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I just ran the first version of the prompt on Opus 5.5 medium:
Thought for 6s
Trying to place a half-remembered meme name.
Checking whether Principal Skinner matches the half-remembered name.
“Big Butt Skinner” is a gag from The Simpsons, specifically the Season 6 episode “Bart’s Comet” (1995).
At the start of the episode, Principal Skinner is about to launch a weather balloon in front of the school. Bart has secretly swapped in his own balloon, which carries a crude drawing of Skinner with an enormous rear end and the caption “Hi! I’m Big Butt Skinner.” It floats over Springfield to the whole school’s delight and Skinner’s humiliation.
Why it matters:
Plot catalyst. As punishment, Skinner makes Bart help him with his amateur astronomy before dawn. While looking through the telescope, Bart spots a comet, which gets named after him and turns out to be on course to hit Springfield. That leads to the episode’s main plot: town-wide panic, a failed missile interception, Ned Flanders’s overcrowded bomb shelter, and the comet finally burning up in Springfield’s thick layer of air pollution, shrinking to a pebble.
Character dynamics. The prank captures the Bart–Skinner rivalry well. Skinner wants to be a serious man of science and leave his mark (he hopes to discover a comet himself), and Bart’s lowbrow vandalism ends up getting him the glory instead.
Cultural afterlife. The phrase became one of the show’s widely quoted lines from its golden-age era (roughly Seasons 3–8), and it survives in memes and fan references.
I’m confident about the episode and the basic setup. Some smaller details, such as the exact wording of the caption, could be slightly off from memory.
Retrying four time got one "I don't know and I'd rather not guess" type answer and three essentially the same as the above. Technically it identifies "Big Butt Skinner" as the joke itself rather than the balloon, but this seems like a pass to me.