Did Principal Skinner make a mistake when he offered his prized student a ride on a submarine. "Yellow Subterfuge" is the seventh episode of the show's 25th season.
Added:
A picture of Principal W. Seymour Skinner in all his glory saluting. Poor skinner is a vietnam vet and tries so hard to be a good man, but succumbs to the will of his mother and Bart Simpson.
Added:

The Simpsons Quotes

(Picking out a Tuxedo for Bart. He doesn't look pleased with his puffy shirt tuxedo.)
Bart: (frowning) Isn't this shirt kinda gay?
Clerk: Last time I checked, pirates weren't gay.
Homer: Eww, how'd you check?

Wow, now I see why they call you Miss Hoover. You must have been vacuuming for an hour.

Bart