Superintendent Chalmers becomes a teacher and gets Bart interested in learning about Teddy Roosevelt.

!! Tropes:
* ADayInTheLimelight: For Superintendent Chalmers
* ArtShift: The CouchGag was done by Creator/JohnKricfalusi in his own [[DerangedAnimation unique style]].
* TheDogBitesBack[=/=]LetsSeeYOUDoBetter: The Roosevelt plot started with Principal Skinner standing up to Superintendent Chalmers.
-->'''Chalmers''': [[InsultToRocks 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...[[RageBreakingPoint and I have been since I was hung by my armpits in a North Vietnamese prison!]]
-->'''Chalmers''': [[OhCrap I... I didn't know that]].
-->'''Skinner''': [[TheReasonYouSuckSpeech 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.)''
* SpecialGuest: 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.
* TookALevelInJerkAss: Lisa has done this by planning to rat on Bart to Marge about his stunt.