Over the soon to be 28 season run of The Simpsonsthere have been many celebrity guest appearances. Usually when a celebrity makes a cameo, they are either playing a comedic version of themselves, or are voicing an entirely new character. Along with numerous actors and musicians, The Simpsons have even managed to get important political figures, like Tony Blair, on the show (he was the Prime Minister of Britain at the time of his recording).

Some of the most recent celebrity appearances haven’t exactly been up to snuff. The Lady Gaga episode, for example, was the lowest rated episode on IMDB at one point (a well deserved accolade). It seems that the poor quality of recent episodes is matched by the level of celebrities that have appeared, with people such as Cat Deeley, Jeff Ross, and Sammy Hagar having cameos in the last season.

We aren’t here today to talk about the ever-declining quality of the current episodes. Instead, we want to celebrate the good old days, and give props to the most memorable celebrity appearances from the classic era of The Simpsons. From the first Beatle to appear on the show, to the King of Pop himself, here are the 15 Best Celebrity Appearances On The Simpsons. 

15. Ringo Starr

Ringo Starr Simpsons 15 Best Celebrity Appearances On The Simpsons

The first season of The Simpsons is not fondly remembered by fans, due to the low quality of the animation and the individual characters of the Simpson family still being developed. It wasn’t until the second season that the show began to take form as one of the most beloved TV comedies of all time.

It took a few years for The Simpsons to earn enough acclaim and popularity to draw big stars. The biggest name actor on the show during the first season was Kelsey Grammer, who at the time was still only known as a cast member on Cheers (Frasier was still a few years away). This changed with the second season, as bigger names appeared on the show, such as Dustin Hoffman and Danny DeVito. One of the biggest celebrities to appear during this season was Ringo Starr.

In the episode “Brush With Greatness”, it is revealed that Marge used to paint pictures of Ringo Starr when she was in her teens. She sent him one of the portraits in her youth, and he is shown finally receiving it in the present day. Not only did Starr play himself, but he allowed the use of his song “It Don’t Come Easy” during a montage scene in the episode.

14. Tony Bennett

Tony Bennett Simpsons 15 Best Celebrity Appearances On The Simpsons

While the first season of The Simpsons did have a few celebrity voices, none of them appeared as themselves. This changed with the second season, and the first celebrity to appear as a Simpsonised version of themself was Tony Bennett. While other people appeared as themselves that season (like Ringo Starr), in terms of chronological episode broadcast order, Bennett was the very first.

Tony Bennett is a famous singer in the style of Frank Sinatra. He has recorded over 70 albums, and still tours regularly, despite being 90 years old. His appearance on The Simpsons was in the episode “Dancin’ Homer”, where Homer becomes the mascot of his local baseball team. Homer moves his family to Capital City (a New York-like big city). When the Simpson family arrive in Capital City, Tony Bennett is singing Capital City’s theme song. He even stops to say hello to Marge.

Not only did Tony Bennett appear as himself, he also recorded a song especially for this episode. “Capital City” was meant to be a parody of the song “New York, New York”. This song would later appear on the album Songs in the Key of Springfield, which consisted of tracks that appeared on the show (rather than original songs that the previous albums had).

13. Sting

Sting Simpsons 15 Best Celebrity Appearances On The Simpsons

Sting’s appearance in The Simpsons proved something important about the man – that he has a sense of humour.

During the third season episode “Radio Bart”, Bart hides an AM radio down a well, and uses a microphone to pretend that he is a boy trapped at the bottom. Bart puts on a voice and pretends to be a sweet, innocent kid named Timmy, who quickly wins over the hearts of the citizens of Springfield.

Krusty the Clown decides to gather a bunch of celebrities together in order to release a charity single. Sting is one of the musicians who joins the group, and together they recorded “We’re Sending Our Love Down the Well“. The whole segment of the episode is meant to satirise other famous charity songs, and Krusty even implies that most of the money won’t go to charity at all.

Sting’s inclusion in the charity single part of the episode shows that he doesn’t mind poking fun at himself. He was one of the big players behind what many consider to be the original charity song – “Do They Know It’s Christmas” (the 1984 version). According to Bob Geldof (one of the two men behind the song), Sting was the first person he called, and was the first to agree to perform. It seems his attitude towards the song had changed by the time 1992 rolled around, as he had no problem parodying the subject on The Simpsons. 

12. The Baseball Players From “Homer At The Bat”

The Simpsons Baseball 15 Best Celebrity Appearances On The Simpsons

Every other person on this list is either an actor or a musician (or Linda McCartney). It’s kind of expected of them to do a good performance in the role, and even the worst celebrity appearance on The Simpsons is usually well-voiced, if nothing else. What makes the cameos in “Homer at the Bat” special, is that they were all done by baseball players, with no prior acting experience. Despite not being performers, all of them did a great job, and their comedic performances knocked it out of the park.

The players who appeared in the episode were Wade Boggs, Jose Canseco, Roger Clemens, Ken Griffey, Jr., Don Mattingly, Steve Sax, Mike Scioscia, Ozzie Smith, and Darryl Strawberry. All of them were successful baseball players at the time, and had no prior acting experience. Each of them were given key scenes during the episode, and all of them pulled off their lines flawlessly.

“Homer At the Bat” is considered one of the best episodes of the show’s entire run, by both creators of the show and the fans. It was the first episode to beat The Cosby Show in the ratings (as they were competing for the same time slot on another network from The Simpsons). The episode is even credited with saving lives, as a poster showing the correct way of performing the Heimlich manoeuvre taught two people how to stop their friends from choking.

11. Michelle Pfieffer

Michelle Pfieffer Simpsons 15 Best Celebrity Appearances On The Simpsons

In the fifth season of The Simpsons, one of the most desirable women in the world brought her charms to Springfield. In “The Last Temptation of Homer”, Homer meets a beautiful women with a personality like his own. This was Mindy Simmons, a character voiced by actress Michelle Pfieffer. Throughout the episode, Homer is tempted to cheat on Marge by the woman of his dreams.

The episode is ranked among the classics, both for its humour and for the touching story of Homer resisting temptation and staying loyal to his loving wife. Michelle Pfieffer was, by all accounts, great to work with. She took the role seriously, and never considered voicing a cartoon to be beneath her (as she was one of the biggest actresses in the world at that time).

This spot on the list almost went to Beverly D’Angelo, for her appearance as Lurleen Lumpkin in “Colonel Homer”. The two episodes share a very similar premise (Homer is tempted to cheat on Marge by a more desirable woman, but remains loyal to her). The reason “The Last Temptation of Homer” is ranked as the better episode is due to the music in “Colonel Homer”; The Simpsons has had many original songs throughout the years, but they can be hit or miss. “Colonel Homer” had several musical numbers, whilst “The Last Temptation of Homer” was just funny gags.

10. Patrick Stewart

Patrick Stewart Simpsons 15 Best Celebrity Appearances On The Simpsons

Patrick Stewart is known for his two most iconic roles – Captain Jean-Luc Picard of the Enterprise from Star Trek: The Next Generation and Professor Charles Xavier from the X-Men movies. Although he will likely forever be associated with those roles, Stewart has had a long and illustrious career in acting that dates back to 1967.

In all of that time, Patrick Stewart has stated that he has one great regret over declining a role. He was asked to voice Jafar in Disney’s Aladdin, but he refused. It may have been the massive box office success of Aladdin that prompted him into taking a role on The Simpsons a few years later.

“Homer the Great” is considered one of the all time classic episodes. Homer joins The Stonecutters, a secret society similar to that of the Freemasons. It is revealed that Homer is the Chosen One, a man marked at birth who will lead The Stonecutters to greatness. Patrick Stewart voiced the character of Number One, the leader of The Stonecutters (whose name is a shout-out to one of Stewart’s catchphrases in Star Trek). Not only did he give a great performance, but he also was given the second part of the legendary “No Homer’s” joke.

9. Paul & Linda McCartney

PaulLinda McCartney Simpsons 15 Best Celebrity Appearances On The Simpsons

Ringo Starr was the first Beatle to show up on The Simpsons, and George Harrison would later gave a brief performance in “Homer’s Barbershop Quartet”. With John Lennon still being dead, that left only one Beatle to appear on the show – Paul McCartney.

In the seventh season episode, “Lisa the Vegetarian”, the writers on the show approached Paul McCartney and his wife Linda about doing a guest spot. Due to Paul being passionate about his vegetarianism, they felt that this episode would appeal to him. Paul agreed, but on one condition – if Lisa became a vegetarian in the episode, then she would have to stay as one for the remainder of the show’s run. The writers agreed,and have stayed true to their word – Lisa has remained a vegetarian for over twenty years now.

Along with appearing in the episode, Paul McCartney allowed the use of his song “Maybe I’m Amazed” over the credits. This version of the song also includes a reference to the popular “Paul Is Dead” myth. To those who are unaware, there is a long running urban legend stating that Paul McCartney died at some point, and was replaced by a look-a-like so as not to break up The Beatles. If the version of “Maybe I’m Amazed” from the episode is played backwards, Paul can be heard reciting a lentil recipe (which is a reference to a joke in the episode), followed by “Oh, and by the way, I’m alive“.

8. Adam West

Adam West Simpsons 15 Best Celebrity Appearances On The Simpsons

Just because a celebrity appearance is short, doesn’t mean it can’t be memorable.

In the 4th season episode “Mr. Plow”, Homer is looking to purchase a new car after destroying his old one in a crash. Whilst attending a local car show, Homer & the kids run into Adam West, who is there with the original Batmobile. After reminiscing about his days playing Batman, and criticising the “new” portrayals of Batman and Catwoman (a joke that doesn’t work as well nowadays, due to many other Batman films released in the meantime), Adam West scares off the family with his dancing.

The only regrettable part of Adam West’s appearance is that it has since been ruined (like a great many other things) by Family Guy. For over fifteen years now, Adam West has played a wackier version of himself as the mayor of Quahog in Family Guy. While he was one of the best parts of the show, the joke has long since been run into the ground (like most of Family Guy’s jokes.)

7. Glenn Close

Mona Simpson Simpsons 15 Best Celebrity Appearances On The Simpsons

Grampa is one of the oldest characters on The Simpsons, in both his physical age and how long he has been on the show. He is one of the few characters outside of the immediate family who has existed since the era of the Tracy Ullman Show shorts (along with Krusty, Itchy & Scratchy and the Happy Little Elves). While Grampa has existed for a long time, no mention of the fate of Homer’s mother was made until the seventh season episode, “Mother Simpson”.

Homer’s mother was revealed to be Mona Simpson, who was forced to run away when Homer was a boy, due to being identified as one of the people who destroyed Mr. Burns’ Germ Warfare laboratory. She was voiced by actress Glenn Close, who would go on to reappear as Mona Simpsons in five later episodes.

“Mother Simpson” is regarded as one of the best episodes in the series, especially by the creators of the show, many of whom have lauded it for its mixture of humour and emotion. The final scene of Homer staring at the stars has been stated by Bill Oakley (the showrunner during the period when this episode was first broadcast) as the one part that makes him get “teary-eyed”.

6. Dustin Hoffman

Dustin Hoffman Simpsons 15 Best Celebrity Appearances On The Simpsons

Dustin Hoffman was one of the first big celebrities to appear on the show. In the second season episode “Lisa’s Substitute”, Hoffman played a substitute teacher in Lisa’s class named Mr. Bergstrom, whom she has a crush on. Due to Mr. Bergstrom’s intelligence and teaching skills, Lisa begins to see him as a better role model than her own father.

What helps cement Dustin Hoffman’s excellent performance in the minds of the fans is his final scene with Lisa. The note that he gives her that says “You are Lisa Simpson” is one of the most touching and memorable scenes in the show’s history.

One peculiar thing about “Lisa’s Substitute” is that Dustin Hoffman’s name does not appear on the credits. This was an intentional move on Hoffman’s part, as the divide between TV actor and movie actor was still a prevalent thing at the time. Due to Dustin Hoffman still mainly appearing in films at that time, he asked to use a pseudonym in the credits (which was pointless, as news of his involvement leaked almost immediately). He is credited as Sam Etic, a play on the word Semitic, which refers to both Hoffman’s and Mr. Bergstrom’s Jewish heritage.

5. Kelsey Grammer

Sideshow Bob Simpsons 15 Best Celebrity Appearances On The Simpsons

Kelsey Grammer is one of the longest running guest cast members of The Simpsons. His first appearance as the diabolical Sideshow Bob happened during the show’s first season. At that point in time, Kelsey Grammer was the biggest celebrity to appear on the show, due to his portrayal of Dr. Frasier Crane on Cheers. Sideshow Bob has made nineteen appearances since 1990.

As one of the few long running characters on the show, Sideshow Bob has several classic episodes under his belt. To choose between episodes like “Cape Feare”, “Sideshow Bob’s Last Gleaming”, and “Brother From Another Series” would be a disservice to their quality. Kelsey Grammer has given consistently incredible performances as Bart’s deranged enemy, and much like the character he portrays, manages to excellently mix high-brow class with slapstick humour.

With all of this acclaim and influence on the show’s history, why isn’t Sideshow Bob at the top of the list? Much like the show itself, Bob’s appearances have worn out their welcome. In recent years, there have been many bad Sideshow Bob episodes (which is no fault of Kelsey Grammer’s, he still gives excellent performances, its just the writing that is bad). The new episodes aside, Sideshow Bob has made so many classic appearances that he deserves a high spot on this list regardless.

4. James Woods

James Woods Simpsons 15 Best Celebrity Appearances On The Simpsons

In the fifth season episode “Homer and Apu”, Homer gets Apu fired from the Kwik-E-Mart after helping expose the fact that Apu was selling expired goods. During his absence, Apu is replaced by actor James Woods, who takes the job in order to research for a movie role.

“Homer and Apu” is often regarded as one of the best episodes of the shows run. A large part of this is due to James Woods’ performance, and willingness to make fun of himself. Most of his jokes are about the lengths an actor will go to for method acting, and his own neurosis about his abilities.

Much like the Adam West entry on this list, the idea of James Woods playing a wackier version of himself was also ran into the ground by Family Guy. Whereas The Simpsons version of James Woods was more about the extremes he is willing to go in order to prepare for a role, Family Guy portrays him as an evil stalker, who is obsessed with Peter Griffin. Like all things with Family Guy, the joke was overused to the point of boredom.

3. Leonard Nimoy

Leonard Nimoy Simpsons1 15 Best Celebrity Appearances On The Simpsons

In “Marge vs. the Monorail”, a scam artists convinces the citizens of Springfield to vote for the creation of a Monorail. During the star-studded opening for the Monorail, Star Trek‘s Leonard Nimoy acts the Grand Marshall of the event. Throughout the episode, Nimoy is portrayed as annoying people with his reminiscing about Star Trek (which is ironic, as his first autobiography was called I Am Not Spock).

Leonard Nimoy wasn’t the first choice of celebrity to appear in this episode. Fellow Star Trek alumni George Takei was originally approached to star in the Monorail episode. He had to refuse, however, as he was a member of the Southern California Rapid Transit District, and he thought the episode would make public transport look bad.

In the eighth season episode “The Springfield Files” Leonard Nimoy appeared for a second time. This episode was meant to be a satire of the hugely popular show The X-Files, and featured cameos from its two leads, David Duchovny and Gillian Anderson. Nimoy showed up as part of the framing device of the episode, where he introduced the story (as a parody of another show he worked on called In Search Of…), and he would appear again during the episode’s final song and dance number.

2. Danny DeVito

Herb Powell Simpsons 15 Best Celebrity Appearances On The Simpsons

Danny DeVito is one of the few celebrities to appear in several different episodes of the show. He played Herb Powell, Homer’s wealthy half-brother.

Herb’s first appearance was in the episode “Oh Brother, Where Art Thou?”, where Homer discovers he has a half-brother that he has never met before. This brother turns out to be Herb Powell, the wealthy owner of a car manufacturer. Herb grows to love Homer and his family, and even entrusts his brother with the task of designing a new car for the company. Homer’s car turns out to be a “monstrosity“, that ends up bankrupting Herb and his company. The episode ends on a sour note, as Herb tells Homer that he “has no brother”.

The relationship between Homer and his brother would be saved in a later episode. In the third season episode “Brother, Can You Spare Two Dimes?”, Herb reappeared, this time in a starring role. After becoming destitute following his creation of Homer’s car, Herb has a new idea for a product that will make him rich. Homer, meanwhile, earns a $2000 bonus from Mr. Burns, following a report showing that his sperm count had been lowered from working in the Nuclear Power Plant. Homer gives Herb the money, which allows him to create a device that translates the noise a baby makes into English.

There is a good reason that Danny DeVito was one of the rare actors who was asked to return for more appearances, his performance as Herb is one of the best in the show’s history (helped by DeVito being a legitimate comedy actor). While the first episode ended on a downer, Herb’s second appearance where he makes forgives Homer and the two make amends makes for one of the most compelling stories in The Simpsons history.

1. Michael Jackson

Michael Jackson Simpsons 15 Best Celebrity Appearances On The Simpsons

While there had already been several celebrity appearances on The Simpsons by 1991, the upcoming third season was rumoured to feature the voice of the biggest star on the planet. It was eventually confirmed that the King of Pop himself, Michael Jackson, was going to voice a character in the season premiere.

“Stark Raving Dad” was the first episode of the third season of The Simpsons. Homer is accidentally sent to a mental institution, where he encounters Leon Komposkwy, a man who believes himself to be Michael Jackson. The episode is perhaps best known for the final musical number, where Bart and Leon perform the song “Happy Birthday Lisa” (as her Birthday had been forgotten earlier in the episode). Contrary to popular belief, whilst Michael Jackson wrote the song, he was unable to perform it due to contractual obligations. The song was actually performed by Kipp Lennon, a singer who worked on many Simpsons episodes. The track would later appear on Songs in the Key of Springfield, but Jackson had to use an assumed name as writer of the song (he was called W.A. Motzart.)

Michael Jackson’s involvement with The Simpsons was not just limited to the cartoon. In 1990, the first of many Simpsons music albums was released. The Simpsons Sing the Blues consisted of mostly original songs performed by the cast of the show. One song on the album named “Do the Bartman” went on to become a huge smash hit across the world, hitting the number one spot in many countries. This song was co-written, co-produced and featured backing vocals from Michael Jackson, who had to keep his involvement in the song a secret for a long time due to his other contractual obligations.

Honourable Mention. Tom Hanks

The Simpsons Movie 15 Best Celebrity Appearances On The Simpsons

While The Simpsons Movie was more forgettable than bad, it did have a few laugh out loud moments. The film was essentially several different episodes worth of plots that were thrown haphazardly together (seriously, what was the point of the Irish boy that Lisa falls for?). It was an average film at best, and wasn’t worth waiting almost twenty years for.

One thing that The Simpsons Movie was lacking in was star power. The band Green Day show up for a few minutes at the beginning of the movie, Albert Brooks plays the voice of Hank Scorpio in a lamer character’s body, and Arnold Schwarzenegger was in the film, but was voiced by Harry Shearer. The rest of the cast were just the regulars of The Simpsons TV show… with one big exception.

Tom Hanks appears in the movie, and gives a brief, but memorable appearance as himself during a commercial for the “New Grand Canyon” (a cover-up for the plan to destroy Springfield). For giving the movie one of its best moments, Mr. Hanks deserves an honorary spot on this list.

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