Although “Homer’s Enemy” is still the darkest episode ofThe Simpsonsever, this is precisely what makes it the show’s highest-rated outing, too. With more than 790 episodes and a theatrical movie spinoff to its name,The Simpsonsis officially the longest-running scripted primetime American TV show in history.

As such, it is tough to name the show’s best episode ever, and any attempt to do so is sure to result in wars among fans, critics, and commenters. That said, there are some episodes ofThe Simpsonsthat are considered masterpiecesby everyone familiar with the show. Most of these are particularly ambitious, inventive outings.

Frank Grimes in The Simpsons

Season 3, episode 17, “Homer at the Bat,” juggles no less than nine subplots while still focusing on Homer’s central journey. Season 5, episode 2, “Cape Feare,” is ashot-for-shot parody of Martin Scorsese’sCape Fearremake that features some of the show’s most inspired standalone gags ever.

However, one outing stands out among even a list of the best episodes ofThe Simpsons, and it is a notably dark one. Unlike a lot of these other classics, season 8, episode 23, “Homer’s Enemy,” has a disarmingly simple premise. A new colleague begins working with Homer and takes an intense dislike to him.

Frank Grimes' funeral in The Simpsons

“Homer’s Enemy” Is The Highest-Rated Episode of The Simpsons On IMDb

Season 8 Episode 23 Boasts A Series-High Rating of 9.3

Technically, that’s all there is to the story of “Homer’s Enemy.” Unlike “Lemon of Troy” or “Treehouse of Horror V,” this isn’t a uniquely fast-paced, punchline-packed episode that is filled with constant gags and twists. Instead,“Homer’s Enemy” tells the darkest story in the history ofThe

Simpsons, and, in the process, earned the show’s highest-everIMDbrating.

“Homer’s Enemy” boasts a series-high rating of 9.3 onIMDb, one that isn’t matched by another episode in the series. Although there were a handful of 9.2 episodes and a few rated 9.1, only this John Schwartzwelder-penned outing managed to earn the top spot. Ironically, “Homer’s Enemy” was fairly divisive upon its original release.

Frank, or “Grimesy” as Homer affectionately dubs him, resents Homer’s ability to shirk responsibility at work.

Frank Grimes with his hands on his head in The Simpsons episode Homer’s Enemy

The episode tells the tale of Frank Grimes, a hard-working striver who is horrified by Homer’s incompetence, complacency, and apparently superhuman luck. Frank, or “Grimesy” as Homer affectionately dubs him, resents Homer’s ability to shirk responsibility at work. This is only exacerbated when he sees Homer’s beautiful home and meets his happy family.

Frank Grimes’ Story Is The Darkest Episode of The Simpsons Ever

The Grim Storyline Ends With Grimes’ Untimely Death

WhileThe Simpsonslater flipped this storywith a plot about a character who wanted to actively emulate Homer, Grimes’s story was uniquely dark for numerous reasons. The reality is that, as an absurdly flawed, outlandishly buffoonish cartoon protagonist,Homer often causes his own problems inThe Simpsons.

Homer can be greedy, thoughtless, small-minded, intolerant, lazy, and mean-spirited, and everyone from his neighbors to his wife generally accepts his flaws with perpetual grace. This means that, if viewers ever encountered the character in the real world, Homer would probably be pretty insufferable. He has been insulated from consequences for years and has grown used to this cushy existence.

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Of course, the only reason Homer is so flawed is that it is these same qualities that make him relatable. WhileThe Simpsonshas famously predicted the futurenumerous times, the show didn’t become a global pop culture phenomenon because of its ability to tell viewers what was going to happen.

Season 11, episode 17

“Bart to the Future,”

A gag about Donald Trump becoming President of the United States

Season 3, episode 14

“Lisa the Greek"

Season 17, episode 10

“Homer’s Paternity Coot"

Homer’s near-death experience resembles 2023’s Titan submersible implosion.

Homer is a legendary TV character because he epitomizes the worst sides of every average viewer, but he is beloved by his family, his community, and his friends because he still has a heart of gold. Homer is ultimately well-meaning, even if his flaws are almost impressively obvious. It is this that makes Grimes’s story so bizarrely compelling.

“Homer’s Enemy” is effectively the story of a normal person showing up in a sitcom versio of reality. Instead of finding Homer’s foolishness funny, Grimes finds it terrifying since it endangers the entire nuclear power plant’s staff. Instead of laughing along with Homer’s idiocy, Grimes tries to sound the alarm on his negligence.

The Simpsons’s Highest-Rated Episode Highlighted The Show’s Dark Underlying Reality

The Frank Grimes Story Brought Reality To Springfield

“Homer’s Enemy” eventually kills off Frank Grimes in a death that could not be more karmically fitting. Attempting to offer an example of Homer’s idiotic behavior, Grimes fatally electrocutes himself while claiming he will not be harmed, “Because I’m Homer Simpson!”

WhileThe Simpsonshas been criticizedfor its static characters and their unchanging personalities, “Homer’s Enemy” effectively addresses and debunks these critiques. By showing viewers what it would look like if someone tried to bring reality to Springfield, Grimes’s story proves that this would be folly.

Per series writer Josh Weinstein in an interview on the fansiteNoHomers, “We wanted to do an episode where the thinking was, ‘What if a real-life, normal person had to enter Homer’s universe and deal with him?”… It really feels like what would happen if a real, somewhat humorless human had to deal with Homer…. We wanted to show that in real life, being Homer Simpson could be really dangerous and life-threatening.”

The funny thing is,Grimes is still not a hero in “Homer’s Enemy.”The show does depict his fate as tragic, and the sight of Homer’s colleagues and friends laughing at Grimes’s funeral is clearly intended to be a dark joke. However, Grimes’ ultimate comeuppance doesn’t prove he was right about Homer.

Thebiggest problem withThe Simpsonsis the show’s outsized impact on pop culture. The series has been around for so long that everything fromBob’s BurgerstoFamily Guy, toKing of the Hill, toAmerican Dadnow has a flawed but lovable American cartoon father figure of their own, all of them owing at least something to Homer.

As such, the show’s formula should be well outdated by now. However, if “Homer’s Enemy” proves anything, it is that the show’s setup will never truly become obsolete. Homer will always be insulated from criticism by his cartoon reality, since this is what keepsThe Simpsonsfunny even in its fourth decade.

The Simpsons

Cast

The Simpsons is an animated series set in the fictional town of Springfield, following the daily lives of the Simpson family—Homer, Marge, Bart, Lisa, and Maggie. Premiering in 1989, the show is renowned for its satirical commentary on politics, media, and American culture, featuring numerous celebrity guest appearances.