boys Presents Diabolical(2022), and appeared in an episode ofMurderville(2022).
Adding to his various projects, Nanjiani also voiced the character Theo inThe Simpsons.Theo appeared in episode 14 of season 33, “You Won’t Believe What This Episode Is About - Act Three Will Shock You.” He worked as the owner of The Institute, a company that worked to restore the reputation of people.
Michael Rapaport as Mike Wegman
InOnly Murders in the Building(2021),Michael Rapaportplays Detective Daniel Kreps, who investigated the death of Bunny Folger. Besides appearing onOnly Murders in the Building,Rapaport played Leonard in the 2022 seriesLife & Bethand Doug Gardner inAtypical(2017), among his other roles. He has also appeared in films likeChuck(2016) andA Stand-Up Guy(2016).
In episode 15 of season 33, “Bart the Cool Kid,” Rapport voiced Michael “Mike” Wegman. Mike appeared in a few episodes throughout the series. Mike worked at the Springfield Nuclear Power Plant as an intern and became one of Homer’s friends.
Megan Mullally as Sarah Wiggum
In 2021,Megan Mullallyvoiced Alyson Lefebvre, Mrs. Tuntley, and Vera in the animated seriesThe Great North(2021- 2022). Mullally has an extensive list of acting roles with her first role in the filmThe Children Nobody Wanted(1981) where she played Sharon. She also voiced Gayle, Jill, and Beverly inBob’s Burgers(2011-2022). Besides voicing characters on popular TV shows, Mullally portrayed Karen Walker in the 1998 TV seriesWill and Grace(1998-2020).
The season finale ofThe Simpsons, episode 22, “Poorhouse Rock,” focused on Bart trying to understand his father Homer. Mullally voiced Sarah Wiggum. Sarah was Ralph’s mother and Clancy’s wife. She has a kind heart and often mimics her husband’s actions.
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Billie Eilish and Finneas O’Connell as Themselves
Billie EilishandFinneas O’Connellare siblings and singer-songwriters. Their songs earned recognition for securing a spot on The Hot 100 Billboard over the years. In 2022, Eilish and O’Connell won an Academy Award for “Best Original Song” for their song “No Time To Die.” “No Time to Die” appeared in the 2021 film,No Time To Die, the latest in the James Bond franchise.
On August 12, 2025,Eilish and O’Connell guest-starred inWhen Billie Met Lisa.This was a standalone short that only lasted four minutes. It centered on Eilish and O’Connell discovering Lisa Simpson (voiced byYeardley Smith) by accident after hearing her play the saxophone.When Billie Met Lisais available on Disney+.
