Unless the show broadcasts something unspeakably, morally wrong, The Simpsons is and always will be one of the greatest comedies ever to grace the small screen. The golden years of the show remain some of the funniest TV there has ever been, and even the older episodes can be a pleasant surprise from time to time.
More to the point, the sheer longevity of the show is something to behold. But let’s not kid ourselves: The Simpsons has jumped the shark, time and time again.
This isn’t a controversial opinion, and it’s said with love. When you set such high standards for yourself, eventually you’re going to be unable to meet them.
When precisely The Simpsons first jumped the shark is a matter for heated debate, but let’s not beat around the bush: this isn’t an isolated event. Whether this was due to outside influences or the show’s decreasing writing standards, an internal or external issue, or even good episodes opening the door for bad, The Simpsons has had more than its share of regrettable moments.
The good still outweighs the bad by a huge margin - but the show’s follies are adding up.
10. Frank Grimes
Let’s note first of all that season eight episode “Homer’s Enemy” is classic Simpsons. It’s laden with jokes, has one of the all time great one-off characters in Frank Grimes, and perhaps the finest Simpsons b-plot (Bart owning a factory), give or take Homer’s time as a sugar baron.
Unfortunately, the episode also gave birth to a character fans of the show refer to as “Jerk-Ass Homer”. While the Simpson patriarch began life as a well meaning, if idiotic and often destructive figure, “Homer’s Enemy” begins the character’s transition to an openly selfish and often unpleasant person.
He’s boorish at worst in the episode itself, but the ending - falling asleep at Grimes’ funeral to gales of laughter from friends and family - can be seen as the moment the writers realised they could mine easy laughs from having Homer turn into an often downright nasty piece of work.
It’s one of the most common criticisms of later Simpsons - the writers even showed their awareness of it by having the character smoke “Jerk-Ass Homer Cigars” after an act of villainy. The episode itself is superb, but it set an unpleasant tone to follow.