Trivia: According to French Stewart during a 3rd Rock from the Sun reunion Q and A at the 2021 Vulture Festival, he and Joseph Gordon-Levitt could never get through the scene where Harry spits baby food at the baby without the two actors breaking character and laughing hysterically.
Fifteen Minutes of Dick - S2-E23
Trivia: At the book signing with Mark Hamill, a poster of the comic "Black Pearl" is displayed. Mark Hamill created and wrote "Black Pearl."
Trivia: Al Franken appears in this episode as a slimy politician. Franken would become a politician later in life, serving as a United States Senator for Minnesota. He ended up resigning in 2018 after photos surfaced of him on a USO tour pretending to grope the breasts of radio host Leeann Tweeden while she was asleep.
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