Revealing mistake: Near the end when Randy is driving away with Harry you can see that the steering wheel doesn't move when Randy turns it.
36! 24! 36! Dick! (1) - S3-E14
Revealing mistake: The mandolin that Dick is playing has no strings. (00:15:40)
Revealing mistake: When Harry throws the tent against the ground, his left foot bumps against the large rock on the ground and the rock moves. (00:07:20)
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)
Dick's Big Giant Headache (1) - S4-E23
Trivia: When the Solomons meet the Big Giant Head at the airport and ask how his flight was, he says that it was horrible because when he looked out the airplane window, he saw something on the wing of the plane. Dick responds that the same thing happened to him. William Shatner appeared in the 1960's Twilight Zone episode "Nightmare at 20,000 Feet" in which a gremlin tried to destroy the wing of a plane. John Lithgow appeared in "Twilight Zone: The Movie" playing the same character in the same situation.
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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