The Big Giant Head Returns Again (1) - S5-E21
Dick: Hey Tommy, how was school?
Tommy: Terrible. I got hauled into the principal's office because of my grades.
Harry: What'd he do to ya?
Tommy: Made me Valedictorian. Apparently I have the best grades in the school, dammit.
Dick: But you barely ever go to class.
Tommy: I know. That's how stupid everyone else is. Dammit!
Other mistake: Sally mentions that she makes jello with cheese, but many times the aliens have shown that they are terrified of Jello.
Tricky Dick - S3-E3
Trivia: Dick's rant about his perceived evils of rock music is identical to Reverend Moore's (also played by John Lithgow) opposition to dancing from the film "Footloose."
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Answer: The writers often have Dick respond to Mary with a retort that he thinks is in the common vernacular but makes a mistake in wording that is often funny. Dick seems to be imputing a criticism from Mary and responds with a corruption of the more common "I'm going to wear your ass like a hat!" I doubt it has anything to do with owing taxes. Probably just one of the writers assuming a common regional phrase would be universally recognized.
That makes total sense. I always interpreted it as perhaps snowshoes are an expensive item, and given that he was blaming Mary for his newfound financial woes, he was equating her living off his generosity and used snowshoeing as a metaphor.
Phaneron