Sideshow Bob returns yet again in “Cape Feare” (S5, E2) and this time he wants to kill Bart. There’s a scene in which Bob repeatedly steps on rakes that smack him in the face that went on way too long. This was done to pad out the episode which was originally too short. It was hilarious to me that the scene went on so long when it first aired, but on a rewatch, this sort of thing is less funny.

There’s still a lot to like about this episode. Bob passing out because he writes all his letters in blood. The parole board letting Bob out of prison even though he tried to kill Selma because everyone in the courtroom (including her twin sister!) was also thinking about killing her. The Simpson family is placed into witness protection, but Homer repeatedly fails to respond to his new name of Mr. Thompson. Homer deciding to drive through a cactus patch, not knowing that Bob is strapped to the bottom of their car.

Bob is rude by smoking and laughing loudly at a movie theatre, but Homer outdoes his rudeness without even trying just by being himself. Bart tricks Sideshow Bob into singing an entire Gilbert and Sullivan opera instead of killing him. According to Wikipedia, this is the last episode produced by the show’s original writers, most of whom left after this. This might explain why The Simpsons largely change from being politically conservative to politically neutral at this time. (I don’t remember which episode it was, but there was one moment in an episode this season that poked fun at both Republicans and Democrats.)

US Presidents feature quite a bit this season. Richard Nixon vows revenge after Homer makes a pig sick in “Homer Goes to College” (S5, E3). (This episode also features the great moment of Homer singing “I am so smart. SMRT” while his house catches fire behind him.) Nixon and Reagan get into an exclusive event in “Rosebud” (S5, E4) while George H. W. Bush and Jimmy Carter are turned away for being one-term presidents. The first episode in which a Republican president is presented in a bad light would be “Treehouse of Horror IV” (S5, E5) in which Nixon, serving on the jury of the damned, calls Satan his master. I remember my mom being offended by this moment.

The Halloween Specials are always fun. This was the last episode written by Conan O’Brien since he left to do his own late night talk show at this time. His joke nickname in the credits is “Watch My Show” in reference to this. When Homer is too fat to fit down the hole leading to hell, Satan saying, “Your wide behind won’t save you this time” was a good line. Grandpa running into Bart’s room with a wooden stake saying “We have to kill the boy!” only to flee in terror when he learns that Bart is a vampire felt like a repeat of the zombie Flanders joke from a previous season. However, I liked when Bart and Lisa were exploring Burns’ mansion and discover a secret passage to his laundry. Also, when Bart is fleeing upstairs from vampires and sees a lever that turns the stairs into a super happy fun slide, it’s absolutely hilarious when he says, “I know I shouldn’t, but when am I going to be here again?” and pulls the lever. Great stuff.

Principal Skinner was a traumatized Vietnam War vet in the first four seasons. In season 5, he becomes a mama’s boy. He did refer to his mother before in a previous season, but he did so in an homage to Psycho. In the gremlin dismantling the school bus segment of “Treehouse of Horror IV”, he’s riding the school bus because his mother took his keys away. This is the first instance of the running gag of Skinner having an overly-controlling mother (or second, if you count the Psycho reference).

I’m finding a lot of episodes not to be as funny as I remember. I think this is partly due to how I’m watching them. Instead of waiting a week between each episode, watching them one after the other lessens their impact. The change in writing team is evident in the fifth season with a return to more situational-based comedy and less non sequiturs (although they’re still there.)

Some episodes are following a new format in which the episode starts out being about one thing, but part-way through, switches to something else. It’s like two shorter episodes have been mashed together. I think the first instance of this is “Bart’s Inner Child” (S5, E7) which starts out being about the injuries caused by Homer getting a trampoline, then pivots to making fun of a self-help guru who encourages everyone to do what they feel.

One of the funnier episodes this season is “Boy-Scoutz ‘n the Hood” (S5, E8) which starts out with Bart and Milhouse getting wasted on an all-syrup Squishee, and ends with Bart joining the Junior Campers and getting stranded in a raft with Homer and Flanders. In the opening, Homer is looking for a fallen peanut and instead finds twenty dollars. He at first says “D’oh” until his brain reminds him twenty dollars can buy many peanuts. Homer asks for further explanation and his brain tells him money can be exchanged for goods and services. My brothers and I loved this joke so much, we actually did a skit on our video camera recreating it.

I love the “Springfield, Springfield” song Bart and Milhouse sing during their wild night on the town, high on sugar. The knife safety manual which instructs Bart to “Don’t do what Donny Don’t does” is great. Dr. Hibbert removing a man’s appendix and tossing it like a grenade right before it explodes is amazing. It’s hilarious that Homer wastes water by washing his socks when their lives depend on rationing it. There’s too many great moments to list them all.

In “Homer the Vigilante” (S5, E11), Homer starts a vigilante group to stop a cat burglar, but instead his posse ends up committing more crimes. This episode has a couple good lines in it. While being interviewed on TV, the news anchor asks about the crime committed by the vigilantes and Homer says something like, “I’d be lying if I said my men didn’t commit any crimes” as if this is a denial. Later, Homer is passed out when the cat burglar steals the world’s largest cubic zirconia and the newspaper accuses him of sleeping on the job. He insists, “I wasn’t asleep! I was drunk!” To which Bart replies, “I believe you, dad.” Good stuff.

The Simpsons reach their 100th episode with “Sweet Seymour Skinner’s Baadasssss Song” (S5, E19) but don’t draw attention to the milestone other than what Bart writes on the chalkboard in the opening credits. In this episode, there’s a scene in which Bart’s dog is running through the vents of the school and Groundskeeper Willie needs to get greased up to catch the dog. My younger brother really loved it when Willie told the lunch lady, “Grease me up, woman!” I recall him quoting this line often.

I hate to say it, but overall, I think season 5 isn’t as funny as season 4. My favorite episodes on rewatch are “Cape Feare”, “Treehouse of Horror IV”, and “Boy-Scoutz ‘n the Hood”. I really liked a lot of the other season 5 episodes when they originally aired, but I don’t find them as funny anymore. Partly, this may be due to the fact that humor often depends on surprise, so an episode you’ve seen before won’t be as funny as the first time you watch it. Also, I’m less impressed with references to other TV shows, music, and movies. While making references to other shows can sometimes be delightful, over-reliance on references begins to feel lazy at a certain point.