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In 1989, The Simpsons premiered 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 as Lady Gaga‘s performance at the Super Bowl or creating a segment of “Treehouse of Horror” Halloween-themed episodes.
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 that The Simpsons earned the Guinness World Record for the “Most guest stars featured in an animated TV series.”
Nicholas Braun as Greg
Since 2018, Nicholas Braun starred in Succession, 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 film Date and Switch, and appeared in films such as Prom (2011) and How to Be Single (2016), among others.
On May 15, 2022, Braun’s character from Succession entered 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 Ritter portrayed the title character in the science fiction thriller Jessica Jones and appeared in the 2017 TV series The Defenders. She appeared on The Coldest Case podcast, where she played Patti Harney. Among her many acting roles, Ritter portrayed Gia Goodman in Veronica Mars (2014) and Lucy Hayden in The 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 in Scandal (2012- 2018). Among her list of various projects ranging from shorts to movies to TV series, in 2020, Washington played the leading role alongside Reese Witherspoon in Little Fires Everywhere. In 2022, besides voicing a character in The Simpsons, she will play Professor Dovey in The 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.
Kumail Nanjiani as Theo
Kumail Nanjiani newest role will be playing Somen Banerjee in the Hulu series Welcome 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 miniseries Obi-Wan Kenobi (2022), guest-starred on an episode of The Boys (2019), played Vik in The Boys Presents Diabolical (2022), and appeared in an episode of Murderville (2022).
Adding to his various projects, Nanjiani also voiced the character Theo in The 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
In Only Murders in the Building (2021), Michael Rapaport plays Detective Daniel Kreps, who investigated the death of Bunny Folger. Besides appearing on Only Murders in the Building, Rapaport played Leonard in the 2022 series Life & Beth and Doug Gardner in Atypical (2017), among his other roles. He has also appeared in films like Chuck (2016) and A 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 Mullally voiced Alyson Lefebvre, Mrs. Tuntley, and Vera in the animated series The Great North (2021- 2022). Mullally has an extensive list of acting roles with her first role in the film The Children Nobody Wanted (1981) where she played Sharon. She also voiced Gayle, Jill, and Beverly in Bob’s Burgers (2011-2022). Besides voicing characters on popular TV shows, Mullally portrayed Karen Walker in the 1998 TV series Will and Grace (1998-2020).
The season finale of The 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.
Billie Eilish and Finneas O’Connell as Themselves
Billie Eilish and Finneas O’Connell are 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 April 22, 2022, Eilish and O’Connell guest-starred in When Billie Met Lisa. This was a standalone short that only lasted four minutes. It centered on Eilish and O’Connell discovering Lisa Simpson (voiced by Yeardley Smith) by accident after hearing her play the saxophone. When Billie Met Lisa is available on Disney+.
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