In early 2025, Fox renewed its most successful series ever, The Simpsons, ensuring the show will reach its 40th season. The titular family became a cultural institution almost immediately, and Springfield, USA, remains replete with an iconic and beloved supporting cast. So, it might be surprising to learn that arguably the best side character on The Simpsons appeared in only a single episode nearly 30 years ago.
With hindsight, Season 8, Episode 23, “Homer’s Enemy” exists “early” in The Simpsons’ run. However, in 1997, the show was already one of the biggest and most popular sitcoms on television. In fact, it was so popular that three Hollywood legends were almost cast as Frank Grimes, a side character who appeared just once but never left the hearts and minds of fans. Frank, or “Grimey” as he liked to be called, is a legendary figure in the legacy of the show. However, his introduction and existence proved, at first, to be extremely controversial and important to the show’s legacy.
Frank Grimes and ‘Homer’s Enemy’ Came at a Pivotal Time in The Simpsons’ History
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At the start of the eighth season, worries that The Simpsons were going stale and could face cancellation were ever-present. Executive producers Bill Oakley and Josh Weinstein wanted to make sure they and the writers prevented that from happening. With a successful television series, many producers take the “if it ain’t broken, don’t fix it” approach, lest any changes meant to improve things drive viewers away. Instead, they encouraged the writers to craft episodes of The Simpsons that broke conceptual boundaries.
In both interviews about the episode and on a DVD commentary track, writer John Swartzwelder explained the thinking behind “Homer’s Enemy.” He conceptualized Frank as a “regular guy” with a strong work ethic and sense of order, forced to endure Homer Simpson. At first, Frank is a sympathetic character whose reactions serve to deconstruct how time changed Homer and The Simpsons in general. By the end, Frank turns cruel, becomes an antagonist, and ends up dead.
The look of Frank Grimes was inspired by Michael Douglas’s character in the film Falling Down, a guy whose white male grievance at a changing multicultural society becomes an excuse to murder and terrorize people. The episode also features a subplot where Bart buys a decrepit factory at auction, included to lighten the episode. It also serves as a kind of mirror to Homer’s and Frank’s story, with Milhouse in the latter’s role but unbothered by the buffoonery.
Why Frank Grimes Was a Controversial Character Among The Simpsons Fans at First
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The episode begins with a news story about Frank Grimes, specifically his cartoonishly difficult life. He was abandoned on a highway by his parents at the age of four. He never went to school because he had to work as “a delivery boy delivering toys to more fortunate children.” On his 18th birthday, he got caught “in a silo explosion” and had to teach “himself to hear and feel pain again” during his “long recovery.” Still, he took correspondence courses in science and engineering and eventually graduated, the reason for the news report.
Mister Burns tells Smithers to hire Frank as his executive vice president at the power plant, seemingly moved by Frank’s story. Of course, when Smithers brings Frank to him, Burns had just finished watching a story about a dog. He gives the VP job to the dog — seen a few more times in the episode — and tells Smithers to “put him somewhere out of the way.” He ends up working with Homer, and he quickly grows to despise him. From his lack of work ethic to Homer’s beautiful family and expensive home, Frank resents Homer calling him “everything wrong with America today.”
What made Grimes one of The Simpsons’ most controversial characters, however, is the way Homer reacts. He is deeply dismayed at how much Frank dislikes him, while still remaining oblivious to his own behavior. He invites Frank to dinner at their home, and he even got lobsters to try to impress him. His guest arrives, unaware that it was a dinner invitation, and Homer’s attempt to befriend him only makes him angrier. Frank also gets the blame and a pay cut after knocking a vial of acid out of Homer’s hand (which he was about to drink), which destroys a wall.
The combination of Homer’s desperation and just how awful Frank’s life was seemed more sad than funny. Critics of “Homer’s Enemy” consider it one of The Simpsons‘ most disturbing episodes, especially given its dark ending. Some viewers and critics felt the tragedy robbed the episode of any humor. However, many others think it did exactly what the producers wanted from Season 8. Conceptually, it satirized the exaggerated characters and situations in TV comedy and the show itself.
What Makes Frank Grimes One of the Best Single-Episode Characters on The Simpsons
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Ironic considering the show’s longevity, Frank is one of the few characters on The Simpsons who only appear once, which is largely why he stands out. When no big stars won the role, series regular Hank Azaria stepped in to do the voice. Still, the veteran voice actor received more guidance from producers to shape his performance, according to the episode commentary.
Azaria cited actor William H. Macy as his inspiration because of the way the character actor balances soft-spoken, calm, and intense passion in his line delivery. He called it “the most emotional” and role he “worked on the hardest.”
Frank is also remarkably complex, relatively speaking. His complaints about Springfield and Homer specifically are not without good cause. In this episode, Homer is particularly genuinely terrible at his job, and no one cares. In fact, Frank was prescient, given the evolution of the character over the next 30 seasons. There is even a theory Frank Grimes inspired “Jerkass Homer,” the term used by fans to describe the character’s devolution from a kind, lovable dunce into, well, a jerkass.
The great thing about Frank Grimes is that he can appeal to fans who adore The Simpsons as well as those who feel the series haslost its magic. Sure, his gripes are technically correct, but (Schwarzenegger voice) that’s the joke. It’s a cartoon where exaggeration and nonsense are part of its makeup. The Simpsons is “about a town of good-natured dum-dums dealing with a changing world, yet our characters never really change,” according to Executive Producer Matt Selman, who joined the show the same year “Homer’s Enemy” debuted.
With Just One Episode, Frank Grimes Is a Huge Part of The Simpsons’ Legacy
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Technically, it’s incorrect to say that Frank Grimes only appeared on The Simpsons one time. He returned in at least three “Treehouse of Horror” episodes as a ghost or monster. Beyond this, the show will make references to him every so often, even showing his gravestone. (His epitaph is “Homer’s Enemy.”) In one of the first episodes marking Sideshow Bob’s transition from villain to punchline, Frank Grimes, Jr. keeps trying to kill Homer as revenge for his father. Hilariously, when Homer learns this, he asks, “How is ol’ Grimey?”
With over 35 completed seasons, The Simpsons inspired more than one generation of writers, animators and humorists. Even though he appeared in just one episode, Frank is no different. In the kind of perfect synergy it would be impossible to plan, he’s partially responsible for one of the most disliked villains in the Marvel Cinematic Universe. Writer Jeff Loveness revealed Frank Grimes inspired M.O.D.O.K. in Ant-Man and the Wasp: Quantumania. To him, Darren Cross is ” this really put-upon, selfish, entitled but then also deeply sad, insecure man who knows that he got a sh– deal in life and is trying to make the best of it.”
While the controversy around “Homer’s Enemy” softened with time, it’s not fully gone. In 2007, Mike Reiss, a former executive producer on The Simpsons, told The Bristol Press it was one of his least favorite episodes, thinking it “was in bad taste.” In 2021, Swartzwelder said it was one of his favorite episodes of the show, and “Homer’s Enemy” often lands among the series’ best in retrospectives, ranked lists or critical analyses. Not bad for a goofy character who existed in this universe for a mere 22 minutes.
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Release Date
December 17, 1989
Network
FOX
Directors
Steven Dean Moore, Mark Kirkland, Rob Oliver, Michael Polcino, Mike B. Anderson, Chris Clements, Wes Archer, Timothy Bailey, Lance Kramer, Nancy Kruse, Matthew Faughnan, Chuck Sheetz, Rich Moore, Jeffrey Lynch, Pete Michels, Susie Dietter, Raymond S. Persi, Carlos Baeza, Dominic Polcino, Lauren MacMullan, Michael Marcantel, Neil Affleck, Swinton O. Scott III, Jennifer Moeller
Writers
J. Stewart Burns, Michael Price, Brian Kelley, Bill Odenkirk, Dan Vebber, Kevin Curran, Stephanie Gillis, Dan Castellaneta, Deb Lacusta, Billy Kimball, Jessica Conrad, Cesar Mazariegos, Daniel Chun, Jennifer Crittenden, Conan O’Brien, Valentina Garza, Elisabeth Kiernan Averick, Christine Nangle, Broti Gupta, Loni Steele Sosthand, Megan Amram, Bob Kushell, David Isaacs, David Mandel
Franchise(s)
The Simpsons
Dan Castellaneta
Homer Simpson / Abe Simpson / Barney Gumble / Krusty (voice)
Julie Kavner
Marge Simpson / Patty Bouvier / Selma Bouvier (voice)