“The Simpsons” at 500 — our favorite episodes

The Simpsons airs its 500th episode Feb. 19 at 8pm ET/PT on FOX, as part of its 23rd season (and it will be running through at least Season 25, and Episode No. 559). By now, its longevity, and the numbers and records it keeps racking up year after year, are no longer surprising. It’s become one of those things that is just always there. To an entire generation of viewers, it always has been there; and even to those of us who were around pre-Simpsons, it honestly has become hard to remember that long-ago period, when Homer and his family and friends weren’t around to hold a mirror up to our society’s foibles.


Looking back over the series’ 500 episodes and picking out one’s favorites might be a generational thing as well. The three of us (me, @ChannelGuideRAB and @ChannelGuideSRH) who compiled this list of our favorites are of about the same Gen X age range, and ended up with a list of episodes from roughly the first third of the show’s existence. Whether that says more about the series or us can be debated, but for now, here are our picks of the must-see Simpsons episodes out of its first 500. We’ll be in touch again when the series hits No. 1,000.

Homer at the Bat (Episode 52)
Mr. Burns stocks his nuclear power plant’s softball team with ringers in this classic episode that really brings home just how long The Simpsons has been on the air. The ringers Burns hires at the plant so they can play on the team are a who’s-who of early ’90s MLB stars now well past their playing days (and a couple since tinged with infamy), including Roger Clemens, Wade Boggs, Ken Griffey Jr., Steve Sax, Don Mattingly, Ozzie Smith, Darryl Strawberry, Jose Canseco and Mike Scioscia (all voicing themselves). After most of the pro-ballers begin experiencing freak injuries that keep them out of the big game (“Good Lord! Gigantism!” exclaims Dr. Hibbert upon looking at Griffey Jr. in one scene), it’s up to the actual employees to fill in and play, along with “Daaaaaryl” Strawberry, who remains injury-free, but still subject to a hurtful chant in the outfield.

Rosebud (Episode 85)
In a parody of Citizen Kane, Mr. Burns longs for his childhood Teddy bear, Bobo. After a long, amazing journey through the decades, Bobo ends up the property of Maggie Simpson. Mr. Burns goes to extreme lengths to force the Simpsons to give up the bear. Highlights include the Ramones singing their rendition of “Happy Birthday” to Mr. Burns and Homer staying up all night eating 64 slices of American cheese.

Lisa on Ice (Episode 111)
Sibling rivalry gets ratcheted up when Lisa shows to be an excellent hockey goalie and squares off against Bart’s team. Just about everything you need to know about Homer can be summed up when he instructs, “Lisa, if the Bible has taught us nothing else — and it hasn’t — it’s that girls should stick to girls’ sports, such as hot oil wrestling, foxy boxing and such and such.” Also provides one of Ralph Wiggum’s greatest moments: “Me fail English? That’s unpossible.”

Homer Badman (Episode 112)
This episode shows how timeless The Simpsons’ satire can remain. First aired over 17 years ago, in the wake of the media frenzy surrounding the O.J. Simpson murder case and the dawn of TV tabloid newsmagazine shows, its depiction of the circus surrounding the mistaken allegation of sexual harassment made against Homer by his baby-sitter is perhaps even more timely in today’s era of 24-hour news, in which we are subjected to shows akin to Rock Bottom — the sleazy tabloid show that badly (and hilariously) edits Homer’s story to make him look like a sexual pervert for ratings gold. Before long, the Simpson household is subjected to constant news surveillance and speculation (when Marge lets the cat out, one newsman wonders if it, too, may have been harassed). The episode also features a very funny cameo by Dennis Franz playing Homer in a FOX TV movie very loosely based on the alleged incidents — Homer S.: Portrait of an Ass-Grabber.

Homer the Great (115)
Homer joins the ancient mystic society of The Stonecutters, and it’s soon discovered that he is The Chosen One prophesied to lead them to greatness. But after Homer abuses his power, all his friends abandon him, leaving him all alone to reenact the Civil War with monkeys. Patrick Stewart brilliantly voices the club’s leader, Number One. Includes a great quote that should conclude every gathering: “Now let’s all get drunk and play Ping Pong!”

A Star is Burns (Episode 121)
Usually, crossover shows don’t work too well, but this episode that brings Jay Sherman (voiced by Jon Lovitz) of the animated ’90s series The Critic into Springfield for a film festival ranks as one of the successes. Marge hopes that a film festival will help bring some culture to the town, and she almost gets what she’s hoping for when — of all people — town drunk Barney’s artsy flick Pukahontas (“Don’t cry for me; I’m already dead”) wows the crowd and festival judges (the ones who weren’t bribed into voting for Mr. Burns’ self-indulgent epic, A Burns For All Seasons — directed by Steven Spielberg’s non-union, Mexican counterpart, Señor Spielbergo — that is). But Marge soon regrets putting Homer on the jury when he strongly considers putting his vote toward Hans Moleman’s film, Man Getting Hit by Football. After all, “Barney’s movie had heart, but ‘Football in the Groin’ had a football in the groin.” Moleman also figures in another hilarious scene, when Burns’ film gets booed off the screen by everyone except for Moleman, who apparently is actually saying, “Boo-urns.”

King-Size Homer (Episode 135)
Leave it up to Homer, already at a dangerously high weight, to purposely put on even more so that he can qualify as “hyper-obese” and become able to work at home on disability (and avoid Mr. Burns’ new workplace calisthenics program). That’s the plot of this hilarious episode that features wonderful sight gags (like Homer buying a muumuu in a big man’s store called The Vast Waistband), funny lines (Jimbo Jones’ comment on Homer’s new size: “I hear that guy’s ass has its own congressman!”; Homer’s outrage at the ridicule he receives at a movie theater: “Give me my dignity! I just came here to see Honk If You’re Horny in peace!”) and touching moments (Marge expressing concern for Homer’s health — and her growing lack of attraction toward him).

You Only Move Twice (Episode 155)
Written by Simpsons scribe supreme John Swartzwelder and featuring the voice of Albert Brooks, this episode finds Homer moving his family to a seemingly idyllic town where he will start a seemingly idyllic new job — remaining oblivious throughout the entire episode that his boss, Hank Scorpio (Brooks) is actually a supervillain bent on world domination. James Bond movie clichés are skewered throughout the episode, particularly in the climactic battle in Scorpio’s fortress. At the end, Homer reluctantly has to tender his resignation with Scorpio, and the Simpsons find themselves back in Springfield. After seizing the East Coast, Scorpio sends a still-clueless Homer a parting gift: the Denver Broncos. “It’s not the Dallas Cowboys, but it’s a start.”

The Itchy & Scratchy & Poochie Show (Episode 167)
Some of The Simpsons’ finer episodes have satirized the industry its creative teams know best: the cartoon-making business. This is usually done through the lens of The Itchy & Scratchy Show, the ridiculously violent cat-and-mouse cartoon send-up of Tom & Jerry. In this episode, with ratings slipping for that show, the powers-that-be decide that Itchy and Scratchy need a new character to join them. Seeing as how the animal chain of command goes “mouse-cat-dog,” they decide to add a dog. Not just any dog, but a dog with an attitude. Homer gets the job voicing Poochie, but terrible, overly hip writing (“Catch you on the flip side, dudemeisters!”) for the new character is disastrous, leading to Comic-Book Guy’s famous critique: “Last night’s Itchy & Scratchy was, without a doubt, the worst episode ever. Rest assured that I was on the Internet within minutes registering my disgust throughout the world.” From clueless producers, to market testing, to payment of voice actors, everything is skewered nicely in this episode. And by the way: When are they gonna get to the fireworks factory?

Homer’s Phobia (Episode 168)
After a shop owner (voiced by John Waters) befriends the Simpsons, and they learn he is a homosexual, Homer fears that Bart will become gay in this sendup of cultural stereotypes and prejudices (“I like my beer cold, my TV loud, and my homosexuals fa-laaaaming,” explains Homer at one point). Homer’s desperate attempts to expose Bart to “macho” influences to stave off “gay” are hilarious, especially a trip to a steel mill — which turns out to be owned and operated by gay men, and in fact turns into a gay nightclub in the evening. Unfortunately, as ridiculous as they come across, some of Homer’s paranoid ravings still would not sound out of place in certain areas of society today, 15 years after this episode satirized them (“He didn’t give you gay, did he? Did he?”).

Homer vs. the Eighteenth Amendment (Episode 171)
When Prohibition hits Springfield, Homer finds his calling as the city’s new Beer Baron, and delivers some of his best lines in the series, including “Ah, I’m not gonna lie to you, Marge … So long!” “Gone bowling. Not back, avenge death.” Dave Thomas is terrific as the straight-edge gumshoe Rex Banner, who aims to clean up Springfield, while hopelessly confusing everyone with his command of ‘30s tough-guy lingo: “Where’d you pinch the hooch? Is some blind tiger jerking suds on the side?”

The Simpsons Spin-Off Showcase (Episode 177)
While The Simpsons, to its credit, has not tried to cash in on its success with actual spin-off series, this episode has a lot of fun with “what-if” scenarios of potential spin-offs, all while mocking various lame TV series tropes. Actor Troy McClure (voiced by the late, great Phil Hartman), who you may remember from such TV spin-offs as Son of Sanford and Son and AfterMannix, introduces this collection of three fictional Simpsons spin-offs: Chief Wiggum, P.I., a cop drama that finds Chief Wiggum moving to New Orleans and gaining Principal Skinner as a sidekick on his adventures; The Love-matic Grampa, a sendup of ’60s romantic comedy series in which Grampa Simpson dies and comes back to haunt a love tester machine and help bartender Moe find romance; and The Simpson Family Smile-Time Variety Hour, a parody of those dreadful Brady Bunch variety specials from the ’70s. This episode brilliantly parodies the bad writing and plots of these types of shows.

So what do you think? Like our picks? What are your favorite Simpsons episodes?


Homer at the Bat: © 1992 Fox Broadcasting. ™ and © 1992 TCFFC. All Rights Reserved.

Homer the Great and King-Size Homer: © 1995 Fox Broadcasting. ™ and © 1995 TCFFC. All Rights Reserved.

Homer’s Phobia: © 1997 Fox Broadcasting. ™ and © 1997 TCFFC. All Rights Reserved.


    • Good call on “Coming to Homerica.” We had another fan mention that on our Facebook page.

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