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.
Other mistake: When Harry spits baby food on the baby (the camera lens in actuality) in retaliation for the baby spitting food on him and Tommy, Joseph Gordon-Levitt breaks character and laughs uncontrollably and looks at and gestures to off-screen crew members a couple times. (00:06:25)
Trivia: Dick is never seen walking in this episode and is only in an upright position when he moves from the chair in the lounge room to the wheelchair in the opening scene. This is because John Lithgow hurt his ankle playing tennis, and the episode was written to allow him to be in a wheelchair for the entire episode.
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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