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The Simpsons Best One-Time Guest Stars

So many to choose from...

By Fergus JeffsPublished 3 years ago 28 min read
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(c) Wikimedia Commons Author: Rastrojo

In nearly 700 episodes, The Simpsons have utilised the voice talents of hundreds of celebrity guests. From the briefest of walk-on cameos to becoming the focus of an entire episode, guest stars have become part of the show's lifeblood for better and worse. People have performed as an entirely original character, just as themselves or even as a fictionalised version of themselves as created by The Simpsons writing team. Certain voice actors have proved successful and have been invited back for further appearance(s).

However, this Simpsons post will focus on one-time guest appearances. The best one-time guest stars in the history of The Simpsons. The people who appeared on one episode and never returned to the show. This means that you will not see regular guest voices like Phil Hartman, Kelsey Grammar, Albert Brooks or Jon Lovitz in the following list. The following list is not ranked; it selects 20 Simpsons guest stars that I believe significantly impacted the show's history.

Dustin Hoffman- Mr Bergstrom- Lisa's Substitute

I am beginning with an obvious one here. Dustin Hoffman is not the first one-time guest star in Simpsons history; he is undoubtedly one of the first to significantly impact its history. In the episode 'Lisa's Substitute' (Season 2, Episode 19), Hoffman plays Mr Bergstrom, Lisa Simpson's substitute teacher. After Lisa's regular teacher Miss Hoover is ill, Mr Bergstrom steps in a short-term replacement for her 2nd-grade class. Mr Bergstrom's unorthodox teaching methods inspire Lisa, presenting her with the positive male role model that she may not be getting at home.

Dustin Hoffman would lend his voice to 'Lisa's Substitute' with the request that he be credited under the name 'Sam Etic' on the episode's closing credits. As The Simpsons was still early in its run, Hoffman was unsure about being associated with an animated show. However, he would not hold back in his performance as Mr Bergstrom. Mr Bergstrom is the substitute teacher that we all wished for during our schooldays. Hoffman imbues him with kindness, a love for learning and a unique way of challenging his students. All of Miss Hoover's class seems to benefit from Mr Bergstrom's teaching, with the often creatively stifled Lisa being given a chance to blossom. People at the time may not have known that Sam Etic was a pseudonym. However, obtaining the services of one of Hollywood's elite actors was a huge 'get' for The Simpsons in just their 32nd production episode.

Finally, Hoffman is involved in one of the show's most famous moments. Bidding Lisa and emotional farewell at Springfield's train station, he writes her a note that she can read every time she feels alone. On the letter is written, 'You are Lisa Simpson.' A heartfelt moment from the show's early years that still tugs at the heartstrings to this day that is made better by Dustin Hoffman.

Meryl Streep-Jessica Lovejoy-Bart's Girlfriend

This entry moves from one of Hollywood's finest actors to the most nominated actor in film history. A recipient of three Oscars, two BAFTAs, nine Golden Globes and three Primetime Emmy Awards, Meryl Streep would guest star on The Simpsons during the show's sixth season. Appearing in the episode's 'Bart's Girlfriend', Streep would play Jessica Lovejoy, Reverend Lovejoy’s daughter. Bart quickly develops an attraction for Jessica, subsequently trying to be a good kid to impress her. However, beneath her 'reverend's daughter' façade, Jessica is more badly behaved than Bart, actively encouraging Bart's troublemaking side as their relationship continues. Bart knows that the relationship is wrong, but Jessica can make Bart do whatever she wants.

It took me a long time to realise that Meryl Streep voiced Jessica Lovejoy, only finding out after reading The Simpsons: A Complete Guide to Our Favourite Family. Streep's voice is pitched high enough that she is entirely convincing playing a 10-year-old girl. During the episode's production, Nancy Cartwright and Meryl Streep recorded all their lines together. You can tell by how well the two play of one another. Streep portrays Jessica as someone who is eviler than Bart is. Despite being perceived as the minister's daughter, Jessica thrives on mischief. She first pays Bart any real attention after his 'Scotchtoberfest' prank goes awry and is only interested in his 'bad boy' nature. Streep plays Jessica in a way where she continually looks down on Bart throughout the episode (be he good or bad), but in a way that he cannot get her out of his mind. She beguiles Bart, dragging him into misbehaviour or successfully managing to pin the blame on him for something he didn't do.

Who would have thought that one of Hollywood's most awarded actors would make for an excellent Simpsons guest star?

Kathleen Turner- Stacy Lovell-Lisa vs Malibu Stacy

In the Season 5 episode 'Lisa vs Malibu Stacy', Lisa is disappointed to find that a talking Malibu Stacy doll spouts sexist phrases. To get the brand's attention, Lisa teams up with the doll's original creator Stacy Lovell to create the more empowering and aspirational talking doll Lisa Lionheart.

In this episode, Lovell is portrayed by Kathleen Turner (in her first TV role). Tuner excellently performs Stacy Lovell as a bitter and jaded creator. When Lisa first meets Lovell, she has become a recluse, forced out of her own company after being told that her ideas were not 'cost-effective'. With Yeardley Smith playing Lisa at her morally crusading best, Turner works both against and in tandem with Lisa in her role as Stacy. When Lisa first asks for Stacy's help, Turner says the line "Not now, I'm...too drunk" and sighs in such a way that you can understand why Lisa responds by leaving the room in frustration. Once she has agreed to create Lisa's doll, Lovell is determined that Lisa Lionheart is a success, and Turner conveys these feelings.

For her television debut, Kathleen Turner definitely began with a brilliant performance.

James Woods-Himself-Homer & Apu

In The Simpsons fifth season, the show's writing team decide to give Apu his own spotlight episode. In the episode 'Homer and Apu', Homer contracts food poisoning from an expired sausage he bought at the Kwik-e-Mart. Participating in a hidden-camera news investigation, Homer manages to expose Apu's unsanitary food policies, resulting in the latter being fired from his job. As an apology, Homer lets Apu stay with the Simpson family and helps him get his job back. Meanwhile, actor James Woods is hired as Apu's replacement at the Kwik-E-Mart, the actor taking the role as research for his next movie role.

One of the few guest stars who truly steals every scene he is in; James Woods deserves to be considered one of The Simpsons greatest guest stars. When the show did not regularly feature celebrities playing themselves, he delivers such humour and energy to every line he is given. One particular exchange in the Kwik-E-Mart between Woods and Jimbo serves as the episode's standout moments. Even a scene of James Woods scraping cheese from inside a microwave while talking to his agent is excellent. He is even starstruck when he meets Apu, saying, "You were like the guy around here", and claiming that he has seen all of his security tapes.

He was so successful in his guest appearance that Family Guy decided to make him a recurring guest character over a decade later. That fact alone makes for one of the best moments of the Simpsons/Family Guy crossover episode 'The Simpsons Guy' where the two show's versions of James Woods appear on-screen next to one another.

John Waters-John-Homer's Phobia

A couple of examples on this list see notable people guest star on The Simpsons as characters that share distinguishing features or personality traits with their real-life self. The first example of this trope is the director and John Waters appearing as the character 'John' in the Season 8 episode 'Homer's Phobia'. The character of John is the owner of a collectables shop in the Springfield Mall. However, he still shares the hairstyle and distinctive pencil-thin moustache of the real John Waters.

In 'Homer's Phobia', the Simpson family make a new friend in John. Homer and John get on particularly well. However, when Homer finds out that John is gay, he shuns the man while the rest of the family continue to spend time with him. When Homer sees Bart wearing a women's wig and a Hawaiian shirt, he fears that Bart might be turned gay by John and sets out to ensure Bart's heterosexuality.

At the time, a controversial episode topic, 'Homer’s Phobia’, would receive critical praise for its discussion of the issue and from the LGBT community for its anti-homophobic message. The episode would receive a Primetime Emmy for Outstanding Animated Programme and an award from GLAAD Media for ‘Outstanding TV-Individual Episode’. Some of the praise that ‘Homer’s Phobia’ has to go the performance of John Waters. From the minute he comes on screen, Waters makes the role of John an incredibly likeable one. Even when Homer is acting irrationally towards him, John still treats him well. Still, he questions Homer on why he holds his particular views on homosexuality. Even at the end of the episode, John comes to Homer’s rescue and later earns his respect.

As thanks for his performance, The Simpsons writers gave John Waters an animation cel from this episode. Waters still has the cel hanging in his office to this very day.

Adam West-Himself-Mr Plow

Adam West is another one-time Simpsons guest who would later have a recurring role on Family Guy. West is not given the same amount of screen time as James Woods in the episode that he appears in but maximises his minutes in the performance he delivers. West appears in the classic Season 4 episode ‘Mr Plow’, where Homer starts his own slow-plowing business under the name ‘Mr Plow’. After initial success, Homer soon faces competition from Barney, who starts operating his snow-plowing business under the name ‘The Plow King’. Even though singer Linda Ronstadt is featured more in the episode, Adam West’s scenes are remembered more by The Simpsons fanbase.

In the episode’s first act, Adam West first appears at a car show visited by the Simpson family. With Homer introducing West to Bart and Lisa as ‘Batman’, the two do not recognise West. In an iconic moment, West then asks why Batman doesn’t dance anymore and then begins to, causing Bart, Lisa and Homer to back away, unsettled by this encounter. Later in the episode, Homer meets West again when expecting to plow his driveway. However, Barney got there first. The way that Adam West delivers the line “There was (a job) when I called you, 45 minutes ago” is delivered in such an intense way that you cannot help but laugh. Despite appearing in just two scenes during the episode, West’s performance is one reason why ‘Mr Plow’ is regarded as one of The Simpsons best episodes.

Rodney Dangerfield-Larry Burns-Burns Baby Burns

The other example on this list of actors portraying a character close to their own personality is Rodney Dangerfield’s guest appearance in another Season 8 episode, ‘Burns Baby Burns’. The episode sees the legendary comedian play Larry Burns, the long-lost son of Mr Burns. After finding out his location and hitching a ride with the Simpson family, Larry meets his father for the first time. At first, Mr Burns tries to find Larry's place in high society but soon finds that Larry is nothing like him. When Mr Burns disowns his son, Larry and Homer hatch a plan to get Burns to admit that he loves his son, a plan filled with hilarious moments.

As a fan of his scene-stealing performance in the 1980 comedy film Caddyshack, it is a pleasure to see Rodney Dangerfield on top form as Larry Burns in this episode. Dangerfield delivers every line in his own recognisable style. Lines like “Put her back in, she ain’t done yet” are done with such oafish charm that it never fails to get a laugh even on repeated viewings. Larry and Homer seem like two people who would find a lot in common with one another. The performances of Rodney Dangerfield and Dan Castellaneta prove this to be true.

Even though Rodney Dangerfield is pretty much playing himself when portraying Larry Burns, he still deserves his place as an excellent Simpsons guest star.

Harvey Fierstein-Karl-Simpson and Delilah

Harvey Fierstein is another name that should be included on any list of the best Simpsons guest stars. Fierstein would appear as the character Karl in the Season 2 episode ‘Simpson and Delilah’. In ‘Simpson and Delilah’, a formula gives Homer a full head of hair. Also obtaining a new assistant named Karl, Homer manages to climb the corporate ladder at the Springfield Nuclear Power Plant, much to Waylon Smithers' chagrin.

Harvey Fierstein's performance in ‘Simpson and Delilah’ meant that The Simpsons sophomore season began in ideal fashion, continuing on from the excellent season opener ‘Bart Gets an F’. Even though he only provides Karl’s voice, Fierstein commands the scene whenever he opens his mouth. The famously raspy voice is forceful and decisive, giving Homer confidence and driving him forward in his career. Even when Homer loses his hair tonic, Karl gives him the belief to give an important speech to the power plant shareholders.

The impact of Harvey Fierstein’s performance can be seen in how Karl is animated. Smooth and passionate, tender but forceful towards, Karl gives Homer the most success he has ever experienced working for Mr Burns. Even when Homer and Karl eventually part ways, their last moments together are emotional. After being fired by Mr Burns, Karl offers his umbrella to the now-bald Homer when he leaves, preferring to walk in the rain then see his former boss get soaked.

Thanks to Harvey Fierstein's performance, ‘Simpson and Delilah’ goes from being just another early Simpsons episode to a must-watch in the pre-golden era days of the show.

Jose Canseco, Don Mattingly, Ozzie Smith, Darryl Strawberry, Steve Sax, Roger Clemens, Ken Griffey Jr, Wade Boggs-Themselves-Homer At The Bat

The Season 3 episode ‘Homer at the Bat’ is often regarded as one of the best episodes in The Simpsons history. The episode saw The Simpsons defeat The Cosby Show in the ratings for the first time. It is also one of the funniest episodes in the show’s history. It is also miraculous that ‘Homer At The Bat’ could turn out as great as it is, considering that it guest-starred nine Major League Baseball players.

The plot of ‘Homer at the Bat’ sees Homer become the star batter for the Springfield Power Plant company softball team. However, Mr Burns bets rival Shelbyville Power Plant over the winner of the match between the two sides. To ensure that Springfield Power Plant is victorious, Mr Burns drafts in Jose Canseco, Don Mattingly, Ozzie Smith, Darryl Strawberry, Mike Scioscia, Steve Sax, Roger Clemens, Ken Griffey Jr and Wade Boggs as ‘ringers’ for his team ahead of the regular workers. However, a series of hilarious but unfortunate circumstances soon occur to stop the professional players from making it to the championship game.

It is always a risk when casting non-actors in a sitcom, as you do not know how well they will do when put in an unfamiliar situation. Sportsmen are always presented as rather serious individuals, so asking nine professional baseball players to engage in wacky animated sitcom scenarios. Therefore, the fact that the Major League players were game enough to engage in said scenarios is brilliant. Ken Griffey Jr, Wade Boggs and Don Mattingly get the best sub-plots out of the bunch and perform their roles as well as they possibly can. Overall, the players do not look out of place in this episode. Compared to modern-day episodes, where sportspeople are often brought in to record a random cameo, the nine ‘ringers’ are brought in to be sportsmen. This is one of many strengths that make ‘Homer At The Bat’ a series classic.

Johnny Carson, Hugh Hefner, Bette Midler, Luke Perry, Elizabeth Taylor, Red Hot Chilli Peppers-Themselves-Krusty Gets Kancelled

In a plot focused on Krusty the Clown, the Season 4 finale ‘Krusty Gets Kancelled’ delves into the entertainment world to find a host of famous guest stars. The emergence of a rival kids’ TV show hosted by the puppet Gabbo sees Krusty’s viewership wane to such an extent that his programme is taken off the air. Following this cancellation, Bart and Lisa enlist a host of celebrities to help the bedraggled clown stage a live comeback special.

In a similar fashion to the previous entry, ‘Krusty Gets Kancelled’ involves putting a series of celebrity guests in zany sub-plots. Compared to ‘Homer At The Bat’, the celebrity guests featured in ‘Krusty Gets Kancelled’ are more experienced in appearing on television shows. However, the potential risk here is whether these big-name celebrities would be willing enough to appear on a show like The Simpsons. The number of big-name celebrities could also slow down the episode's pacing, as the show tries to incorporate each of these stars onto the screen.

However, like ‘Homer at the Bat’, ‘Krusty Gets Kancelled’ manages to serve as a rather special season finale. Each of the guest stars is given their own killer line or set-piece throughout the episode. From Krusty suggesting alternate lyrics to the Red Hot Chilli Peppers to strongman Johnny Carson to eco-warrior Bette Midler, everybody gets their chance to shine. However, Luke Perry serves as the clear MVP of this episode. Luke Perry being Krusty’s half-brother, is alone the funniest joke in the episode. The relationship between the two family members is rightfully mined for laughs. Like the previous entry, ‘Krusty Gets Kancelled’ is an example of how to handle and treat a series of guest stars within a 22-minute animated programme.

Michelle Pfeiffer-Mindy Simmonds-The Last Temptation of Homer

In 1992, Michelle Pfeiffer would appear as Selina Kyle/Catwoman in Batman Returns. She would deliver an iconic performance that is still fondly remembered by Batman and comic book movie fans nearly thirty years later. Just over one year later, Pfeiffer would appear in another iconic role, playing Homer Simpson’s female equivalent in The Simpsons fifth season. Appearing in ‘The Last Temptation of Homer’, she plays Mindy Simmonds, Homer’s new co-worker at the Springfield Power Plant. To Homer’s dismay, Mindy is an attractive woman who shares his love of food (especially doughnuts) and taking naps at work. Despite Homer’s reluctance, the world seems to be pushing him towards a romantic relationship with Mindy, and Homer finds himself ever-so-slightly tempted by the offer.

Following Season 1’s ‘Life in the Fast Lane and Season 3’s ‘Colonel Homer, ‘The Last Temptation Of Homer’ would become the third Simpsons episode dealing with someone catching the eye of either Homer or Marge. However, unlike Jacques or Lurleen Lumpkin, Mindy Simmonds is not as open with her attraction towards Homer. Michelle Pfeiffer does an excellent job as Mindy. Being asked to do her own version of Homer Simpson drooling over some food, she achieves this feat. Pfeiffer is utterly believable as a female version of Homer. A highlight for me is when she excitedly says to Homer, “Let’s call room service,” while rapidly picking up the phone at the same time.

Michelle Pfeiffer and Dan Castellaneta's performances make for such excellent chemistry between Homer and Mindy that any resulting relationship between the two characters would be a convincing one. Despite each party’s attraction to one another, you can sense the discomfort between the two of them as they are seemingly pushed together at every available opportunity.

For someone who had never done voice acting before appearing on the show, Michelle Pfeiffer’s acting talent truly comes through in ‘The Last Temptation of Homer's climax. When Homer seems resigned to the prospect of himself and Mindy sleeping together, she tells him that he knows how she feels about him, but they do not need to do that Homer doesn’t want to do. When Pfeiffer says these lines, it sounds like she is talking to an actual person rather than an animated character. Michelle Pfeiffer’s performance in this Simpsons episode should not be slept upon.

Sara Gilbert-Laura Powers-New Kid On The Block

The second example on this list of a guest voicing Bart Simpson’s love interest, Sara Gilbert’s performance would proceed Meryl Streep’s by two series. In Season 4’s ‘New Kid On The Block’, the Simpsons receive new neighbours in Ruth Powers and her daughter Laura. Bart and Laura immediately become friends, with the Simpson boy even developing a crush on her. When Laura babysits Bart and Lisa, Bart tries to impress her. However, she breaks his heart when announcing that she is dating school bully Jimbo Jones. Now, Bart attempts drastic measures to split up the happy couple.

When she appeared on the show, Sara Gilbert was known for playing Darlene Conner, the tomboy, teenage middle daughter on Roseanne. She plays a similar role as Laura Powers, and she certainly plays the part well. Despite being a couple of years older, the character of Laura works perfectly with Bart. She knows all the same tricks that he does and relates to him quite well. She simultaneously works as his crush, friend, mentor and accomplice, all rolled into one person.

Sara Gilbert plays her as fairly easy-going, someone who could get on with just about anybody. She plays Laura as a very cool character, complete with an army jacket. She makes Laura Powers the babysitter that anyone would have wished for growing up. Such is the quality of Gilbert’s performance that you really feel for Bart when he gets his heart figuratively broken. The way that she says, “You won’t be needing this”, before pulling the beating heart right out of his chest and throwing it into the bin, makes you reach for your own to check that it is still there.

Pamela Reed (the voice of Ruth Powers in this episode) would return for further guest appearances following ‘New Kid On The Block’. The same could not be said for Sara Gilbert. I know that her story with Bart is wrapped up within the confines of her single episode, but it would have been great to see the return of Laura Powers further down the line. However, the character of Laura Powers and the voice performance of Sara Gilbert makes ‘New Kid On The Block' an episode well worth revisiting.

Lawrence Tierney-Don Brodka-Marge Be Not Proud

Lawrence Tierney was an actor known for a particular type of role on screen. Throughout his 57-year acting career, Tierney would be known for playing tough guys, including the leading role in 1945’s Dillinger and 1947’s Born To Kill. These parts would continue throughout his career, even up to his role as mob boss Joe Cabot in 1992’s Reservoir Dogs.

However, for people of a certain age, Lawrence Tierney will be known for his performance as security guard Don Brodka in The Simpsons Season 7 episode ‘Marge Be Not Proud’. The episode sees Bart attempt to shoplift the video game Bonestorm before being caught by Don Brodka. When Marge finds out about Bart’s crime, she emotionally distances herself from him, leading to Bart’s working to win back his mother’s love.

Speaking all his lines in a Southern growl, Don Brodka only appears in the first act of ‘Marge Be Not Proud’, but his influence looms large over the rest of the episode. To Don Brodka, Tierney brings the intimidating nature that he brought to many of his film characters (and even his real-life persona). When you watch ‘Marge Be Not Proud’, you find yourself worrying for Bart once Brodka has caught him shoplifting. When Bart unwillingly returns to the store with the rest of the family, you can sense the looming dread that at any moment Brodka could catch him.

As well as bringing a sense of intimidation and fear to the character, Lawrence Tierney delivers certain lines in such a deadpan manner that you cannot help but laugh out loud. A particular moment comes when Brodka breaks a plastic knife while trying to eat his pack of ‘Lunchables’. The reaction given by Tierney is nothing short of hilarious. Despite what happens in the rest of the episode, Tierney’s performance is excellent enough that you leave the episode still thinking about Don Brodka.

Although he may not be the most famous guest star the show would call upon during their golden years, Lawrence Tierney’s Simpsons role lives long in the memory.

Donald Sutherland-Hollis Hurlbut-Lisa The Iconoclast

Donald Sutherland might not be one of the first names that come to fans’ minds when they think of great Simpsons guests. However, I would argue that he deserves his place on this list and even go as far as to say that his vocal performance is underrated. Donald Sutherland was the primary guest in Season 7’s ‘Lisa The Iconoclast’. When researching a school essay for Springfield’s bicentennial, Lisa discovers a shocking truth about town founder Jebediah Springfield. However, she risks angering the townsfolk if she chooses to reveal this new information. Donald Sutherland plays Hollis Hurlbut, the curator of the Springfield Historical Society, who Lisa turns to when researching her essay. He shows hostility towards her when she presents her findings to him. It later transpires that Mr Hurlbut knows more about Jebediah Springfield than he is willing to admit.

Donald Sutherland is ideally suited for this role. He works as an intellectual curator who has decided to keep certain parts of history hidden. We get to see different sides of Hollis Hurlbut during his only appearance on The Simpsons. At first, we see the intelligent and personable historical expert with who Lisa befriends and bonds through their shared passion for history. We see his sceptical side when Lisa presents her research to him and the bicentennial committee. We see his devious side in a flashback when he steals Jebediah Springfield’s silver tongue when no one is looking. Finally, we see his defensive side when Lisa questions him about the truth, and he eventually crumbles. Donald Sutherland showcases all these sides, creating a multi-faceted character in the space of one episode.

Donald Sutherland is an underrated Simpsons guest from an underrated Simpsons episode.

Kirk Douglas-Chester J. Lampwick-The Day The Violence Died

Throughout the show’s early years, The Simpsons writers loved writing episodes about everyone’s favourite animated cat and mouse duo, Itchy and Scratchy. Seasons One to Eight had produced ‘Itchy and Scratchy and Marge’ (Season 2), ‘Itchy and Scratchy: The Movie’ (Season 4), ‘The Front’ (Season 4), ‘Itchy and Scratchy Land’ (Season 6), and ‘The Itchy and Scratchy and Poochie Show’ (Season 8). ‘The Day The Violence Died’. Season 7’s Itchy and Scratchy-centric episode would see The Simpsons production team call upon a star from Hollywood’s ‘Golden Age’. The plot of ‘The Day The Violence Died’ involves Bart meeting a homeless man named Chester J. Lampwick, who claims to be the original creator of Itchy and Scratchy. Despite a lack of evidence, Bart helps Chester sue Roger Meyers Jr. and Itchy & Scratchy Studios for $800 million. For the role of an elderly homeless man and animation pioneer, the producers would cast Spartacus himself, Kirk Douglas.

Douglas was not the writer’s first choice for Chester J. Lampwick (they originally wanted William Hickey), but the 79-year-old would prove to be a more than adequate replacement. Douglas’s voice, changed by age, worked perfectly for Chester, an embittered pioneer who feels like he was screwed out of what he created and now seeks to get his just dues. All that Chester wants is to be recognised as the creator of Itchy and Scratchy. Once he has achieved this goal, he doesn’t care one jot about bringing the characters back when Bart and Lisa ask him for seed money. Douglas really sells Chester’s grumpy demeanour, a demeanour that changes as his relationship with Bart continues. His petty quarrels with Grampa and Krusty are hilarious, and the sound of Kirk Douglas licking his lips for liver and onions proves the man’s status as a legend.

Johnny Cash-Space Coyote-The Mysterious Voyage of Homer

‘El Viaje Misterioso de Nuestro Jomer’, translated as ‘The Mysterious Voyage of Homer’, is perhaps one of the strangest episodes in The Simpsons history. At the annual chilli cook-off, Homer eats two Guatemalan insanity peppers. The peppers cause Homer to hallucinate, sending him on a spiritual and psychedelic trip, where a talking coyote helps Homer find his soulmate. The job of voicing Homer’s coyote spirit guide went to legendary country singer Johnny Cash in what would be the final role of his acting career. In an episode filled with psychedelic imagery, Johnny Cash's voice emanating from a red coyote is somehow not the weirdest thing about this episode.

The Man In Black's iconic deep voice gives the Space Coyote an immediate presence after his face first appears in the sky above Homer. Like Don Brodka, the coyote’s time on-screen might be brief, but the creature's effect on Homer sets up the rest of the episode’s plot. The booming timbre of Cash’s voice makes Homer and the audience want to pay attention to what advice the coyote is communicating. Even if he cannot stop himself from gnawing on Homer’s trouser leg.

As with most of the guest stars on this list, Johnny Cash gets some humorous moments. When Homer is actively searching for his soulmate, he hears the voice of the spirit guide reminding him to find that soulmate. When Homer asks for more information, the coyote says that he cannot reveal anymore, as he is only a memory in Homer’s mind. A funny line that is enhanced when spoken in Cash’s Arkansas twang. When asked by Homer whether he should give up his possessions to attain inner peace, Cash snorts with laughter from behind the microphone, telling Homer to get more possessions. The man even acts out the sounds of gnawing on Homer’s leg. Some nice touches that only certain actors would able to add to a line like that.

A bunch of singers have lent their voices to The Simpsons over the years. While this list could also include the individual Beatles members, Linda Ronstadt or Elton John, Johnny Cash rises above the rest in his two minutes of screen time. In fact, I would argue that Johnny Cash is better in his two minutes as the Space Coyote than certain guest stars for whom whole episodes have been built around (Elon Musk).

Mark Hamill- Himself/Leavelle-Mayored To The Mob

With every television show ever produced now either being shown on a random channel or being streamed on a randomly named streaming service coupled with the information given by sites such as Wikipedia and IMDb, it should be no secret to anyone that Mark Hamill is an incredible voice actor. Since first voicing characters for three episodes of The New Scooby-Doo Movies in 1973 and 1974, Mark Hamill has had 190 distinct voice acting roles on film and television. During a similar time, he has performed in 91 live-action movies and television shows. However, to most audiences, he will forever be known as Luke Skywalker. When he appeared on The Simpsons Season 10 episode ‘Mayored To The Mob’, this recognition became the crux of his guest appearance.

In ‘Mayored To The Mob’, Homer becomes Mayor Quimby’s bodyguard. However, he has to protect the mayor from the threat of Fat Tony and his cronies. The episode also sees Mark Hamill (playing himself) bookend the show. He first appears at Springfield’s ‘Bi-Mon-Sci-Fi-Con’, engaging with a crowd of fans who want to ask him about Star Wars. However, a riot breaks out, and Mark, along with Mayor Quimby, is rescued by Homer from the onrushing crowd. Following the incident, Quimby hires Homer as his new bodyguard, setting up the main plot.

Hamill later appears in the third act, playing Nathan Detroit in ‘Guys and Dolls’ at the Springfield Dinner Theatre. In another musical parody that only The Simpsons can offer, Mark Hamill plays Nathan Detroit while swinging a lightsabre and singing about the Star Wars characters. He later helps Homer foil an assassination attempt on the mayor. As well as playing himself, Hamill also plays Leavelle, Homer’s bodyguard instructor.

How was Mark Hamill in this episode? Luminous, magnetic, effervescent. In all seriousness, Hamill is excellent. I only just realised while researching this post that he played Homer’s bodyguard instructor. Hamill is a pro when it comes to playing other people but also plays himself rather well. In 1998, Mark Hamill would have been fair game to refuse this guest role because it involved talking about Star Wars, which he had probably talked about non-stop for the previous 21 years.

However, Mark Hamill is a nice man and is willing to poke fun and laugh at himself. Much of the humour he is involved with has something to do. In fact, Hamill's inclusion in the episode is so that the writing team can satirise Star Wars fandom and poke fun at the public perception of Hamill solely being known for being Luke Skywalker. Mark works well in the straight man role but also gets plenty of laughs of his own. Remember that’s his headshot up there next to the pepper steak, and don't you forget it!

It should not have been a surprise for hardcore animation fans that Mark Hamill would serve as an excellent Simpsons guest star. For those who weren’t, Hamill’s performance served as a pleasant surprise in a great Season 10 episode.

So there is my selection of the best one-time Simpsons guest stars. If you have any other suggestions, do not hesitate to suggest some more. If you want to see a sequel to this story, feel free to drop me a tip below.

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