The 10 Best Episodes of The Simpsons

The Simpsons has been airing new episodes for over 30 years. While it is not the phenomenon it once was, it holds a place within the highest echelon of pop culture. Due to a drop in the show’s quality over the years, many forget that its first few seasons not only changed television forever, but altered our cultural landscape. The Simpsons reflected the realities of the American family. And this was during a time when reality was considered taboo. Below is our list of the best episodes of The Simpsons

10. Lisa’s Substitute (Season 2)

A retro still from the simpsons

Something of an anomaly amidst the other episodes on this list, the charm of “Lisa’s Substitute” lies more in its emotional impact than its hilarity. This is not to say that the episode doesn’t have its share of comedic moments (i.e. the brilliant political satire that is Bart’s run for class president). But it is mostly an earnest exploration of Lisa’s character. It expounds upon the struggle that comes with being the smartest member of a family full of–to put it bluntly–dimwits.

It must be noted that, while celebrity cameos in The Simpsons are a hit-or-miss, Dustin Hoffman’s performance as the titular character is especially moving. Many viewers are even brought to tears by the final goodbye between Lisa and Mr. Bergstrom.

9. Homer the Heretic (Season 4)

With an episode like “Homer the Heretic,” it’s easy to see why The Simpsons garnered so much controversy during its early years. (Even President George H.W. Bush was bashing the show for its supposedly negative portrayal of the American family.) This episode details Homer’s journey away from organized religion, which initially stems from his being too lazy to go to church. “I’m not a bad guy. I work hard, and I love my kids,” Homer proclaims. “So why should I spend half my Sunday hearing about how I’m going to Hell?” Such hilarious yet philosophical questions are littered throughout the episode. “Homer the Heretic” challenges the merits of faith-based family structures without venturing into cruelty.

8. The Itchy and Scratchy Movie (Season 4)

a publicity still from the simpsons

A fast-paced and gag-filled episode, “The Itchy and Scratchy Movie” tells the story of Homer’s shallow attempt to finally discipline Bart. After neglecting to watch Maggie, Bart is told by his father that he can never watch the newly released Itchy and Scratchy Movie. Does this punishment work to straighten Bart out?

Apparently, it does. The final scene fast forwards 40 years. Bart has become a chief justice of the Supreme Court, and soylent green has become a staple food. “The Itchy and Scratchy Movie” isn’t the series’ most touching moment, but it is one of the funniest. 

7. Mr. Plow (Season 4)

“Mr. Plow” is a cultural phenomenon in and of itself. From the still-catchy-after-30-years Mr. Plow theme song to a cameo from a seemingly delusional Adam West, this episode has everything that a fan of the series could want. Plus, it delves into the backstory of my personal favorite Simpsons character Barney Gumble. Via a flashback sequence, we find out that Barney was a successful academic before Homer ruined his life by giving him his first beer. 

6. Duffless (Season 4)

homer simpson and marge simpson dancing
Source: Moviestillsdb

“Duffless” is a perfect example of the show’s ability to remain whimsical in its addressing of serious issues. In the case of this episode, the serious issue is Homer’s alcoholism. After Homer receives a DUI, Marge asks him to refrain from drinking for a month. His struggles with sobriety reflect the extent of his drinking problem, which the series often plays off as a joke. The episode ends on a romantic note, with Homer and Marge biking into the sunset. After a month of sobriety, Homer realizes that true happiness is found in family, not in alcohol.

5. Lisa vs. Malibu Stacy (Season 5)

This episode proves that—despite the controversy that surrounded it—The Simpsons did carry a positive message. When Lisa buys the new “talking Malibu Stacy” doll, she is shocked to find that all the toy says is a series of sexist self-depreciations. (i.e. “Don’t ask me. I’m just a girl.”) What follows is an ideological battle between Lisa and the manufacturers of Malibu Stacy. “Lisa vs. Malibu Stacy” addressed misogyny ingrained within popular culture long before doing so was the norm. 

4. Homer the Great (Season 6)

the simpsons fighting over donuts

“Homer the Great” finds Homer thrust into a leadership position of the Stonecutters, an obvious satirization of elite secret societies like the Freemasons. The Stonecutters claim to “control the British crown” and “keep the metric system down.” Realistically, however, they pretty much just drink. The episode is less a comment on secret societies specifically, and more a general mockery of those who unjustifiably hold power.

3. 22 Short Films About Springfield (Season 7)

One of the best aspects of The Simpsons is its abundance of side characters. “22 Short Films About Springfield” explores the lives of these side characters. From Bumblebee Man to Cleetus the Slack-Jawed Yokel, all our favorite under-appreciated characters are present. Also featured in this episode is the famous, now heavily memed “steamed hams” joke.

2. A Milhouse Divided (Season 8)

a publicity still of milhouse van houten

Some fans argue that season 8 marked the beginning of the end for The Simpsons: that episodes like “You Only Move Twice” and “The Homer They Fall” found America’s favorite family in situations a bit too ridiculous, a bit too cartoonish. However, even these fans would have to admit that “A Milhouse Divided” is one of the series’ finest moments. Like “Duffless,” the episode touches upon a very serious issue–in this case, divorce–in a whimsical way. One cannot help but simultaneously laugh at and feel bad for Kirk Van Houten as he attempts to launch his post-divorce singing career. Surprisingly, the Van Houtens do not get back together in the end.

1. Homer’s Enemy (Season 8)

Here’s another controversial episode. If “Homer’s Enemy” is guilty of anything, it’s that it’s maybe a bit too grounded in realism. You could even see it as a satirization of the series itself. Critics don’t often list it as one of the best episodes of The Simpsons, which is a shame. We believe that it is the single best episode.

The episode sees Homer get a new coworker, Frank Grimes, at the power plant. Grimes has struggled throughout his life. Unlike Homer, he has a degree in nuclear physics and takes his job very seriously (as he should). Homer’s ignorance and carefree nature disgusts Grimes. Their feud results in one of the darkest endings ever seen on The Simpsons.

What are, in your opinion, the best episodes of The Simpsons? Did we leave out any classics? Let us know in the comments below!

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