The 20 Best Simpsons Episodes

What I believe to be are the 20 greatest episodes of longrunning animated series, The Simpsons. Episodes range in time from 1991 to 1997. I opted to pull no punches and went directly for what I consider to be the prime episodes of the show at its absolute peak. Many are those you might expect, but I did not refrain from included those which I feel deserve even if they, for one reason or another, aren't generally recognized as one of the best. Moreover, 20 is a small number when you have so many episodes to consider, so there are going to be plenty of great episodes I haven't included. Without further rambling, here's the list...
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1.
The Simpsons (1989 TV Series)
Episode: Summer of 4'2" (1996)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
After realizing how unpopular she is at school, a disillusioned Lisa sees the vacation to Ned Flanders' beach house that the family has planned as an opportunity to reinvent herself and make some friends. (22 mins.)
“ Season 7
Showrunners: Oakley & Weinstein

The epitome of the Simpsons at its best, with hysterical situational humour, inviting storytelling, and a great big heart. Evokes feelings of nostalgia even if you haven't even personally experienced those innocent summer days. ” - nauru-1
 
2.
The Simpsons (1989 TV Series)
Episode: And Maggie Makes Three (1995)
    1 2 3 4 5 6 7 8 9 10 8.6/10 X  
Homer recounts the story of Maggie's birth when the kids ask why there are no photos of her in the family album. (22 mins.)
“ Season 6
Showrunner: Mirkin

As far as I'm concerned, the flashbacks about the Simpsons roots are the backbone of the Simpsons characters. This one is standout with the bittersweet tale of the sacrifices one may have to make when another child comes along. Manages to be both hilarious and touching at the same time. And who can forget that sweet ending? ” - nauru-1
 
3.
The Simpsons (1989 TV Series)
Episode: Last Exit to Springfield (1993)
    1 2 3 4 5 6 7 8 9 10 9.0/10 X  
Homer becomes union leader and leads a company strike when Mr. Burns takes away the company dental plan. (22 mins.)
“ Season 4
Showrunners: Jean & Reiss

Okay, so it's almost gotten to the point where it's cliche to include this one on here, but there's a reason it gained so much popularity in the first place. It's perhaps the best foundational example of the Simpsons' quick-paced, absurd, and witty sense of humour. Essentially every gag and humourous exchange, and there are a ton in this one, are insanely memorable and for good reason. Bizarre, entertaining, and hilarious. ” - nauru-1
 
4.
The Simpsons (1989 TV Series)
Episode: Marge vs. the Monorail (1993)
    1 2 3 4 5 6 7 8 9 10 9.0/10 X  
After receiving a considerable donation of money, the people of Springfield decide what to spend it on... (22 mins.)
“ Season 4
Showrunners: Jean & Reiss

If Last Exit ever had a partner-in-crime, it would in all likelihood be Marge vs. the Monorail. In its historical context, this episode went really out there. But now when you consider that Homer went into outer space the next year, not quite so much. What really sells this episode, though, is its humour. In terms of pure comedy, for even the dramatic story is riddled with a good-natured silliness, this is one of the best. A particular joke with the one-off doctor might just be my favourite of the series, too. ” - nauru-1
 
5.
The Simpsons (1989 TV Series)
Episode: Homer at the Bat (1992)
    1 2 3 4 5 6 7 8 9 10 8.7/10 X  
Homer and his co-workers qualify for the plant softball team's league final, but Mr. Burns hires nine professional MLB players in order to win a $1 million bet. (22 mins.)
“ Season 3
Showrunners: Jean & Reiss

I have to be honest here: I don't even care much for baseball. What's more, a large cast of professional athletes playing a prominent role in the story sounds like a problem. However, at this point in time, it seems they could do no wrong. This episode is exceptionally funny and effortlessly puts a slew of guest stars to actual use. I don't know what's so funny about Major League Baseball players all facing an ill-fated occurrence, but every time I see it never ceases to entertain. ” - nauru-1
 
6.
The Simpsons (1989 TV Series)
Episode: Lisa's First Word (1992)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
While trying to coax Maggie into saying her first word, Homer and Marge talk about how Lisa spoke hers. (22 mins.)
“ Season 4
Showrunners: Jean & Reiss

The second inclusion of the Simpsons flashback stories, and yet another one that explores the family's past with great sincerity. The highlight to see probably has to be seeing a very little Bart who is so expertly portrayed at having to deal with a new addition to the family. To top it off, you've got maybe my favourite moments of the series with the ending that never fails to invoke a tear. ” - nauru-1
 
7.
The Simpsons (1989 TV Series)
Episode: Itchy & Scratchy Land (1994)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
A family vacation to Itchy & Scratchy Land turns disastrous when the robots malfunction and turn on the tourists. (22 mins.)
“ Season 6
Showrunner: Mirkin

Another episode that works primarily on humour. The family going to a theme park sounds simple enough and it's a premise that has beaten to death over time. However, this is the quintessential vacation episode. They're not going to some exotic place or meeting up with an assortment of half-baked stereotypes. It's just the family faced with the perils of a bustling tourist destination. And that's not even getting into the brilliant satire on Disney in particular. ” - nauru-1
 
8.
The Simpsons (1989 TV Series)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Milhouse falls in love with Samantha, a new transfer student, and Bart becomes jealous of all the time they are spending together. Meanwhile, Homer orders a subliminal weight loss tape, but is given a vocabulary builder by mistake. (22 mins.)
“ Season 3
Showrunners: Jean & Reiss

Alright, I know this one won't be on everyone's list, but I don't see why not. Admittedly, it's not the easiest to identify why it's a great episode. What you get is a diverse variety of subtle and standout humour consistently, but what I think pulls it off, much like Summer of 4 Ft. 2, is you've got a particular interesting dynamic going on between the characters. Samantha Stanky appears in her first and only speaking appearance and is actually kind of complex. And, hey, if all else fails, think about the golden Troy McClure sexual education video. ” - nauru-1
 
9.
The Simpsons (1989 TV Series)
Episode: Homer Goes to College (1993)
    1 2 3 4 5 6 7 8 9 10 8.6/10 X  
When a surprise inspection of the nuclear power plant reveals that Homer is not qualified to do his job, he is forced to go to college. (22 mins.)
“ Season 5
Showrunner: Mirkin

Alright, it took long enough to include a season 5 episode, but here we are. I know some people having mixed feelings about as Homer is quite clearly off in his own little world in this one. He doesn't really have the balance that you might normally get out of him at this point in the series. I think it works here, particularly he's because so naive and good-natured. The title says all you need to know about the plot going in, but what sells it is Homer's very misguided view about college life. He's expecting what he sees in movies and is completely ignorant to the more tranquil environment surrounding him. Couple this with exceptional comedy and you've got a great gagfest. ” - nauru-1
 
10.
The Simpsons (1989 TV Series)
    1 2 3 4 5 6 7 8 9 10 9.1/10 X  
After Mr. Burns steals oil from Springfield Elementary, an unknown person, seemingly in retaliation, shoots him. (22 mins.)
“ Season 6
Showrunner: Mirkin

Admittedly, it was quite tough to separate the first and second Who Shot Mr. Burns?, but feel free to view them as one entity if you like. I chose the first one because the buildup and closing mystery is both unique to the series and perfectly executed. The time and care taken into this season 6 close does not go unnoticed. Not only is it into for those sleuths out there, but it's one of the best usages of the characters around Springfield all involved in a single story. Perhaps the only time we'll ever get a taste of a cliffhanger on the Simpsons. ” - nauru-1
 
11.
The Simpsons (1989 TV Series)
Episode: Duffless (1993)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
After Homer is arrested for DUI, and loses his driver's license, he is put to the ultimate test when Marge pressures him to give up beer for a month. (22 mins.)
 
12.
The Simpsons (1989 TV Series)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
Marge and Homer lose custody of the kids, who are sent to live at the Flanders' house. (22 mins.)
 
13.
The Simpsons (1989 TV Series)
Episode: Treehouse of Horror V (1994)
    1 2 3 4 5 6 7 8 9 10 9.1/10 X  
The family's job at Mr. Burns' country estate goes awry when Homer goes mad. Meanwhile, Homer's attempt... (22 mins.)
 
14.
The Simpsons (1989 TV Series)
Episode: Lisa's Substitute (1991)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
Lisa has a crush on her substitute teacher, who seemingly represents everything that Homer is not. Meanwhile, Bart decides to run for class president, and becomes the overwhelming favorite. (22 mins.)
 
15.
The Simpsons (1989 TV Series)
Episode: Colonel Homer (1992)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
Homer becomes the manager of a beautiful young country singer and finds himself almost attracted to her, sparking Marge's jealousy. (22 mins.)
 
16.
The Simpsons (1989 TV Series)
    1 2 3 4 5 6 7 8 9 10 8.8/10 X  
After Bart inadvertently becomes drunk at a St. Patrick's Day celebration, an old prohibition law banning drinking in Springfield is rediscovered and enforced. Desperate to keep alcohol in the city, Homer takes matters into his own hands. (22 mins.)
 
17.
The Simpsons (1989 TV Series)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
Mrs. Krabappel, tells Marge and Homer about the things Bart has been doing, and Homer decides to punish him.; Bart is unable to see Itchy & Scratchy movie. (22 mins.)
 
18.
The Simpsons (1989 TV Series)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
Homer's marriage is in trouble when he develops an attraction to a new co-worker. (22 mins.)
 
19.
The Simpsons (1989 TV Series)
Episode: Lisa's Sax (1997)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
Homer recounts the story of Bart's first day of school, which corresponds with the story of how Lisa got her saxophone. (22 mins.)
 
20.
The Simpsons (1989 TV Series)
Episode: Bart the Lover (1992)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
After Mrs. Krabappel gives Bart a month of detention, he gets his revenge by responding to her newspaper singles ad. Meanwhile, Marge suggests Homer to start a swear jar to stop him cursing. (22 mins.)