Pop culture obsessives writing for the pop culture obsessed.
Pop culture obsessives writing for the pop culture obsessed.

In a way, they’re all winners: 10 Simpsons episodes from the past 5 seasons that stand among the series’ best

Illustration for article titled In a way, they’re all winners: 10 Simpsons episodes from the past 5 seasons that stand among the series’ best

1. “The Regina Monologues” (season 15)
De rigueur contemporary opinion dictates that The Simpsons hasn’t been good in at least a decade, and that the show—currently finishing its 20th season—pales in comparison to its golden age from the mid-’90s. Like all generalizations, this one contains some truth, but overlooks evidence to the contrary. Take, for example, “The Regina Monologues”: At first glance, it looks like another addition to the growing line of “The Simpsons are going to ________!” episodes, where traveling to a foreign land provides easy “Boy, Americans sure are assholes!” jokes and riffs on stereotypes. But in the hands of ace writer John Swartzwelder—who penned a staggering list of classic episodes, and the hugely popular “Spider Pig” song from The Simpsons Movie—“The Regina Monologues” rises above the international-episode template. When the family travels to London so Grampa can reconnect with an old love, Homer inevitably ends up in jail for harming the queen, whose H.R.H. designation he claims is the mark of an imposter named “Henrietta R. Hippo.” The episode bursts with great bits, including Bart’s Hockey Dad videogame (“Dad, stop! It’s only assault—don’t make it murder!”), a recurring Bond theme, My Fair Lady and Trainspotting references, and a impressive roster of guest stars that include Prime Minister Tony Blair. Blair took some heat for appearing on the show during the throes of the Iraq War, which the episode addresses in a couple of well-placed barbs from Homer. Classic quote-to-be: “I’m acting the way America acts best: unilaterally!”


2. “Diatribe Of A Mad Housewife” (season 15)
"Diatribe” travels a well-worn path in the Simpsons story arc: Marge as repressed artist, Homer as inconsiderate lout, Homer taking a new job, Flanders as secret hunk. The episode stands out thanks to some particularly funny bits from writer Robin J. Stein, a kids’ TV vet who’s written only one episode, and a pair of stylistic animated sequences. Marge’s first novel, The Harpooned Heart, turns into a bitter commentary on her marriage when Homer gets fired from the plant and takes a job as an ambulance driver. A love triangle develops in the novel when the Marge character (“Temperance Sparrows”) falls for a hunk named Cyrus (a thinly veiled Flanders). The novel takes place during “whaling times,” allowing for some funny commentary on the past (tobacco, Virginia’s miracle plant), and the publishing industry in general. It also has a couple of funny cameos from Thomas Pynchon and the Olsen twins (who read the audiobook version of The Harpooned Heart), though Tom Clancy’s clumsy line-reading doesn’t work as well. Classic quote-to-be: “I didn’t lie! I was writing fiction with my mouth!”

3. “24 Minutes” (season 18)
A spoof on the popular Fox show 24 doesn’t seem a likely candidate for immortality, but if nothing else, “24 Minutes”—co-written by Ian Maxtone-Graham, who’s penned some of the stronger newer episodes, and Billy Kimball—offers a series of funny gags that can sustain the conceit long after people have forgotten about Kiefer Sutherland’s real-time action show. Deep inside the CTU—Counter-Truancy Unit—Lisa, Skinner, and a band of nerds (Martin, Milhouse, Database) track a stink-bomb plot by Jimbo, Dolph, and Kearney. Rogue agent Bart plays the Sutherland role, with Lisa standing in for Mary Lynn Rajskub’s Chloe. (Sutherland and Rajskub appear as well.) The plot unfolds like an episode of 24The Simpsons even copied the show’s split-screen look—but “24 Minutes” is mostly memorable for the jokes that don’t spoof 24: Homer and Milhouse riding a careening Dumpster (“This is our life now, Milhouse. We’re Dumpster folk.”), Jimbo’s mom showing her breast implants to his friends (“Lookin’ good, Carol!” exclaims Dolph), a drill-wielding Moe reading Be Your Own Dentist, the funny Skinner-Chalmers exchanges, and old history books stashed in the air vents (’50s books deemed too racist, ’90s books not racist enough). Of the 24-related material, nothing beats an exceedingly dark sequence that shows Martin, revealed as a mole for the bullies, preparing for his suicide. (Turns out he was just giving himself a wedgie.) Classic quote-to-be: “What is it about a woman in a Dumpster?”

4. “Any Given Sundance” (season 19)
Okay, the film-festival idea has been done before in a classic Simpsons episode (“A Star Is Burns”), and “Any Given Sundance” flagrantly steals its outsider-artist theme, substituting Nelson for Barney. Get over that part, though, and “Sundance” has plenty of hilarious moments: Homer’s imagined film festival (where Mexican filmstrips run from “los DVDs”), the pointed commentary on Sundance, film festivals, and critics, and some good shenanigans from Skinner and Chalmers, who hope Lisa’s documentary will help Springfield Elementary be known for something other than having the highest hamster-mortality rate in town. Throw in a couple funny cameos from Jim Jarmusch (whose Cheaper By The Dozen sequel looks like a real downer) and John C. Reilly, and “Any Given Sundance” stands out as one of Season 19’s best. Classic quote-to-be: “They’re like the family from hell on acid that’s on steroids!”

5. “Kiss Kiss Bang Bangalore” (season 17)
It’s a fool’s errand to pinpoint when and how modern-day Simpsons diverged from its golden age, but one possible culprit is the show’s increasingly frequent tendency to stretch a thin concept way beyond its breaking point. (See: “Bonfire Of The Manatees.”) In that respect, “Kiss Kiss Bang Bangalore” is successful in its restraint: Rather than padding out two admittedly lean plots into a couple of subpar episodes, the writers stuck to separate A and B stories that successfully straddle the line between overblown silliness and timely commentary. The main narrative of Mr. Burns sending the power plant’s operations to India—along with token American employee Homer, who quickly converts the diligent Indian workforce into entitled, casual-Friday-lovin’ layabouts—gets in several digs at both outsourcing and unions, plus a couple of funny, though broad, India-centric jokes, like Homer groaning “Finally!” after finding Apu’s cousin Kavi on the second try in a city of 6 million. Meanwhile, Patty and Selma’s kidnapping of an increasingly needy Richard Dean “MacGyver” Anderson segues from a chuckle-worthy reference to sublime absurdity, culminating with Anderson’s “MacGyver Burgers,” i.e. shredded Slim Jims held together with rubber bands. Classic quote-to-be: “This Olive Garden coupon! It expires at midnight! MacGyver away!”


6. “The Monkey Suit” (season 17)
The Simpsons is frequently at its best when skewering religion, and “The Monkey Suit” goes back to that well with surprising sweetness. After being turned away from the hot new weapons exhibit at the natural-history museum (“Nunchucks: cool, but useless”), Ned Flanders is shocked to learn that evolution has taken over his dear old creationism as the theory of choice in educational circles. When Flanders and Reverend Lovejoy (who’s hoping a controversy will win back his churchgoers from those Episcopalians and their darn vibrating pews) succeed in ousting evolution theory from the curriculum at Springfield Elementary, Lisa is arrested for trying to spread the teachings of “cowardly drunk” Charles Darwin. Her convictions place her at odds with Marge, who is reluctant to choose between science and her beliefs, but she comes around after reading The Origin Of Species (“I can’t wait to see what evolution comes up with next. Maybe a bird with a people face, or a bear with pants on!”), and helps Lisa win the trial by pointing out the striking similarities between evolution’s “missing link” and Homer trying to open a beer bottle. Though it takes a while to get where it’s going (a pre-script featuring Bart trying to cram a summer’s worth of memories into a single day goes on just a little too long), “The Monkey Suit” eventually finds that Simpsons sweet spot at the intersection of family life and social satire. Classic quote-to-be: “Cram it, ya God-wad.”


7. “Papa Don’t Leech” (season 19)
“Papa Don’t Leech” was one of the worst-reviewed Simpsons in recent memory, and was the third least-watched episode in the show’s history, but a lot of that distaste might have been a knee-jerk reaction to the seemingly crass move of dusting off of one of the show’s all-time-great one-off characters, Lurleen Lumpkin (from the season-three stone-cold classic “Colonel Homer”). A second look reveals a solid storyline (courtesy of Reid Harrison, who also penned the great season-eight episode “The Springfield Files”) that stays original while revisiting some of the best parts of “Colonel Homer.” When a broke Springfield calls in its residents’ back taxes, the down-on-her-luck Lurleen becomes a pariah due to her non-payment. The ever-generous Simpson family takes her in, in spite of Marge’s teeth-grinding objections, until she can emerge from her downward spiral. (“I told her not to go into one of those!” Homer says.) Marge makes it her personal mission to reunite the daddy-issue-laden country singer with her deadbeat father. After an initially rose-colored reunion, Royce Lumpkin sells one of Lurleen’s songs to guest stars The Dixie Chicks, who turn in one of the few non-superfluous celebrity cameos in recent memory. Granted, “Papa Don’t Leech” relies heavily on nostalgia, but it does right by its predecessor. Classic quote-to-be: Lou: “Chief, are you okay? Why’d you jump off the roof?” Wiggum: “I just wanted to be extraordinary!”

8. “The Debarted” (season 19)
The Simpsons has wandered into high-concept hell several times over the past half-decade (some might say decade), but “The Debarted” works because its on-the-nose movie-parody elements are anchored in the small-time confines of Springfield Elementary. Rather than tethering this send-up of The Departed to Fat Tony and his gang, the episode centers on one of the show’s time-tested themes: Bart the prankster. When Skinner places an undercover snitch (guest star Topher Grace) in Bart’s schoolyard gang, a nicely paced struggle unfolds between the beleaguered principal and his spiky-haired nemesis. (“Skinner’s five steps ahead of me,” bemoans Bart. “I put a tack on his chair, he’s corked his pants. I throw a tomato, he’s making salad!”) Bringing The Departed into Skinner and Bart’s low-stakes rivalry allows the episode to engage in some fun cinematic styling—such as a nicely done chase scene in which Bart is foiled by two men carrying a “Branson’s View Blockers”-brand opaque panel—without seeming overblown. The B-plot, featuring Homer indulging in the joys of a luxury loaner car while his is in the shop, is similarly down-to-earth, a nice break from the oh-so-wacky shenanigans of the increasingly buffoonish family patriarch. Classic quote-to-be: “The rat symbolizes obviousness!”


9. “Homer And Lisa Exchange Cross Words” (season 20)
The more things change, the more things stay the same, and no matter what else happens on The Simpsons, Homer and Lisa will always be at odds. Many of the show’s best episodes, like “Lisa The Vegetarian,” were born out of the conflict between his oblivious buffoonery and her unwavering do-gooderness. Much of that tension has fallen by the wayside in later episodes, due mostly to the writers’ decision to have Homer do stupid things seemingly for the sake of being stupid, but “Cross Words” is a return to form—a reminder that Homer, at his essence, is still a well-meaning guy. In this mid-season episode, Lisa discovers an innate ability for crossword puzzles and makes it to the final round of a competition; Homer, flush with cash from his business of breaking up couples, bets against Lisa and wins. But while Lisa should be livid, she just… isn’t, which is even more unsettling for Homer. Homer later redeems himself—thanks to guests Will Shortz and Merl Reagle—and the result demonstrates that geeked-out, character-based episodes still hold the most water. Classic quote-to-be: “Here’s your money, drenched in your daughter’s tears.” “You know, for a bartender-bookie, you’re awfully judgmental.”

10. “Gone Maggie Gone” (season 20)
Say you’re The Simpsons, and you’ve done just about everything under the sun in 20 years of existence. It’s time to go bigger, with a riff on The DaVinci Code that feels original and maintains the show’s sense of humor. An eclipse passes over Springfield, and Marge burns her eyes by looking at it directly. This renders her useless around the house, leaving Homer to pick up the slack, a role he’s obviously unprepared for—before long, rats have taken over the kitchen. He heads to the store with Maggie and Santa’s Little Helper to purchase rat poison, and learns that he can’t leave Maggie alone with the stuff, nor can he have the dog and the baby sit unsupervised. And he needs to get across a river, with a boat only big enough for him and one other thing. What’s he to do? Well, the show poses the puzzle to the audience before cutting to commercial, a tack they take during the remainder of the episode—Lisa solves riddles and anagrams (she’s gotten a lot better since the days of “Jeremy’s Iron”) to decipher the mystery of a jewel with the power to bring peace to Springfield. It’s a pretty far-out episode (it includes plenty of alternate history, and at least one journey to hell), but the show can stand to shake things up every once in a while. Classic quote-to-be: “I joined the Freemasons before it was trendy. That’s my eyeball on the dollar bill. That’s also my pyramid.”