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Because the whole joke with Homer is that he’s fat, more so than the average American. The average American has gotten fatter. So Homer had to as well to make the joke work.
I don’t know what year he was 260lbs, but if that joke were made today, it would say 350lbs.
Homers night out, season 1, 239lbs.
Brush with greatness, season 2, he dropped from 260 back to 239lbs.
He evolves to partially match the norms of the time
