After being renewed for another two seasons, it’s hard to imagine which celebrities haven’t been featured inThe Simpsons. Over the years many iconic figures from musicians to actors and even Prime Ministers have featuredin the longest-running animated series, but there are times when celebrities add something different to the mix and play a written character.
The show hashad recurring voice actorsplay some of the most iconic characters such as Sideshow Bob (Kelsey Grammer), Fat Tony (Joe Mantegna), and Edna Krabappel (Marcia Wallace), but some of Hollywood’s biggest starshave only appeared once or twicethroughout the entire series. How little their appearances may be in the over 700 episode timeline ofThe Simpsons,the impact these celebrity guests have hadon the show on benefited both comedy and emotional levels.

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Patrick Stewart
Following on from the end ofStar Trek: The Next Generationand hisiconic role as Captain Picard, Patrick Stewart found himself in the hilariousSimpsonsepisode,Homer The Great. After Homer joins The Stonecutters, a freemasonry-style group, he meets Number One who is the leader of the Springfield Stonecutters. Stewart portrays Number One whose name is a reference toStar Trekwith Number One being the name Picard would give to his second in command, William Ryker. Stewart hasplayed a variety of strange rolesover the years, butSimpsonswriters praised his commitment and overall dedication to the role of Number One.
The character had a variety of Stewart’s acting abilities from a leader to dramatic stage-style performing. The episode as a whole is considered one of the best and no doubt for its great storytelling of one-upping and parody of closed societies, but Stewart’s acting performance drew attention away from Homer’s antics and didn’t rely on lots of references to remind you ofStewart’s glorious acting career.

Glenn Close
Glenn Close is no doubt one of the finest actresses to hit the silver screen whether she’s in a raunchy display inFatal Attractionor stealing puppies inDisneylive-action101 Dalmatians, she always gives a role her finest delivery. Her role as Homer’s mother Mona Simpson has definitelybrought out some of the best emotional momentsfrom her appearance in two specific episodes. Though she has reprised the roles in ten episodes, the episodesMother SimpsonandMona Leaves-ahave left lasting impressions onSimpsonsfans for years andbrought out a new side to Homer.
Not much is said of Homer’s mother in the six seasons prior, but in season seven it was time to reveal all how his hippie mother had been on the run for 30 years following the destruction of Burns' germs. Close provided a charming and emotional delivery as the doting mother who gave Homer a sense of closure and identity. Her departure at the end of the episodes creates a whole variety of emotions for Homer and for the fans where her departure once again hits home for many.Close’s soft voice and nurturing soulmade her the perfect voice for Mona who must be one of the least dislikedSimpsonscharacters.

Dustin Hoffman
Academy award-winning actor, Dustin Hoffman was one of the first celebrities to appear inThe Simpsonsin the episodeLisa’s Substitute.After filling in for the ill Miss. Hoover, Lisa grows a strong bond and admiration for him as an intelligent and emotional male role model in place of Homer. The episode features slight references to Hoffman’s previous work inThe Graduatein relation to a scene with Mrs. Krabappel who aims to seduce him. Hoffman’s delivery is one of a charismatic, educated, liberal, and positive influence on those around him and his feature is an important building block inHomer and Lisa’s relationship.
The beauty of this Hoffman episode is thathis lines create such emotionin nearly every scene he is in whether it’s readingCharlotte’s Web,making Homer a better dad, or saying goodbye to Lisa, a goodbye that has always been a poignant moment in the series. In an era whereThe Simpsonswriters could knock out emotional episodes like it was nothing, Hoffman’s delivery and overall lasting impact on Lisa make his departure from the series a resonating moment for characters and fans alike.

Michelle Pfeiffer
Homer has had a couple of love interests and connections in the early Simpsons seasons such as the belly dancer, and country singer Lurleen Lumpkin, but none had quite an impact as Mindy Simmons voiced by Michelle Pfeiffer. Afteran incredible performance as CatwomaninBatmanReturns,Pfeiffer would play a much more normal role as co-worker Mindy who was basically the female equivalent to Homer and his many characteristics and interests. Simmons is hired to meet discriminatory laws of having at least one woman working at the nuclear power plant. After Homer learns of her love for sleeping, eating, and genuinely being as lazy as can be, his infatuations and desires aim to get the better of him.
Though Lurleen wanted Homer, Mindy was the first real test of Homer’s commitment to Marge and is an interesting look at the internal challenges he goes through as to which life he would prefer. Pfeiffer delivers a solid performance like inmost of her movie rolesand her overall charm and lust for Homer make her one of the most intriguing characters the show has ever had. The episode is still debated by fans today about its conclusions on whether Homer ends up in bed with Mindy or Marge, though is disputed as most likely being Marge. Pfeiffer provided a warming voice to a character built for temptation and her one role in the show has certainly had a lasting impact as a fan favorite.

Danny DeVito
Herb Powell was definitely a character who fans wish theycould have more ofin the show and with a career playing avariety of eccentric characters, Herb Powell has to be one of DeVito’s most normal. Being the first character to open up Homer’s family tree and background, Herb is basically the polar opposite of Homer’s characteristics and successes, but there is no denying a similarity between the two of them. DeVito appeared in two episodes as Homer’s brother, firstly inOh Brother Where Art Thou?and then a season later inBrother Can You Spare 2 Dimes.The two episodes feel like a two-parter about the fall and rise of Herb’s character, both thanks to Homer in a sense.
DeVito’s rough New Jersey voice and anger at Homer relate tosome of his most iconic roles. Whetherhe’s shouting instructions at Herculesorcausing absolute chaos as Frank Reynolds, DeVito is an actor audiences love and his voice is so recognizable. Though Herb was not used again after season 3, it was featuring DeVito in those earlySimpsonsepisodes that brought a lot of celebrity attention to the show and really showed how much of a big dealThe Simpsonswas becoming. DeVito’s voice acting delivery is brilliant in these two episodes, as fans are treated to anger, joy, inquisitive, love, and sorrow. Herb has one of the best character developments of anySimpsonscharacter and it would be hard to imagine any other voice leaving the character’s lips other than DeVito.