What is Massachusetts Cowboy?
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A person who was born and lives in Massachusetts, but for some reason dresses like a cowboy. Usually a symptom of dementia from too many years of drinking.
Person 1: Why are you wearing cowboy boots and a cowboy hat?
Person 2: Because I grew up on a farm in Massachusetts.
Person 1: Oh, your a Massachusetts Cowboy.
Person 2: Baaaaaaaahhh!!!
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