Modern-Day Simpsons: 22 Episodes Worth Watching

Earlier this year, The Simpsons kicked off its latest season. Its thirty-first, to be precise.

Though I’ve been watching the show since childhood, I’m continually amazed when each new season begins: “It’s been on how long?” In 2009, the show broke the record as America’s longest-running scripted series (previously held by Gunsmoke), and last year, it broke the record for most episodes ever produced for a scripted series (previously held by… Gunsmoke). And in 2021, The Simpsons will become the longest-running sitcom in the world.

But with each mention of the show’s immortality, someone invariably brings up the caveat. “The Simpsons isn’t funny anymore. It hasn’t been funny since the ‘90s.”

I’ve heard that complaint a thousand times, and I sort of understand it. Though the show is my favorite sitcom ever, and I continue to enjoy it every week, most Simpsoniacs agree that the show’s best years are long behind it. The last true “classic” season was arguably its eighth, which aired over twenty years ago.

But still, I continue to attest that modern-day Simpsons is not bad. Though the series has had some rough spots over the years, it continues to be one of network TV’s most enjoyable and innovative shows. It maintains its heart in addition to its humor, and the characters never go out of style.

And yes – every so often, the show still produces a terrific episode, one that could comfortably fit in alongside the classic years. Once in a while, the show still does something fresh and new, often to great success.

You think I kid? You think I’m attempting to sing the praises of a show that, for twenty-odd years has had all the depth of “Football in the Groin”? Not at all.

I’ve gone through the last twenty-two seasons and picked out one episode from each. These are not necessarily the twenty-two “best” episodes of the show’s post-Golden Era, but they are meant to demonstrate that, even in its weakest years, The Simpsons remembered how to be The Simpsons. String the following 22 episodes together, and I daresay you have a “season” that can rival the show’s finest years. With the first thirty seasons now streaming on Disney Plus, there’s no better time to discover some of the hidden gems the show has produced in the modern era.

(One caveat: I’m not including any “Treehouse of Horror” episodes. The show’s annual Halloween anthology remains a treat, year after year, and pretty much all of them are worth watching. For now, let’s stick with canon…)

Season 9: Das Bus

A clever Lord of the Flies parody that blends the sharp characterizations of the early seasons with the surreal plotting of the late ’90s eps, “Das Bus” throws the series’ young characters into an unlikely situation and has a ton of fun with the results. The subplot (in which Homer tries to start an Internet business) has aged poorly, but the main story remains just as funny as ever – straight down to the closing narration from James Earl Jones.

Season 10: The Wizard of Evergreen Terrace

Homer, experiencing a midlife crisis, attempts to follow in the footsteps of Thomas Edison and become an inventor. A silly plot, but made worthwhile by funny jokes (many revolving around Homer’s ill-fated inventions) and a well-animated rendition of the Thomas Edison museum in New Jersey. Bonus points for the KITT cameo, back when that sort of stunt casting hadn’t yet grown stale.

Season 11: Behind the Laughter

One of the show’s weakest seasons ended on a high note, with a Behind the Music riff that poked fun at VH1 tropes and the show’s own longevity. A biting episode that played with the show’s format, and which could have easily served as a tongue-in-cheek series finale. (Good thing it wasn’t, or this would be a pretty short list.)

Season 12: Trilogy of Error

Fun with perspective, as we get to see the same day play out for Homer, Lisa, and Bart, in an episode that twists the three-act structure for the better. A definite thumbs-up. (So long as it’s not Homer’s thumb…)

Season 13: Half-Decent Proposal

Eleven years after “The Way We Was,” the show delivers a sequel even better than the original. The plot (in which Marge’s old boyfriend, Artie Ziff, returns in an attempt to woo her) serves to remind us why Marge and Homer are among TV’s most memorable couples, even as their romance is put to the test.

Season 14: I’m Spelling as Fast as I Can

Lisa episodes can be tricky, as they need to highlight the sincerity of her convictions without forsaking the jokes surrounding them. This episode, in which Lisa enters the national spelling bee (hosted by George Plimpton, shortly before his death) is a good template of how to do it right.

Season 15: The President Wore Pearls

One of the best Simpsons episodes of the modern era. A clever political satire and riff on Evita, this episode features rousing musical numbers and a surprisingly poignant climax. (Made more memorable by the hilarious delivery of Yeardley Smith: “At yahoo doooot com….”)

Season 16: A Star is Torn

Yeah, it was obviously designed to cash in on the American Idol craze, but it has a sweet father/daughter story at its core. Plus Homer delivering the most important lesson in the music business: “Don’t trust people in the music business.”

Season 17: The Seemingly Never-Ending Story

Non-Halloween anthology episodes were a staple of the show throughout the 2000s, with at least one episode per season being devoted to the format. Some episodes worked better than others, but none were quite as memorable as the ouroboros approach taken by “The Seemingly Never-Ending Story,” which packs in more layers of narrative complexity in 22 minutes than many cable dramas can do in 60.

Season 18: Springfield Up

Documentary-style episode, parodying the Up series. Not deep, but frequently hilarious, thanks in part to Eric Idle as the Michael Apted stand-in.

Season 19: Eternal Moonshine of the Simpson Mind

The best Simpsons episode of the 2000s, and one of the best episodes ever. A sweet, moving, and visually gorgeous look into Homer’s mind (inspired, no doubt, by the excellent and similarly-named Michael Gondry film) that gives the show’s ubiquitous lead his most sympathetic showcase in over a decade. A masterpiece of storytelling and animation.

Season 20: Gone Maggie Gone

“It’s really Maggie, Sherlock.”

Season 21: The Bob Next Door

Sideshow Bob episodes have grown more strained over the years, as the show tried to introduce new facets to his character (an Italian wife, devious parents). “The Bob Next Door” returns the series’ most memorable villain to form, and features a great climax at Five Corners. It isn’t “Cape Feare,” but what is?

Season 22: Angry Dad: The Movie

A funny sequel to Season 13’s “I Am Furious (Yellow),” featuring a fake Pixar short (“Condiments”) that’s one of the most inventive gags the show’s done in years. It’s quite a prophetic episode, too – not long after it aired, The Simpsons earned an Oscar nomination for Best Animated Short Film (“Maggie Simpson in The Longest Daycare”).

Season 23: Holidays of Future Passed

Perhaps the best Simpsons episode of the 2010s, this is a sweet and emotional “What if?” episode focused on an adult Bart and Lisa returning home for Christmastime. An underappreciated gem, no matter what time of year you watch it.

Season 24: The Day the Earth Stood Cool

One of the first episodes of the show to satirize millennial culture (in this case, a hipster couple that moves in from Portland). Silly and self-indulgent, but a lot of fun.

Season 25: Brick Like Me

Airing shortly after The Lego Movie hit theaters, this episode has a similar conceit, with Homer waking up in a Lego-infused world. A great story, with some impressive CG animation to ice the cake.

Season 26: Bart’s New Friend

Written by Judd Apatow in 1990(!), “Bart’s New Friend” boasts a simplistic concept (Homer gets hypnotized into believing he’s a ten-year-old), but it succeeds more than many other latter-day Homer/Bart episodes by swapping out cynicism for heart.

Season 27: Halloween of Horror

A Halloween episode that’s… canon? Yes, there’s a first time for everything. An excellent Homer/Lisa episode that examines childhood fears in a way that’s honest, clever, and even suspenseful. Proof that The Simpsons can succeed even when it breaks from decades-old formula.

Season 28: The Town

“The Simpsons travel to…” episodes are rarely among the show’s finest – too often they rely on exaggerated stereotypes rather than compelling stories. But “The Town,” which sees the family head to Boston, is the rare exception – a clever episode that riffs on the city while still featuring good material for
Homer and Bart. And the Dropkick Murphys number is a knockout.

Season 29: Homer is Where the Art Isn’t

By its twenty-ninth season, The Simpsons had parodied virtually every piece of pop-culture on the planet… so naturally, it was time to give Banacek a whirl. Featuring a clever mystery and a fun guest turn by Bill Hader (as “Manacek”), it’s a fine send-up to a forgotten TV drama.

Season 30: Bart vs. Itchy and Scratchy

Recalling Season 2’s classic “Itchy and Scratchy and Marge,” this episode skewers the concept of gender-swapped reboots, with controversy erupting when the show’s famed cat-and-mouse duo are reintroduced as females. The episode provides pointed commentary without taking a hard stance on the subject, recalling the best satires of the classic years. Like many of the other shows on this list, it can stand proudly alongside the episodes of the golden age.

Honorable Mentions

Most seasons from the modern era have more than one great episode. Here are ten more worth checking out:

“Miracle on Evergreen Terrace” (Season 9)

“HOMR” (Season 12)

“Brake My Wife, Please” (Season 14)

“Margical History Tour” (Season 15)

“24 Minutes” (Season 18)

“That ’90s Show” (Season 19)

“How I Wet Your Mother” (Season 23)

“Barthood” (Season 27)

“Kamp Kustier” (Season 28)

“Woo-Hoo Dunnit?” (Season 30)