Superintendent Chalmers becomes a teacher and gets Bart interested in learning about Teddy Roosevelt.
Tropes:
- A Day in the Limelight: For Superintendent Chalmers.
- Art Shift: The Couch Gag was done by John Kricfalusi in his own unique style.
- Continuity Nod: One of the items sold at the auction is a basket of Edna's Edibles muffins.
- Cool Teacher: Superintendent Chalmers of all people turns out to be this when he puts his hand to teaching, which he hasn't actually done in many years. He leads Bart and, eventually, the bullies and Milhouse with a more hands-on style that engages them in a way the classroom environment doesn't.
- The Dog Bites Back: The Roosevelt plot started with Principal Skinner standing up to Superintendent Chalmers.Chalmers: I'd say you're dumb as a post, but at least you can put a sign on a post that says, "Fresh strawberries-- one mile." You are a nitwit in an ill-fitting suit.
Skinner: (quietly) I'll have you know I'm lop-shouldered.
Chalmers: I'm sorry, what did you say?
Skinner: I said, I'm lop-shouldered...and I have been since I was hung by my armpits in a North Vietnamese prison!
Chalmers: I... I didn't know that.
Skinner: Oh, the list of things you don't know could fill a week's worth of morning announcements, with enough left over for a send-home flyer!
Chalmers: There's no need for hyperbole, Seymour.
Skinner: If you think it's so easy to handle Bart Simpson, why don't you do it yourself?!
(The rest of the teaching staff cheers.) - Dropped-in Speech Clip: Superintendent Chalmers plays a wax cylinder recording of a speech by Theodore Roosevelt (who actually receives a guest star credit).
- Seashell Bra: Mrs. Krabappel's mermaid costume.
- Silly Walk: According to John Kricfalusi's blog, one of the challenges he faced animating the Couch Gag was trying to keep Marge's iconic Beehive Hairdo from overtaking the visual of her crazy walk.
- Sixth Ranger: Kearney joins with Bart, Milhouse, Nelson, Dolph and Jimbo to help get Chalmers his job back, even though he did not partake in the field trip with the others.
- Special Guest: Teddy Roosevelt's actual voice is heard in the episode, through the playing of archived recordings; he is even listed in the episode's closing credits.
- Whole-Plot Reference: To Dead Poets Society and Taps.