“Don’t worry, Mom. I’ll bust you out of there just as soon as I get a cocktail dress and a crowbar.” – Bart Simpson
“Bartina, until I met you, I was the loneliest warden in the penal system.” – Imaginary Warden”
“Fresh.” – Bartina
“Oh, down I go.” – Imaginary Warden
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(The crotch really does wear out too fast.)
Dead Homer Society 
i’ve always been curious as to what the writers were thinking when they wrote this – was it to be disturbing? absurd? were they trying to insinuate that Bart had a thing for X-dressing?
Personally I think they were trying to cover the absurd angle, similar to a Monty Python skit.
While scene like this in today’s comedy would imply that the character has a less-than-vanilla-like curious side to him, back then it was just to be silly.
The same thing happened with Family Guy – first Stewie’s coulple-like relationship with Rupert and even Brian was silly but innocent, because his bear and his dog were all he knew, then it started to get a little more outrageous, as the writers tried to (unsuccessfully) push the envelope.
ANother Bart X-dressing scene was from a ZS episode where he “gets into the cheerleading equipment”. It was also silly and disturbing, but it didn’t work as well as this scene, probably because it tried too hard, and we were sick of Bart’s antics.
Yeah I think that was from a Season 11 episode. Homer commented on Bart “coming out of the pep closet”.
“Brothers Little Helper”. Seems like they just put that cheerleading joke in for that cheap punchline.
I am pretty sure this is mainly for absurdity. I am also pretty sure that you are overthinking this just a little bit, maybe.
probably
I love this scene lol and guys if anyone is reading this I just saw again a Simpsons episode where Ned Flanders takes in two college age females (in college no less!) and Homer ends up infuriating Ned by not telling him that they were having sexy slumber party’s/pillow fighting in his house and putting it on the web, Ned ends up moving to a very right wing town and Homer ends up with a bigger jerk then even him living next store. I like this episdoe and for some reason consider it Homer’s apology to Ned for being a jerk and also only semi ZS.