A Nightmare on Dick Street (1) - S2-E25
Continuity mistake: In 1-2: "Post Nasal Dick", Harry has a dream about Martha Stewart. But in this episode they panic because they dream and have nightmares and don't know what they are. Shouldn't Harry have panicked when he dreamed about Martha Stewart?
Dick and the Single Girl - S2-E24
Continuity mistake: When Sonja takes Dick's belt, she has it in her right hand, away from Dick. In the next few shots, Sonja no longer has the belt, but it is back around Dick's pants. Yet the next shot (at the door), it's in Dick's hand. (00:16:30)
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