Portrait of Tommy as an Old Man - S3-E19
Harry: Hey, what's the matter, Tommy?
Tommy: I have to write a twenty-page history paper by tomorrow.
Harry: Oh, that's tough.
Tommy: Oh, oh, and on top of that, George Kapasouris was waiting for me after school to beat me up 'cause I wouldn't let him cheat off my algebra test.
Harry: Whoa, so what'd you do, hop the fence and run home?
Tommy: Well no, I kicked his ass, but I mean, that's not the point. I shouldn't have to do that.
Don: Ass right there, freeze-hole!
Just Your Average Dick (1) - S3-E22
Mary: Dick, you and your family, I know you mean well but sometimes it's like being around the Addams family.
Dick: Well, I will admit that John Adams' views of a strong central government may have been ahead of their time, but I...
Mary: That's not who I meant.
Dick: John Quincy Adams? You're comparing me to that freak show!?
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