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The best episode of every season of 'The Simpsons'
Fox

The best episode of every season of 'The Simpsons'

“The Simpsons” has been on for over 30 seasons. That’s more than 680 episodes. It’s the quintessential cartoon and maybe the greatest TV show of all time. However, a lot of the attention goes to the first 10 seasons or so. Even huge fans of “The Simpsons” will talk trash about later seasons. We’re not here to do that, though. In fact we’re going to highlight the best episode of the first 31 seasons of the show. You may not like the later seasons, but there is still good stuff there.

 
1 of 33

“Life on the Fast Lane”

“Life on the Fast Lane”
Frinkiac

The first season of “The Simpsons” had some growing pains. The animation is a little crude, and the show moves a little slower. There aren’t really any great episodes in Season 1. However, “Life on the Fast Lane” shows the potential and promise of the show. It’s the episode where Marge meets a sweet-talking bowler named Jacques and almost has an affair.

 
2 of 33

“Dancin’ Homer”

“Dancin’ Homer”
Frinkiac

By Season 2, “The Simpsons” had found its footing. There are a few really good episodes, and it still feels like the classic version of the show. Homer gets a job as a mascot for the local baseball team as Dancin’ Homer until he gets the call up to Capital City, which has its own theme song sung by Tony Bennett.

 
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“Homer at the Bat”

“Homer at the Bat”
Frinkiac

This was the first season with a lot of episodes to try and pick from. Truly “The Simpsons” was amazing at its peak. The fifth-best episode of Season 3 could be the best episode of some shows. Weirdly, we’ve got two back-to-back baseball-related episodes. This one also features several cameos from actual baseball players, showing the reach the show had begun to have.

 
4 of 33

“Marge vs. the Monorail”

“Marge vs. the Monorail”
Frinkiac

When you think of the glory days of “The Simpsons,” this episode will likely be one of the first to come to mind. Who doesn’t remember when Lyle Lanley sold Springfield a shoddy monorail? The parody of “The Music Man” is loaded with great jokes and also one great song. Admit it. It’s in your head now.

 
5 of 33

“Homer Goes to College”

“Homer Goes to College”
Frinkiac

Conan O’Brien, the comedy legend, wrote only three full episodes of “The Simpsons.” One was “Marge vs. the Monorail.” Another was “Homer Goes to College.” Talk about a killer track record. No wonder he went on to such big things. You know what this episode is about based on the title, and that premise is great. The execution is somehow even better.

 
6 of 33

“Homie the Clown”

“Homie the Clown”
Frinkiac

In the very, very early days of “The Simpsons,” Matt Groening’s plan was to have Homer turn out to secretly be Krusty. They steered away from that, but in this episode Homer gets a chance to be a be Krusty’s stand-in. At first he hates it then starts to exploit it, and then the mob comes looking for Krusty and finds him. It’s a crazy ride and truly hilarious.

 
7 of 33

“Mother Simpson”

“Mother Simpson”
Fox

The seventh season of “The Simpsons” is great, but it’s a bit of a dip from the previous two seasons. It still has some great episodes though. “Mother Simpson” is fun, but it’s also emotional and heartfelt. After many years of never seeing his mom, Homer reconnects with her, only for her sadly to have to leave again.

 
8 of 33

“The Itchy & Scratchy & Poochie Show”

“The Itchy & Scratchy & Poochie Show”
Fox

And now we get to the best season of the show. This choice was so tricky. There are around a dozen episodes from the eighth season that are all-time classics. In the end, we’re going with “The Itchy and Scratchy and Poochie Show,” where a certain rockin’ dog was added to a classic cartoon.

 
9 of 33

“Realty Bites”

“Realty Bites”
Frinkiac

Homer is always getting new jobs. Marge has done it occasionally, but mostly she’s a homemaker and a mom. Here, she gets a job working for Lionel Hutz (who is always great to see) selling homes. That’s a ton of fun, but so is Homer’s adventures in owning a car that belonged to Snake, the noted criminal.

 
10 of 33

“When You Dish Upon a Star”

“When You Dish Upon a Star”
Frinkiac

Season 10 is where “The Simpsons” started to take a clear dip. There are episodes this season that are kind of mediocre for the first time since the show started. That being said, “When You Dish Upon a Star” is really good. It features top-notch celebrity cameos from Alec Baldwin, Kim Basinger and the best of the bunch, Ron Howard.

 
11 of 33

“The Mansion Family”

“The Mansion Family”
Frinkiac

This is a super goofy episode, which became more common around this point in the show’s run. Some of them are too ridiculous and don’t work. “The Mansion Family” does, though. Yes, there are pirates involved and also a monkey knife fight. Still, it’s a ton of fun.

 
12 of 33

“Skinner’s Sense of Snow”

“Skinner’s Sense of Snow”
Fox

The first episode of “The Simpsons” is a Christmas episode, and there have been a few good ones over the year. “Skinner’s Sense of Snow” isn’t the best of the bunch, but it is the best episode of the 12th season. The funniest bit is the Christmas movie Skinner makes the kids watch in school, especially the part where a stagehand accidentally walks into the screen.

 
13 of 33

“Poppa’s Got a Brand New Badge”

“Poppa’s Got a Brand New Badge”
Fox

The lead-up to the final episode of season 13 was lackluster, but “Poppa’s Got a Brand New Badge” knocks it out of the park. Homer has some history as a vigilante, but here he starts a legitimate security company. Of course in a city like Springfield, that can be sketchy, given the high level of crime. Indeed, Homer finds himself facing down Fat Tony and the mob. Things turn out fine, thanks to the dead eye shot of Maggie. Yes, the baby.

 
14 of 33

“The Bart of War”

“The Bart of War”
Frinkiac

Bart and Milhouse are good friends, but they end up on opposite sides of a battle here when Bart and the Pre-Teen Braves engage in a candy-selling war with the Calvary Kids, who feature Milhouse. This is perhaps the only episode of any cartoon to end with the singing of the Canadian national anthem.

 
15 of 33

“Simple Simpson”

“Simple Simpson”
Fox

In earlier seasons, “Simple Simpson” would stand out as being too silly. By this time, though, it didn’t make a blip. Some stuff, like a flying Dalai Lama, is too much. And yet there are a lot of great comedy beats to be found in Homer becoming a masked vigilant called Pie Man.

 
16 of 33

“All’s Fair in Oven War”

“All’s Fair in Oven War”
Fox

This is the best episode of the last 15 years or so of “The Simpsons.” No caveats needed. It’s a great episode, and it wouldn’t be out of place in the earlier seasons of the show. Marge’s foray into competitive baking is full of great jokes but also includes some genuine moments of emotion between Marge and Lisa. If you missed this one, check it out.

 
17 of 33

“The Last of the Red Hat Mamas”

“The Last of the Red Hat Mamas”
Fox

The early years of “The Simpsons” focused mostly on Homer and Bart. Other characters got a bit of short shrift, including Marge. Clearly, later seasons did better by the matriarch of the family, as she’s the focus of back-to-back season toppers. This time around she finally makes friends, only to find out they are planning to pull off a heist.

 
18 of 33

“The Haw-Hawed Couple”

“The Haw-Hawed Couple”
FOX

There were a few good episodes to pick from here, but we’re going with “The Haw-Hawed Couple.” Nelson is a bully, but unlike Jimbo, Kearney and Dolph, he has more depth to him. That allows the show to occasionally make him a main character in a story. Here, he becomes friends with Bart but he remains a bully, which makes things complicated for Bart. Along the way there are parodies of “Goodfellas” and “Brokeback Mountain.”

 
19 of 33

“Papa Don’t Leech”

“Papa Don’t Leech”
FOX

This episode rewards longtime viewers, as it brought back Lurleen Lumpkin, a character whose only primary appearance was way back in the third season. You know the country singer who falls in love with Homer? That’s a really good episode, and so is “Papa Don’t Leech,” its spiritual sequel. Maybe we will see Lurleen again down the road.

 
20 of 33

“How the Test Was Won”

“How the Test Was Won”
FOX

This is from the 20th season, which is more seasons than most shows will ever do. However, it’s also a pretty mediocre one. There is a handful of good episodes but no real standouts. Among the few solid showings, “How the Test Was Won” was able to win out. It’s mostly because of its final moments, which are just a dance party.

 
21 of 33

“Chief of Hearts”

“Chief of Hearts”
FOX

OK, Season 20 got pretty bleak, but Season 21 was a bit better. We have no caveats to provide for choosing “Chief of Hearts,” which is just simply a good episode. Homer and Chief Wiggum have a lot in common, including being dumb guys who love food. Finally, they become friends in this episode, though not without complications.

 
22 of 33

“Homer the Father”

“Homer the Father”
FOX

The premise of “Homer the Father” is strange but also kind of brilliant. Homer gets obsessed with watching cheesy ‘80s sitcoms, and he starts patterning his actions after the dads in those shows. For fans of pop culture, it’s a lot of fun to watch. The references and parodies make for a really funny episode.

 
23 of 33

“The Book Job”

“The Book Job”
FOX

You could make the argument that “The Book Job” is a great episode, which would make it the last great episode of “The Simpsons.” That doesn’t speak greatly of the 100-plus episodes that have aired since, but it remains impressive that the show has been on for this long. “The Book Job” is built like a heist movie, but it’s about writing a YA novel. That may not sound great, but it works and was a nice reward for everyone who has stuck around with the show.

 
24 of 33

“Hardly Kirk-ing”

“Hardly Kirk-ing”
FOX

Milhouse’s dad, Kirk, doesn’t have an enviable life, but he is an adult. That means he can do stuff that kids like Bart, Milhouse and Lisa can’t do. This is what gives the kids the idea to try and pass off Milhouse as his dad through some modifications. It works, but only so well. Still, it’s fun, and Kirk is always an enjoyable character in the right doses.

 
25 of 33

“The War of Art”

“The War of Art”
FOX

Speaking of Kirk, the Van Houtens are involved in this episode as well, which incluedes art, forgery and a trip to Puerto Rico. The travel doesn’t bring a ton of fun, but it gives the show some freshness. It’s an interestingly plotted episode as well.

 
26 of 33

“I Won’t Be Home For Christmas”

“I Won’t Be Home For Christmas”
FOX

Here’s another Christmas episode on the list. Having a holiday to build on probably helped a show that had been trying to generate stories, jokes and emotional beats for decades. There is a somberness to this episode, as Homer drifts through town late one night around Christmas. He even has a nice talk with Flanders. You know when Stupid Flanders and Homer are commiserating, things are strange.

 
27 of 33

“Halloween of Horror”

“Halloween of Horror”
FOX

For years the show has been doing Halloween episodes, but they have been the “Treehouse of Horror” specials. They are non-canonical and gory, spoofy stories. For the first time ever, the show did a Halloween episode that is actually canon, where we see the family celebrating Halloween. It was a totally unexpected treat, and fortunately the episode is quite good as well.

 
28 of 33

“A Father’s Watch”

“A Father’s Watch”
FOX

We aren’t going to sugarcoat it. The last three seasons of “The Simpsons” have been decent at best, with no episodes that really stand out. Are there good episodes? Sure, but nothing that rises above good. One of the good ones is “A Father’s Watch.” There’s some funny commentary in it about parenting and trying to balance rewarding your kids with having them have to work for things. By being pretty funny and not too silly, it ends up being the best episode of the 28th season.

 
29 of 33

“Homer is Where the Art Isn’t”

“Homer is Where the Art Isn’t”
FOX

Another art-related episode? Apparently it works for late-period “Simpsons.” You know what also works? A voice appearance by Bill Hader, who plays a parody of detectives from old cop shows in "Manacek." It doesn’t feel out of place, and frankly it made the show feel fresh. It may not have worked elsewhere, but Hader does a great job as Manacek.

 
30 of 33

“Woo-Hoo Dunnit?”

“Woo-Hoo Dunnit?”
FOX

And now we’ve reached a real milestone: the 30th season. This was the second-to-last episode of the season, and the 661st episode overall. To make it any good is honestly impressive, and this episode is good, as it is structured like an episode of “Dateline,” which works pretty well. The parody is clever, and there are some funny jokes to keep you entertained. Doing that after 30 years is incredible.

 
31 of 33

"Bobby, It's Cold Outside"

"Bobby, It's Cold Outside"
FOX

Surprisingly, this is the only Sideshow Bob episode to make this list. Maybe that's because there is less competition in the 31st season than during the glory days of "The Simpsons." Bob gets a job as a mall Santa while presents are disappearing around town. This is one of those Bob episodes where he's not the true villain, even if he is always villainous.

 
32 of 33

"The Dad-Feelings Limited"

"The Dad-Feelings Limited"
FOX

We never imagined getting this involved in the life of Comic Book Guy. We definitely never imagined it being worthwhile. Instead, "The Dad-Feelings Limited" is the best episode of season 32. The combination of Homer and Comic Book Guy is fun, and the episode also has a bit of a Wes Anderson homage in the mix, which works really well.

 
33 of 33

"Portrait of a Lackey on Fire"

"Portrait of a Lackey on Fire"
FOX

Waylon Smithers finally gets a serious boyfriend, though he ends up having more in common with Mr. Burns than originally anticipated. The 33rd season of "The Simpsons" was rife with "pretty decent" episodes, providing us with a high ceiling, but also a low floor. Among the many solid, unremarkable episodes, though, this story of Smithers' love life is the best.

Chris Morgan is a sports and pop culture writer and the author of the books The Comic Galaxy of Mystery Science Theater 3000 and The Ash Heap of History. You can follow him on Twitter @ChrisXMorgan.

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