The Best and Worst Episodes of The Simpsons (S1-8)

This is the third such post of best and worst TV episodes lists I’ve done, the others being for The X-Files and Game of Thrones.  This time I am applying this ranking to The Simpsons.  However, it is important to note that this is not including the entire run of the longest running animated program.  Heck, that’s well over 600 episodes by now!  I don’t have THAT much free time.

Instead, I’ve decided to limit it to the first eight seasons of the series’s very-long run.  These are what I, and many other Simpsons fans, consider to be the golden years of the show.  During these years, The Simpsons was probably the best show on television.  Afterward, however, it really started going downhill and is so far removed from the quality of its past that its practically a different show now.  Season 9 still has some gems, but its pretty close to 50/50 for great vs. not so great episodes, so I just couldn’t include it.

So what I’ve done is rank all the episodes from these golden years, but what I am presenting here are the top ten and bottom ten for these eight seasons.  If you are interested in the full list, let me know, but otherwise see if you agree with these twenty choices, breaking down the best TV show ever.

The Top Ten Episodes

10. Treehouse of Horror V

Season 6

The Halloween episodes have become a staple of The Simpsons, telling three stand-alone stories usually touching upon well-known fiction.  The best of these came in season 6 in which The Simpsons did their brilliant send up of Kubrick’s The Shining, told a creepy tale of the school staff serving trouble-making kids in the cafeteria, and my favourite of the Halloween shorts, Homer creating a time-traveling toaster.

9. Who Shot Mr. Burns? Part 1

Season 6

Cliffhanger finales were not something The Simpsons ever bothered with…. except once.  This brilliant send-off of the infamous Dallas season finale managed to create an interesting mystery atmosphere in which many different motives for the titular crime were established.  From Burns’ ridiculous plot to block out the sun to Homer’s ridiculous obsession for Burns to know his name, this episode was chock full of great stuff.  Part 2 which followed it up was also great, but didn’t quite meet the same levels of quality.  The summer after this was quite fun, trying to follow the clues and figure out whodunnit.  Ah, good times.

8. The Way We Was

Season 2

The Simpsons has some great flashback episodes under their belt.  One of the show’s most touching moments came from the Maggie flashback episode where its revealed where her baby pictures are.  But the best flashback remains the first one they did, where the story of how Marge and Homer met is retold.  It speaks a lot to who those two characters are and the foundation of their relationship, which is the cornerstone of the entire series if you think about it.

7. You Only Move Twice

Season 8

One of the best one-shot characters The Simpsons ever gave us was Hank Scorpio, Homer’s short-time boss/global supervillain.  There’s some fun stuff going on here with James Bond spoofs, but told from the perspective of a really friendly bad guy.  This episode is pure funny from the moment Hank throws his shoes to when Homer gets the Denver Broncos as a gift.

6. Lisa’s Substitute

Season 2

Seasons 2 and 3 were really great at not only being funny, but having strong emotional cores behind their weekly stories.  The epitome of this was when Lisa made a connection with her substitute teacher Mr. Bergstrom, voiced brilliantly by Dustin Hoffman (back when guest stars actually gave performances and didn’t just speak blandly into the microphone).  This does a lot to explain the relationship between Lisa and Homer, as well as Lisa and herself.  Its an excellent half-hour of television.

5. Last Exit to Springfield

Season 4

“Dental Plan!”

Many have made an argument for this being the best  of all Simpsons episodes, and watching it again its easy to see why.  Its just great comedy from start to end with tons of iconic gags like the dental plan repetition, Homer needing to use the bathroom, and the Grinch parody at the end.  This is a textbook example of why The Simpsons at its peak is the greatest TV show ever.

4. A Streetcar Named Marge

Season 4

Their fourth season was probably The Simpsons at its height.  It had great episodes like Homer the Heretic, The Itchy and Scratchy Movie, the previous pick Last Exit to Springfield, one other big on still to come(…), and this one, where Marge takes part in a community theater production of A Streetcar Named Desire.   While Last Exit to Springfield was chalk full of brilliant comedic writing, Streetcar also has the personal story underlying it.  many episodes have dealt with the relationship of Homer and Marge, some are good, some are bad, and some are great.  This one is the best of them.

3. Homer at the Bat

Season 3

This is definitely more of a personal pick.  I have always had fond feelings for this episode for some reason.  There’s an ethereal feeling to the baseball/wonderbat stuff, but there’s also some damn funny gags involving the cast of ball players that join Mr. Burn’s softball team.  Steve Sax’s run in with the law is probably the best of these.  And of course there is that great song over the end credits.  Masterpiece.

2. Cape Feare

Season 5

Fans’ favourite returning character is of course the dastardly Sideshow Bob, who always has some crazy scheme to get revenge on Bart (who’s only 10 and already has two mortal enemies).  This is by far his best outing and indeed one of the best episodes ever, as almost any Simpson’s expert will agree.  Cape Feare goes beyond simple movie parody and really creates its own entity here.  This episode is chalk full of memorable lines (“Use a pen Sideshow Bob”), gags (Bart, wanna see my new chainsaw and hockey mask!”), and sketches (“Now remember, YOU are Homer Thompson).

And of course the rakes.  Ohhhhhh, the rakes.

1. Marge vs the Monorail

Season 4

I wasn’t really sure when I started ranking these which would end up on top.  There are so many great episodes, and honestly any of the top 5 there would have been excellent candidates for the #1 spot.  But I had to go with the Monorail episode.  This is just comedic gold all the way through.  Every joke lands jut the way it should, it has a great musical number, it has tons of memorable lines (“I call the big one Bitey”), it involves the whole town but still keeps the Simpsons family at the core, and has a great narrative arc which includes tension, relief, and connected plot points.  Its a great half-hour of television anyway you look at it.

Monorail has tons of iconic Simpsons “stuff” in it, like donuts, Homer having a wacky job, celebrity cameos (thank you Mr. Nimoy, even though you didn’t do anything), and a great silly ending.  Its so good.  Again, the best of The Simpsons really only differ by the tiniest of margins, but for this go around I am giving the crown to Marge vs. the Monorail.

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The Bottom Ten Episodes

Again, I remind you that these are the bottom episodes for the first eight seasons, otherwise none of them would be here as the last 20 or so years would encapsulate many, many worse episodes than these.  Its also worth noting that I did watch and rank all episodes in these seasons, and even ones that didn’t make the top 100 were still excellent episodes.  There is a LOT of quality here.  But every once in a while, even classic Simpsons had some episodes I wasn’t thrilled with.  Here they are.

10. Homer’s Night Out

Season 1

A lot of people like to get down on the first season of The Simpsons.  I understand why, even if I don’t entirely agree, as the animation is pretty crude and the characters and writers needed some time to find their groove.  But looking back on some, they are sort of just… meh.  And that’s what Homer’s Night Out it: meh.  It sees Homer become a notorious party animal because of a lewd picture taken with him dancing with a stripper at a bachelor party.  Its pretty tame.

9. The Old Man and the Lisa

Season 8

There are a few episodes on this bottom list that are reflective of the show’s later tendencies in the crappier seasons leaking out a bit.  This is certainly one of those.  It feels more like season 10 or after.  I just don’t care for it very much.

8. The Simpsons Spin-Off Showcase

Season 8

This was an interesting idea in theory, but in execution it really isn’t that great.  We get a 3-story structure similar to the Halloween episodes, but in each one this time we get a possible spin-off.  The best of the three is Chief Wiggam in New Orleans, but the Moe show and the variety show are really quite lame.  I mean, I know they are supposed to be, but its just too much.

7. The Simpsons 138th Episode Spectacular

Season 7

As awesome as the title for this episode is, its really just a clip show.  But at least it has Troy McClure introducing the segments.

6. Homerpalooza

Season 8

Some hallmarks of “bad” Simpsons includes trying desperately to capitalize on certain cultural touchstones and having soulless celebrity cameos, differing from the actual guest performances from earlier years that are there to play a character not to just show up for people to recognize them.  Homerpalooza is probably the origin point for these problems.  This is The Simpson’s trying to be hip-and-now, as it does so often these days, instead of creating classic TV comedy.  The cameos really feel like name dropping and checking celebrities off a list.  Its a sign of things to come.

5. Some Enchanted Evening

Season 1

While I actually like most of the first season episodes and don’t really agree with much of the criticism, I do confess that this episode sort of encapsulates or me what all those complaints are.  The animation is really quite bad, the story is beyond lame, that babysitter bandit is awful, and this just doesn’t work.  I don’t like it.

4. Burns baby Burns

Season 8

So this is the third Season 8 episode that is on here because it represents the problems that the later  years would have in abundance.  Burns Baby Burns really feels like it should come from one of the seasons in the teens.  It focuses entirely on a celebrity, makes up a lame plot contrivance like Mr. Burns having a secret child, and sees the beginnings of Homer’s decline as a character.  Homer here is getting into crazy schemes just because, something that he would become famous for later on.  In the good years, Homer gets into schemes for actual story reasons most of the time, and is usually a lot more subdued.  This is the beginning of “wacky” Homer, who frankly just isn’t as good.  And this is very obviously them writing an episode specifically for a celebrity guest star (Rodney Dangerfield in this case) and having them do their shtick, instead of formulating an episode with The Simpson’s and having cameos which make sense.  They made this work with Michael Jackson earlier on, but it really doesn’t work here.

3. So Its Come to This: A Simpsons Clip Show

Season 4

I mean, come on, its a clip show.  At least Bart shaking up the beer in the paint shaker was funny.

2. Another Simpsons Clip Show

Season 6

Same as above really.  The reason the first clip-show is above this one is that the framing device is a little more involved and interesting.

1.  Supercalifragilisticexpiali-d’oh-cious

Season 8

And so we come to the worst of the best.  The Simpson’s has always had a history with musical numbers, most of which are successful like “Who Needs the Kwiki-mart?” or “Monorail”.  But they just took it way too far with this Mary Poppins spoof.  There’s not much I like in this episode.  The story of Marge’s hair falling out is dumb, Sherry Bobbins is annoying and so is the singing.  So while the Simpsons has made over 150 great episodes in their first eight years, not all of them were gold unfortunately.

Still, when all is said and done, The Simpsons seasons 1 to 8, the only ones that really matter (though to be fair season 9 does have some gold), is very likely the best years of any television show I’ve seen.  While there may be some chinks in the armour, there really aren’t many, and they are far outweighed by many, many episodes that are pure comedic genius.  But not only was this the funniest show ever made, at its best it is also top-notch storytelling that defied television expectations.