Drugsto' Cowboy

A popular internet blogger, vlogger, and music video comedian, The Drugsto' Cowboy is the self-proclaimed "most color-coordianted rapper to ever come out of Sheboygan, WI."
"The Drugsto' Cowboy has more game than a Jewish Community Center on BINGO night."
by Dave Lahna December 31, 2008
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Yooper Cowboy

People from the U.P who dress in a flannel, work boots, and a Stormy Kromer while sometimes carrying a gun.
Yo what's with all these Yooper Cowboys lately?
You can tell when it's buck season because the Yooper Cowboys come out in full force.
by tilsby November 13, 2018
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kotex cowboy

1. A person who is a pussy
2. Someone bitches a lot
3. A person acting in a cunt like manner
by God's Gift To Electrical December 18, 2013
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river cowboy

Rugged men who work on the inland river system- loading, unloading, and towing barges of cargo. They can tie a line, fetch a wire, and will work 365 days a year.
“Hey, It’s time to switch these barges out at the dock. I’m gonna need some river cowboys to help flip this load out and tumble one of those empties in”
by Flat Dick October 05, 2018
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Go Cowboys!

It’s the answer to dumb questions or questions you do not want to answer. Mostly to personal questions, but this is the answer to any serious question.
Frank: Hey Gary how do you feel about the upcoming election?
Gary: Go Cowboys!
by Thatplayer58 January 21, 2021
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Penis Cowboy

Somebody who rides the penis much like a cowboy rides his horse
Wow... look at tim cook... such a penis cowboy.
by TheFridgeMaster December 01, 2009
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Steamroom Cowboy

A gentleman who enjoys loitering in steam baths in the company of other nude men, for any number of other reasons - mere voyeurism; the prospect of a good, hearty romp with another like-minded fellow; or possibly he wants to check out the other chap's todger to see if it matches the description of the one his wife has been playing around with.
When the Ambassador caught Alex hanging around the steam baths, peeking at stray John Thomases, he proclaimed him to be a "Steamroom Cowboy".

Naturally, the Ambassador thought nothing of keeping the photographs of this behaviour.
by Hangus the Monkey September 29, 2019
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