The 15 Best Simpsons Episodes From The Modern Era
On October 1, The Simpsons will return for its thirty-fifth season. And the common refrain--that the show peaked, that it's 25 years past its prime--is itself getting a bit old.
The show will never be as consistently hilarious as it once was. But there are multiple episodes, scattered throughout the later seasons, that stand up to "classic" Simpsons quality. And there are enough of these hidden gems that an old-school Simpsons fan could spend a few weekends binging and catching up.
If you need a place to start, we've got you covered. Here are the 15 best Simpsons episodes from the past 15 seasons (Seasons 20-34), in chronological order. This gallery is for every lapsed Simpsons fan who watched the show during its golden age, stopped watching, and now wants to know what they missed. Which episodes would you take off the list, and which ones would you add? Let us know in the comments.
1. Homer and Lisa Exchange Cross Words (Season 20, Episode 6)
Lisa discovers a latent gift for crossword puzzles, and Homer finds a way to exploit that gift to make money. This is a spiritual successor to the classic episode "Lisa the Greek" (Season 3, Episode 14), where Lisa helps Homer bet on football games, and it explores the underrated dynamic between Lisa and Homer--a father who loves his daughter but doesn't quite know how to appreciate her.
2. The Squirt and the Whale (Season 21, Episode 19)
In this episode, Lisa tries to save a beached whale. It doesn't go well, of course. But the show does an incredible job of baiting us to make us think it just might. And the writers give us a heartfelt ending, where Homer rises to the occasion instead of Lisa lowering her expectations.
3. The Bob Next Door (Season 21, Episode 22)
The Simpsons get a new neighbor, and he seems simply perfect, except he has Sideshow Bob's voice. The best thing about this episode is the final reveal; you're just as confused as Bart is before you're given the full explanation. And even after the twist, the humor is sharp enough to hold your attention until the end.
4. Holidays of Future Passed (Season 23, Episode 9)
There have been multiple flash-forward episodes of the Simpsons, but this might be the best of them. Bart, Lisa, and Maggie, now all grown up, return home for the holidays and wrestle with the prospect of growing up and becoming parents. This episode was a possible series finale, if the contract negotiations with the voice actors didn't go as planned. Had it been, it would have done the series justice.
5. A Totally Fun Thing That Bart Will Never Do Again (Season 23, Episode 19)
Depressed with the repetitive boredom of his daily life, Bart tricks a cruise ship into thinking that a global pandemic has destroyed humanity, so that he and his family can live on the boat forever. It's a zany episode, but it knows when to rein itself in, and unlike many later Simpsons episodes, this one follows a single, strong plot thread all the way through.
6. The Day The Earth Stood Cool (Season 24, Episode 7)
Just in terms of density--the number of funny jokes told per minute--this episode falls right in line with classic Simpsons. It's a full-on roast of Portland hipsters, who overrun Springfield with compost piles, marijuana dispensaries, and farmer's markets. Again, the writers' focus--on a single plot line from front to finish--works wonders.
7. The Saga of Carl (Season 24, Episode 21)
Homer, Lenny, Carl, and Moe hit the lottery, but Carl absconds with the money, leaving the remaining three bar buddies to figure out what happened. Their investigation takes them to Iceland, where we learn more about Carl in a single episode than we've learned about him during the entire series. We're 35 seasons in, and The Simpsons can still find ways to surprise us.
8. Steal This Episode (Season 25, Episode 9)
Historically, some of the best episodes of The Simpsons have been when the writers lampoon Hollywood and its cynical triumph of money over artistry. And few episodes have brought this into focus better than this one, in which Homer is found guilty of copyright infringement, thanks to illegally showing Hollywood movies in his backyard. Of course, the ironies pile up; Homer sees his theft as a victimless crime, until he also has something to lose.
9. Brick Like Me (Season 25, Episode 20)
Usually, when Lego remixes an existing property (like Harry Potter or Star Wars), the resulting product is more family-friendly than the source material that inspired it. But "Brick Like Me" keeps the subversiveness of The Simpsons intact, which leads to some inspired brick-based humor. Half the fun is just watching the background and seeing which side characters and inside jokes you can spot.
10. Halloween of Horror (Season 27, Episode 4)
In Season 27, The Simpsons switched things up, and in addition to the annual Treehouse of Horror episode, the writers created an in-canon Halloween episode, in which three people break into the Simpsons home while Homer and Lisa are by themselves. The episode is funny, especially the side plot where Bart and Marge attempt to trick-or-treat. But it's also legitimately disconcerting, even when it's making self-aware jokes about itself.
11. A Father's Watch (Season 28, Episode 18)
Because he doesn't get validation from Homer, Bart seeks out validation in odd places. In this episode, Grandpa gives Bart a family heirloom instead of Homer, which tests the boundaries and the tenuous relationship between father and son. We also learn that Homer's bad parenting did not start with him. Prior to Homer, it was Grandpa, who learned it from his father, who learned it from his father. Old wounds run deep.
12. Woo-Hoo Dunnit? (Season 30, Episode 22)
Someone steals Lisa's college fund, and a TV crew arrives at the Simpsons residence to ask questions and investigate. It's a send-up of every true crime television show, with a deep-voiced narrator, dramatic editing, and constant suspicion of everyone, no matter how unlikely. At the very end, the writers reveal who stole the money, and it makes perfect sense, in a sad sort of way.
13. Sorry Not Sorry (Season 32, Episode 9)
In a building filled with burned-out educators, Ms. Hoover is the most jaded and cynical. And when she gives Lisa a lesser grade for running overtime on her presentation, Lisa yells at her teacher and then refuses to back down or apologize. Lisa is right about the message but not the delivery of that message. And that's a lesson that she has to learn the hard way.
14. Lisa's Belly (Season 33, Episode 5)
This episode takes on generational trauma and body shaming, all rolled into one when Marge calls Lisa "chunky." Lisa always makes it a point to take stands on important issues. But this particular incident felt more personal because it was coming from her mom instead of from society at large.
15. Treehouse of Horror XXXIII (Season 34, Episode 6)
The annual Halloween episodes are a highlight of every season. They're the one time each year that the writers can go completely wild, because everything that happens is non-canon. But out of all the recent "Treehouse" episodes, the Season 34 entry might have been the strongest. First is a parody of The Babadook. Then, we get a parody of Death Note, with the Simpsons reimagined as anime characters. And finally, we get a send-up of Westworld, in which Springfield is reimagined as a futuristic theme park where tourists can live out their favorite moments from the show. The highlight is when we see an entire room of host Lisas, covering every classic episode from prior seasons.