25. ''The Regina Monologues''
Airdate: Nov. 23, 2003
Episodes of The Simpsons that qualify as all-time classics are rare in the new millennium, but ”The Regina Monologues” has a connection to the show’s golden age: writer John Swartzwelder, the man behind a slew of classic episodes (including five others on this list). His final writing credit, ”Monologues,” takes the family to England in a joke-dense episode filled with allusions to Trainspotting, My Fair Lady, and James Bond, and features a cameo by a sitting head of state (Tony Blair), as well as big-name Brits Ian McKellen and J.K. Rowling. ”The Simpsons are going to ________!” has become a trope on the show, but seldom has it worked so well.
24. ''You Only Move Twice''
Airdate: Nov. 3, 1996
One of the Golden Age’s wackiest episodes also happens to be one of its funniest. In this season 8 standout, the Simpson clan leaves Springfield behind when Homer gets a new job at the Globex Corporation — a mysterious mega-company run by friendly-seeming ginger Hank Scorpio (Albert Brooks, giving his best Simpsons guest performance). Gradually, it becomes clear (to everyone but Homer) that Scorpio’s actually a ruthless supervillain hell-bent on defeating secret agent James Bont. It’s an absurd setup bolstered by one of the show’s best laughs-per-minute ratios. Now, if you’ll excuse us, we have to take a trip to Hammocks-R-Us; it’s in the Hammock District.
23. ''Lisa's First Word''
Airdate: Dec. 3, 1992
The best Simpsons episodes aren’t only hilarious—they’re also poignant, showcasing the big, beating heart beneath the series’ occasionally caustic satire. Nowhere is that more apparent than in the show’s early flashback episodes, including ”The Way We Was,” ”I Married Marge,” and ”And Maggie Makes Three”—the latter of which ends with what may be the most heartwarming image ever seen on TV. Of that stellar quartet, though, ”Lisa” reigns supreme, thanks both to its emotional high points (the titular event, which shines a spotlight on Lisa and Bart’s relationship; its closing moment, in which Maggie (played by guest star Elizabeth Taylor, of all people) says her own first word, ”Daddy”) and its barrage of ace jokes (Bart’s ”spout medley,” ”It’s not easy to juggle a pregnant wife and a troubled child, but somehow I managed to fit in eight hours of TV a day,” ”can’t sleep, clown’ll eat me”).
22. ''Hurricane Neddy''
Airdate: Dec. 19, 1996
Homer’s mild-mannered nemesis had a few spotlight episodes before this one—but none were as juicy as ”Hurricane Neddy,” which digs into just what makes Springfield’s model citizen tick. It all starts when Hurricane Barbara sweeps through town, sparing most residents—except the devout, endlessly generous Flanders clan, who lose everything they own. (Ned doesn’t have insurance because he considers it a form of gambling.) What follows is half an hour of darkly-tinted soul searching in which Ned questions his faith (”I’ve done everything the Bible says, even the stuff that contradicts the other stuff! I’ve even kept kosher, just to stay on the safe side”), finally gives the rest of Springfield a piece of his mind (Moe: ”Hey, I may be ugly and hate-filled, but I… um, what was the third thing you said?”), then checks himself into a mental hospital. One of the series’ darker installments, to be sure—but it’s also relentlessly hilarious and quotable (”I’m Dick Tracy! Take that, Pruneface! Now I’m Pruneface! Take that, Dick Tracy! Now I’m Prune Tracy!’ Take that, Dick…”).
21. ''Who Shot Mr. Burns? Parts 1 and 2''
Airdate: May 21, 1995; Sept. 17, 1995
A two-part comedic homage to Dallas‘s ”Who shot J.R.?” stunt, ”WSMB?” is perhaps The Simpsons‘s most grandiose pop moment ever. An atypical outing, too: Satiric potshots (O.J. Simpson, Madonna, and Twin Peaks) and gut-busting randomness (Moe’s marathon lie-detector session is a classic) are subordinate to a methodically plotted murder mystery that, alas, climaxes with a cop-out, albeit a deliberate one. (Maggie did the deed—accidentally, of course.) There’s no way it could have approached the ratings for the Dallas cliffhanger, but it’s still a pivotal marker in the show’s evolution. By deftly deploying The Simpsons‘s array of supporting characters (even Doctor Colossus!), this onetime anti-Cosby lightning rod demonstrated what a rich, self-sustaining universe it had become.
20. ''Radio Bart''
Airdate: Jan. 9, 1992
Homer tries to top his past gifts to Bart (a shoe tree and shelf paper) with a Mr. Microphone-style radio. The boy immediately drops it down a well and begins broadcasting plaintive cries for help as Timmy O’Toole. A ridiculous media circus ensues: Hucksters sell authentic Timmy baby teeth, and guest voice Sting leads an overblown, ”We Are the World”-style ballad called ”We’re Sending Our Love Down the Well.” In the end, Timmy’s story is bumped off the front page by a squirrel who resembles Abraham Lincoln, and Sting’s ditty gets booted from No. 1 by Funky C Funky Do’s ”I Do Believe We’re Naked.” It’s a media parody so sharp, we’re still stinging a bit.
19. ''Simpsons Spin-off Showcase''
Airdate: May 11, 1997
”Could The Simpsons ever maintain its popularity without Moe the bartender?” asks Troy McClure. ”Let’s hope so — because Moe is leaving to do his own sitcom.” This send-up of spin-offs has it all, from odd pairings (Grampa Simpson’s spirit inhabits a love-tester machine in Moe’s bar) to awkward cameos (says Lisa to Chief Wiggum, newly relocated to New Orleans: ”I can’t wait to hear about all the exciting, sexy adventures you’re sure to have against this colorful backdrop”). But ”The Simpson Family Smile-Time Variety Hour” is the strongest of the three spawn — a searing homage to one of the most dreadful spin-offs ever, The Brady Bunch Hour. The Waylon Smithers Dancers and Hee Haw interstitials are a hoot, but memo to Fox: Don’t be getting any ideas.
18. ''Flaming Moe's''
Airdate: Jan. 21, 1991
Moe laments his poor business: ”Increased job satisfaction and family togetherness are poison for a purveyor of mind-numbing intoxicants like myself.” Then Homer invents a new drink, for which Moe takes credit. The ”Flaming Moe” turns his bar into a raging success (a velvet-rope policy begins, Aerosmith perform ”Walk This Way,” and Moe hires a comely new bartender). ”Flaming Moe’s” is a crucial addition to The Simpsons‘s liquor canon, with a Cheers parody that includes a sobering theme song (”Liquor in a mug/Can warm you like a hug”). Extra attraction: Bart actually apologizes for making a prank call to Moe’s. Remorse and fiery mixed drinks—does it get much better?
17. ''Itchy & Scratchy Land''
Airdate: Oct. 2, 1994
Based on those cartoonishly violent killer critters, Itchy & Scratchy Land is the theme-park realization of Bart’s most extreme daydreams — no wonder he and Lisa beg to go there for a family trip. What’s waiting for the Simpsons when they arrive—besides two gargantuan parking lots, of course—is actually a smart riff on the Disney empire: There are shots at Walt’s lame character spin-offs (Klu Klux Clam, anyone?), a dig at his speculated sordid past (Itchy & Scratchy’s creator turns out to be a Nazi sympathizer), and a nod to the park’s mollifying grown-up attractions (the booze-filled ”Parents’ Island”). When the animatronics attack, the showdown between man and machine—okay, Homer and a giant robot mouse—is an uproarious rebuttal to capitalism run amok.
16. ''Homer at the Bat''
Airdate: Feb. 20, 1992
When Mr. Burns recruits nine all-star major-leaguers for his company softball team, what ensues is less an indictment of America’s pastime than a loopy celebration of the sport’s long-lost innocence, a paean to pro sluggers as both heroes (Jose Canseco misses the big game because he’s rushing into a burning house to rescue a baby—and a cat, and a player piano…) and softies (Darryl Strawberry sheds a tear at Bart and Lisa’s bleacher heckling). It was also early proof that The Simpsons could juggle a squad of guest stars without giving the family short shrift: Who drives in the winning run when a ball bounces off his head? Homer, of course.
15. ''Twenty-Two Short Films About Springfield''
Airdate: April 14, 1996
Working with animation grants the writers of The Simpsons the liberty to do things that live-action shows can only dream of. They can create a supporting cast that’s several dozen characters deep and produce episodes that rely on elaborate concepts rather than on straightforward plots. ”Twenty-Two…” plays to these strengths. Taking its title (if nothing else) from the movie ”Thirty-two Short Films About Glenn Gould,” the outing is a Whitman’s Sampler of Springfieldians, giving such fan favorites as Snake, Chief Wiggum, and Dr. Nick Riviera their brief moments at center stage. (It even finds time to supply the hillbilly Cletus with a toe-tapping theme song.) If that’s not enough, it wedges in a priceless ”Pulp Fiction” parody, replete with a nuanced discussion of the difference between Krusty Burger and McDonald’s. Let’s see a Chuck Lorre joint try that.
14. ''The City of New York vs. Homer Simpson''
Airdate: Sept. 21, 1997
The show that dares ask the question ”Why did I drink all that crab juice?” A bingeing Barney ditches Homer’s car in the Big Apple, prompting a family trip to retrieve it. Change-of-venue episodes are typically uninspired, but this ”City” is frantically busy — skewering foreign-food vendors (five words: Khlau Kalash on a Stick), crazy subway dudes, and gawking tourists. A Broadway parody about the Betty Ford clinic called Kickin’ It is uncomfortably catchy; even bits about the Twin Towers are so clever, you’ll smile instead of wincing. Plus, Marge offers an admonition for anti-Gothamites: ”Of course you’ll have a bad impression of New York if you only focus on the pimps and the C.H.U.D.’s.” Put that on a T-shirt, and we’ve got something.
13. ''I Love Lisa''
Airdate: Feb. 11, 1993
Lisa gives sad little Ralph Wiggum a Valentine’s Day pity card, featuring a smiling train and a special greeting. ”You Choo-Choo-Choose Me?” marvels a desperately happy Ralph. Anyone who’s suffered an unrequited crush will find these 30 minutes wonderfully squirmy. Lisa ignores Homer’s advice for warding off Wiggum (”Six simple words: I’m not gay, but I’ll learn”) and ends up dumping him live on Krusty’s 29th Anniversary Show (”You can actually pinpoint the second when his heart rips in half,” enthuses Bart, watching in slo-mo). But ”I Love Lisa” ultimately reveals the show’s unexpected sweet side, as when Ralph cheerfully reads a make-up card from a repentant Lisa: ”’Let’s Bee Friends.’ It says ‘bee’ and has a picture of a bee on it!”
Airdate: Feb. 18, 1993
For years, we chuckled at Homer’s sloppy, overheated love for beer. But all that hilarious brain-cell killing was never really addressed…until this episode, in which Homer—riding high on a Duff brewery tour buzz—gets busted for DWI and reluctantly heeds Marge’s request to quit drinking for a month. Not only does ”Duffless” tweak an unrelenting alcohol culture (a billboard flips between ”Friends Don’t Let Friends Drive Drunk” and ”It’s Always Time for Duff”), it deftly depicts poignant, if grudging, emotional growth for Homer: After bemoaning his newfound sobriety at a baseball stadium (”I never realized how boring this game is”), he forgoes a reward beer to bike into the sunset with Marge.
11. ''The Last Temptation of Homer''
Airdate: Dec. 9, 1993
When Mr. Burns is forced to hire a female employee at the plant, Homer is suddenly very attentive at work. There’s plenty Homer admires about Mindy Simmons (voiced to slinky perfection by Michelle Pfeiffer): gluttony, sloth, and, he suspects, outrage that ”’Ziggy”s gotten too preachy!” Of course, we know that Homer will stay faithful, his marriage having already survived Jacques the bowling instructor and a giant catfish named General Sherman. But it’s Homer’s anguished journey (”Oh no, I’m sweating like Roger Ebert!”)—and a memorable cameo by Colonel Klink of Hogan’s Heroes—that makes getting there so great. It’s no Scenes From a Marriage, but it’s a hell of a lot more amusing.
10. ''Treehouse of Horror V''
Airdate: Oct. 30, 1994
Simpsons Truism No. 666: ”Treehouse” episodes are as inconsistent as Grampa’s bladder. Welcome to the exception. ”The Shinning” is a parody brimming with such detail, comic timing (”No TV and no beer make Homer…something something”), and Kubrick send-ups that it ranks with the greatest of pop-culture spoofs. ”Time and Punishment” features Homer’s time-traveling toaster and one of the most beautifully random moments in Simpsons history (Homer: ”Don’t panic. Remember the advice your father gave you on your wedding day.” Grampa in thought bubble: ”If you ever travel back in time, doooooonnnn’t step on anything…”). Maybe ”Nightmare Cafeteria” doesn’t shine as brilliantly, but we think it’s perfectly, well, ”cromulent.”
9. ''Mr. Plow''
Airdate: Nov. 19, 1992
”Call Mr. Plow, that’s my name/That name again is Mr. Plow!” Those 12 words of insipid brilliance stand testament to one of the few times Homer has actually succeeded at something. As Springfield’s No. 1 snow mover, Homer—rather incredibly—earns some extra money, the gratitude of Mayor Quimby, and the amorous adoration of Marge (She: ”Would you mind…?” He: ”Cutting my nails? Brushing my teeth?”). But Homer finds competition—and even betrayal—from…Barney? A curiously dark episode (we learn that Homer is responsible for Barney’s alcoholism) in which escalating tensions come to a head on icy Widow’s Peak. Not exactly laugh-a-minute, but oh, that jingle…
8. ''The Itchy & Scratchy and Poochie Show''
Airdate: Feb. 9, 1997
Hey, kids! Who likes scathing commentary on aging TV series? In this provocative, self-referential spectacle that polarized a nation (okay, some particularly rabid fans), Itchy & Scratchy‘s falling ratings prompt the network suits to introduce a painfully overhip canine. (”You’ve heard the expression, ‘Let’s get busy’? Well, this is a dog who gets biz-zay.”) The Homer-voiced Poochie provides perfect fodder for aggressive meta-lampoonery: As Lisa criticizes the desperate character-adding act, a hipster teen named Roy is seen inexplicably chillin’ with the Simpson clan. No cow is sacred here, not even The Simpsons‘s increasingly nitpicky fans, who are milked for laughs in the Comic Book Guy’s ”Worst Episode Ever” didacticism. Worst ever? Hardly.
7. ''Homer's Phobia''
Airdate: Feb. 16, 1997
The Simpsons gets away with more hot-button hotdoggery than any other show, and the most cunning example may be this flamboyant installment, in which the family befriends John (John Waters), the droll owner of a kitschy collectibles shop… until Homer finds out that he’s gay. For a man who once called a spoon ”the metal dealie…you use…to dig…food,” Homer attains a new level of keg-headedness in his foolish paranoia (”He didn’t give you gay, did he?”) and absurd anger toward John for not mincing around and declaring his orientation (”You know me, Marge—I like my beer cold, my TV loud, and my homosexuals fa-laaaming!”). But the same-sex silliness never turns offensive, perhaps because of the sincere subtext: By worrying that John is going to convert Bart, Homer actually fears that he hasn’t been a good father—thus explaining the accidental visit to the gay steel mill. Hot (and funny) stuff, coming through!
6. ''Lisa the Vegetarian''
Airdate: Oct. 15, 1995
In the early days, Bart and Homer were the Simpson family’s — and the show’s—undisputed breakout stars. Talk to Simpsons writers, though, and you’ll discover something interesting: A critical mass name Lisa—nerdy, earnest, principled, perpetually misunderstood Lisa—as their favorite Simpson of all. Which means this list needs a Lisa episode—and not a Lisa episode that’s really a Bart episode (”Lisa’s First Word”) or a Lisa episode that’s really a Ralph episode (”I Love Lisa”). (Don’t agree? Go back to Russia!) And which Lisa episode is better than ”Lisa the Vegetarian,” in which the smartest kid in Springfield first realizes the unsettling connection between the lamb she just met at a petting zoo and the chops Marge is serving that very night? But there’s more to this half-hour than Lisa’s awakening; her meat-eschewing highlights her relationship with Homer, one of the show’s most interesting dynamics, and also leads to a few of the series’ catchiest gags. Sing it with me now: You don’t win friends with sal-ad!
5. ''A Fish Called Selma''
Airdate: March 24, 1996
You may remember Troy McClure from such TV shows as ”The Simpsons 138th Episode Spectacular,” but in his splashiest turn, the underemployed actor is plagued by a ”romantic abnormality.” ”Gay? I wish!” says the closeted fish fetishist, who becomes a family man by marrying Marge’s sister Selma (the one with a repetitive stress injury from scratching her butt). Hollywood lampoons are well-tread ground for the show, but this take on the scandal-contrition cycle, featuring the wonderful McClure vehicle Stop the Planet of the Apes, I Want to Get Off!, is particularly smart. And Selma’s farewell to McClure is also a touching tribute to the man who supplied his voice, the late Phil Hartman: ”Goodbye, Troy. I’ll always remember you, but not from your films.”
Airdate: Oct. 21, 1993
It begins with Citizen Kane, ends somewhere near the ”Planet of the Apes,” and in between, manages to find time to include Hitler, the Ramones, and 64 slices of American cheese. But despite being one of The Simpsons‘s most spectacularly overstuffed episodes, ”Rosebud” has plenty of heart, though it is the Mephistophelian ticker belonging to Mr. Burns, who, on the eve of his birthday—somewhere north of 100—finds himself pining for Bobo, his long-lost teddy bear. Burns and Smithers’ efforts to retrieve the tattered toy from Maggie show why they’ll always be TV’s most functional dysfunctional couple: Smithers (who fantasizes about his boss jumping out of a birthday cake) isn’t happy unless his boss is happy—which happens only after an empathetic Maggie gives Bobo up. It’s a moment that proves even Springfield’s twisted billionaire can learn to love—though he conveniently forgets how a few seconds later.
3. ''Last Exit to Springfield''
Airdate: March 11, 1993
This episode is virtually flawless, the product of a series at the height of its creative powers—when the satire was savage and relevant, when names like John Swartzwelder, George Meyer, and Conan O’Brien were relatively unknown, when Maude Flanders lived. So it is that we find America’s favorite family at Painless (formerly ”Painful”) Dentistry, because Lisa is in need of braces. Meanwhile, at the nuclear plant, Mr. Burns is trying to ax the union dental plan. The rest is the stuff of syndication legend: Burns facing down ”brilliant” labor kingpin Homer Simpson; Homer Simpson facing down his own brain (”Lisa needs braces/DENTAL PLAN!”); Grampa rattling on about wearing onions on his belt. ”Last Exit” is a glorious symphony of the high and the low, of satirical shots at unions and sweet ruminations on the humiliations of adolescence (as evidenced by Lisa, who copes with a medieval mouth contraption), and, of course, all those ”D’oh!”s. The things, in other words, that make us love The Simpsons in the first place.
2. ''Cape Feare''
Airdate: Oct. 7, 1993
The Simpsons is, at its heart, one big parody, but even Homer Thompson could recognize ”Cape Feare” as the show’s most meticulous and manic pop-culture takeoff. Not only is it a pitch-perfect send-up of the Martin Scorsese remake (with Kelsey Grammer’s Sideshow Bob traveling to Terror Lake to hunt down and murder his pint-size nemesis, Bart), but it also features one of the most bizarre scenes in television history. We’re referring, of course, to the rakes. Think about it. How many other series would waste valuable prime-time real estate by showing a man whacking himself in the face with a garden rake not once, not twice, but NINE TIMES?!? If ever there was a gag genius in its repetitive stupidity (progressing from funny to not so funny to the funniest thing ever), this is it—merely the sharpest cut in an entire episode that just plain kills.
1. ''Marge vs. the Monorail''
Airdate: Jan. 14, 1993
Fast-talking huckster Lyle Lanley (Phil Hartman, natch) sells the town a faulty monorail; only through Marge’s intervention is the town saved. That’s the plot of ”Marge vs. the Monorail,” but it’s not the point. The point is that the episode has arguably the highest throwaway-gag-per-minute ratio of any Simpsons, and all of them are laugh-out-loud funny. You want parodies? In its first five minutes, ”Monorail” skewers The Flintstones, Beverly Hills Cop, The Silence of the Lambs, and Batman. Celebrity cameos? Leonard Nimoy bores the town with tales from the Star Trek set. Simpsons in-jokes? Country star Lurleen Lumpkin, from ”Colonel Homer,” has a bit part. A musical number? The Music Man‘-inspired ”The Monorail Song” is, well, inspired. Elaborate visuals that were clearly devised by a roomful of overgrown boys? This episode features giant remote-controlled mechanical ants, a radioactive squirrel, an escalator to nowhere, and—in case we haven’t mentioned it already—Leonard Nimoy. Thus we proclaim: Best. Episode. Ever.