1. LAST EXIT TO SPRINGFIELD (pictured)
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.
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!