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cowboy rich 

Soldiers, forest rangers, fisherman, and other workers who get paid in one lump sum after a long season of work become "cowboy rich" on payday. Usually connotes blowing all the money on a whoop-it-up session in town.
Those mean bastards from the Bar K ranch will be cowboy rich on Tuesday, but they'll drink all the money by Saturday night, shore 'nuff.
cowboy rich by Tikaro April 23, 2003

cowboy shit 

to do something reckless without concern for the consequences.
This nigga Rob was on some wild cowboy shit last night til the cops showed up.
cowboy shit by Chain6an6James February 14, 2014

Cowboy-popsicle 

A frozen rope used for anal sexual pleasure between to male partners.
Adam beat Jim in tug of war with a cowboy-popsicle last night.

Cowboy Bebop 

The Show Created in 1999 by Shichiro Watanabe that depicts the life off 4 space aged bounty hunters (Spike, Faye, Ed,Jet) in the year 2071.
The Best AnIme Eva~~
Cowboy Bebop by Lady DeathStrike December 5, 2003

cowboy caddilac 

A 4 door 4X4 pick-up. Probably with a lift kit. Also known as a redneck limo
Hey Jim Bob, you fixin to drive down in yer cowboy Caddilac?
cowboy caddilac by Frank J. August 6, 2007

Cowboy Beard 

Dean-Anthony, button your shirt, nobody wants to look at your cowboy beard.
Cowboy Beard by RickyWaynthBishop January 11, 2012