In this episode written by Tim Long, Superintendent Chalmers becomes a teacher and gets Bart interested in learning about Teddy Roosevelt.
- A Day in the Limelight: For Superintendent Chalmers
- Art Shift: The Couch Gag was done by John Kricfalusi in his own unique style.
- The Dog Bites Back/Lets See YOU Do Better: 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: 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.)
- Seashell Bra: Mrs. Krabappel's mermaid costume.
- 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.
- Took A Level In Jerk Ass: Lisa has done this by planning to rat on Bart to Marge about his stunt.
- Whole Plot Reference: To Dead Poets Society.