This wasn’t the easiest list to make, but limiting myself to the better, earlier seasons does mean that I have less to choose from and therefore less crap to wade through. The primary common denominator amongst these 20 is that the stories they tell feel rote or boring. I can handle stupid but funny, wacky but fun, but certain characters and situations are simply comedic deadweight.

Just like my ‘best of classic era‘ list, I’m defining the classic era as seasons 3-8. There’s no real consensus but that’s where I choose to draw the line. I’m not including clip shows for obvious reasons – they’re just the worst (despite my fondness for ‘The 138th Episode Spectacular’)

20. Fear of Flying

Homer: Wait a minute…there’s something bothering me about this place. [looks around] I know! This lesbian bar doesn’t have a fire exit. Enjoy your death trap, ladies.

No episode with the above scene could ever be considered ‘bad’. But a trip into Marge’s backstory to uncover her fear of flying (something never mentioned before or after this episode) is less than successful at getting at the heart of what makes Marge, Marge. The ‘revelation’ that her father was a steward seems especially tame these days and the fact that it’s seen as the chink in her psyche that must be repressed is just bizarre.

19. Bart’s Girlfriend

Bart has exactly 2 girlfriends in the classic era (and seemingly 64 after season 8) but both of the episodes that introduce these characters are in my bottom 20 list. This episode comes off better because Jessica Lovejoy is actually quite a fascinating character; the reverend’s daughter who acts out because her parents are ignoring her desire to be her own, imperfect person. It gives her a nice dynamic with Bart and plays off his ‘badboy’ image which had grown tame over time.

18. Bart Gets An Elephant 

Bart: I wish had an elephant
Lisa: You did. His name was Stampy. You loved him.
Bart: Oh yeah

That quote was from season 9’s ‘The Two Mrs. Nahasapeemapetilons’. Now of course the joke is that all these crazy things keep happening to the Simpsons but so little of these actually resonate after the episodes end. But I’d like to think it alludes to how forgettable this story is. It’s not bad because of it’s wacky premise. It’s bad because it takes a wacky concept and tries to take it seriously. ‘What would life be like if a suburban family tried to keep an angry elephant in their backyard.’ Yeah it’d be expensive and unethical. But where’s my laffs? Where’s my laffs?

17. The Homer They Fall

This is actually quite an elegant and straight-forwardly told story about Homer’s meteoric rise through the ranks of local boxing leagues as the man who can’t be beat down. This episode has the feel of a movie, with neat cinematic techniques like the sepia tinged montage of Homer’s ascent through the boxing ranks used to quickly tell a loaded underdog tale that also need to include Moe’s heretofore unmentioned backstory. Having said that, there is very little room for laughs between all the montages, the plot necessities to introduce Homer’s condition and both Marge and Moe’s emotional arc. This leads to a rather boring, if well-told boxing yarn.

16. Bart the Fink

I was tossing up between either this episode or another Bart-solves-a-mystery-to-rectify-a-problem-he-initiated episode ‘The Day the Violence Died’ in this spot. But that episode’s truly bizarre final minutes give it a much need boost of absurdity. About as fascinating as an episode about Krusty’s tax fraud could possibly be, this episode tries to shake things up a bit with a 3rd act death twist, but the following mystery of what happened to Krusty is rote and unexciting as it’s not given time to fully develop.

15. My Sister, My Sitter

This episode is really quite painful to watch. It’s essentially a series of horrible things happening to Lisa. I suppose the cumulative effect of all this horror is meant to be seen as amusing, but the episode is too dark to find much humour in an unconscious boy falling down a steep hill as his sister is being questioned by the police. Season 9’s ‘Lost our Lisa’ does a slightly better job at depicting this type of story by rewarding Lisa in the end for all her efforts. This episode simply punishes her, but indicates that the punishment won’t really do her any long term damage. How fun?

14. Home Sweet Home Diddily-Dum-Doodly

This is similar to ‘My Sister, My Sitter’ is the sense that the first act is really just a bunch of horrible things happening that serve to discredit Marge and Homer as parents. At least in this case, the incidents are made somewhat amusing (Pets fornicating on the kitchen table?’). It’s the rest of the episode, once the children are in Flanders’ care that moves very slowly. There are some affecting moments such as the fake paper the children send their parents to show they miss them (‘Todd Smells? I already know that’) and the finale that reinforces Maggie’s bond with Marge. But there’s just something about half an episode of The Flander’s family’s goody two-shoes schtick that grows dull quickly for me.

13. Dog of Death

Episodes centred around Santa’s Little Helper don’t have a track-record of being particularly amusing. ‘Two Dozen and One Greyhounds’ at least brings the laffs and a memorable musical moment along with its usual ‘Bart doesn’t want anything to happen to his beloved pet’ type storyline. This episode focuses more on the family’s reaction to the dog in peril than the dog itself which is a shrewd move, but really it’s a small scale version of ‘Bart Gets An Elephant’, where showing the practicalities of paying for a dog’s surgery isn’t particularly funny.

12. New Kid on the Block

This is season 4’s sole entrant in this list and it’s the other ‘Bart gets a girlfriend’ episode. Again, this episode’s biggest problem is that it doesn’t bring the laffs. Now of course even a comedy shouldn’t be judged solely on its ability to elicit laughter. It’s telling a story and all good stories should be affective and engaging, no matter what genre. But this episode botches its ending by conveniently turning Moe into an actual psychopath and making the ending more about Jimbo and Moe’s interactions and less about Bart and Laura. The Homer-buffet subplot is fitfully amusing in parts and provides the first and possibly only mention of Captain McCallister’s name.

11. Homer Vs. Patty and Selma

Homer owes Patty and Selma money. Bart takes up ballet. Comedy gold, no? I enjoy the conclusion of this episode, but nothing that happens before is particularly inspired or exciting. It’s Homer hiding a secret from Marge and Bart hiding a secret from his school chums. It’s a little too repetitive and one-note.

Part 2 – Episodes 10-1