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Top 25 Simpsons Episodes

As ''The Simpsons''' 300th episode approaches, we look back at Homer and Co.'s most hilarious, inspired moments

1. LAST EXIT TO SPRINGFIELD
Airdate March 11, 1993
Here's the thing: ''The Simpsons'' is all about subatomic degrees of brilliance. Is ''Last Exit'' that much better than ''Cape Feare'' or ''Duffless''? Not really. We can't tell you that it has the single best joke or visual gag in the show's history. But we can say that 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. Thus we proclaim: Best. Episode. EVER.

2. ROSEBUD
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''' 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. 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.

4. 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.

5. 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 -- but then 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 here, 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. 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...

7. 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.

8. 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.''

9. 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.''

10. 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 (see No. 21) 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 ''Hogan's Heroes''' Colonel Klink -- that makes getting there so great. It's no ''Scenes From a Marriage,'' but it's a hell of a lot more amusing.

11. DUFFLESS
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.

12. 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 this 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 Simpsons''' 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!''

13. THE CITY OF NEW YORK VS. HOMER SIMPSON
Airdate Sept. 21, 1997
The show 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.

14. TWENTY-TWO SHORT FILMS ABOUT SPRINGFIELD
Airdate April 14, 1996
Working with animation grants ''The Simpsons''' writers the liberty to do things that live-action shows' staffs 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 ''Yes, Dear'' try that.

15. 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.

16. 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''' 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. BART THE DAREDEVIL
Airdate Dec. 6, 1990
The death-defying motorcycle jumps of daredevil Capt. Lance Murdock inspire Bart to jump Springfield Gorge on his skateboard. Attempting to show Bart the danger of the stunt, Homer tries to jump the gorge, and fails. Homer as teacher? Indeed, in ''Daredevil'' we watch the writers in the act of working out Homer's character, balancing selfless and serious with self-serving and slow-witted. His anxiety about getting through Lisa's school orchestra recital to attend Murdock's ''Truckasaurus'' Monster Truck Rally is more in keeping with the lug we know now; Homer hears that the band is playing Schubert's ''Unfinished'' Symphony and says, ''Oh, good -- unfinished. This shouldn't take long.'' Bonus: ''Daredevil'' introduces Dr. Julius Hibbert, who has not yet developed his trademark chuckle.

18. HOMER BADMAN
Airdate Nov. 27, 1994
Years before viewers learned such terrifying terms as ''Lewinsky'' and ''Fox News Channel,'' ''The Simpsons'' aired this fractured take on tabloid media, '90s feminism, and our nation's obsession with gummy candy. Homer is accused of sexually harassing a babysitter -- an ordeal later turned into the TV movie ''Homer S.: Portrait of an Ass-Grabber.'' While defending himself on the newsmag ''Rock Bottom,'' his comments are hilariously edited out of context -- an over-the-top example of our sound-bite-fixated culture. While later seasons overplay Homer's stupidity, ''Badman'' shows him to be a sweet-natured goof; as a brief musical aside shows, he'd rather escape under the sea, ''Little Mermaid''-style, than deal with reality.

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.

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.

21. LIFE ON THE FAST LANE
Airdate March 18, 1990
While ''The Simpsons''' first season seems shockingly tame compared with later, zanier years, the endearing ''LOTFL'' is a showcase for the series' bedrock of character and heart. Furious at Homer for his self-serving birthday gift (a bowling ball -- with his name on it), Marge takes bowling lessons out of spite -- and ends up tempted into an affair with her instructor, the brunch-loving French lady-killer Jacques. ''LOTFL'' is indispensable early ''Simpsons,'' if just for the classic Homerism that caps the happy ending: ''I'm going to the backseat of my car with the woman I love -- and I won't be back for 10 minutes.''

22. HOW I SPENT MY STRUMMER VACATION
Airdate Nov. 10, 2002
You've gotta admire a show that lands the greatest names in rock and then gives them as much respect as a brown M&M. When Homer attends the Rolling Stones' Rock N' Roll Fantasy Camp, corporate Mick howls, ''Rule number one, there are no rules!... Rule number two, no outside food.'' Tom Petty is booed for singing about social issues instead of chicks and cars, and Elvis Costello is called ''Nerdlinger.'' (When Homer knocks off his glasses, Costello wails, ''My image!'') While rockers have always shone in ''Simpsons'' solos, the Stones so giddily mock their hall-of-fame status it makes ''Strummer'' the series' Woodstock: a classic-rock show even Disco Stu could get behind.

23. 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''' increasingly nitpicky fans, who are milked for laughs in the Comic Book Guy's ''Worst Episode Ever'' didacticism. Worst ever? Hardly.

24. SIMPSON AND DELILAH
Airdate Oct. 18, 1990
Check the record books. ''Dawson's Creek'' may claim to have aired network television's first real man-on-man kiss in the year 2000, but back in October of 1990, a serious smooch took place between Homer and his super assistant Karl (voiced by Harvey Fierstein). But lip-locking aside, this early entry -- in which Homer transforms into a ''young go-getter'' courtesy of a hair-growth formula -- is as long on laughs as it is on sizzling sideburns. It's hard to say exactly what makes this well-coiffed installment so special, except to say that it sort of looks like any other ''Simpsons'' episode...only more dynamic and resourceful.

25. WHO SHOT MR. BURNS? PARTS 1 & 2
Airdate May 21, 1995; Sept. 17, 1995
A two-part comedic homage to ''Dallas''' ''Who shot J.R.?'' stunt, ''WSMB?'' is perhaps ''The Simpsons''' 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 ''Dallas''' cliff-hanger, but it's still a pivotal marker in ''The Simpsons''' evolution. By deftly deploying ''The Simpsons''' array of supporting characters (even Doctor Colossus!), this onetime anti-''Cosby'' lightning rod demonstrated what a rich, self-sustaining universe it had become.

Worst Episode: BART TO THE FUTURE
Airdate March 19, 2000
Choosing the lamest ''Simpsons'' episode is like picking the crowning installment of ''Shasta McNasty'' -- it's all relative. So while ''Bart to the Future'' was likely better than anything else on TV the week it first aired, even Mojo the monkey could've banged out a more inventive script: Bart visits an American Indian mystic and foresees Lisa as president and himself as a ponytailed slacker. Plus, the whole looking-into-the-future premise is merely reliving past glory, carried out far more successfully in 1995's ''Lisa's Wedding.'' And you're really in trouble when even Homer -- wasted here as an old man on a wild goose chase for Abe Lincoln's gold -- can't dig up a laugh. We didn't know it was physically possible for something to both suck AND blow.

i've got my discrepencies, as im sure every other fan does, but... this ainta bad list!

Only one episode in the top 25 after 1997,I completely agree.

I concur.

HOMER'S PHOBIA
Airdate Feb. 16, 1997


Zack's personal fav!!!

EVERYBODY DANCE NOW!!

Not a bad list.

Though I would have liked to see the Mister Bergstrom episode on there somewhere... that one was a classic. And the one where Lisa goes to Washington when she won a speech writing contest and ended up exposing a bribe taking senator...

Presactly!

But if I start thinking about exactly what my top 25 would be, I could be here for days... I quoted those two because I saw them again recently and realised once more how great they were. But I'm sure there's dozens more I could name...

My top 25, roughly in the order in which they aired:

Krusty Gets Busted
Two Cars in Every Garage, Three Eyes on Every Fish
Lisa's Substitute
Three Men and a Comic Book
Stark Raving Dad
Homer Defined
Saturdays of Thunder
Flaming Moe's
The Otto Show
Homer the Heretic
Lisa's First Words
Marge vs. the Monorail
I Love Lisa
The Front
Treehouse of Horror IV
Homer and Apu
Lisa's Wedding
Who Shot Mr. Burns? (assuming that they can be merged into one)
Treehouse of Horror VI
Team Homer
22 Short Films About Springfield
Homer's Phobia
The Itchy & Scratchy & Poochie Show
Homer's Enemy
Lisa's Sax

There's about a hundred more that could easily be on this list, of course. Almost everything from seasons 2 through 5 was pure gold.