9.50am/pm is known as Cowboy Time, because if you say 'ten to ten' repeatedly, it sounds like a galloping horse - 'ten to ten to ten to ten to ten to ten to ten' etc.
Chap 1: "What time is it?"
Chap 2: "Ten to ten."
Chap 1: "Cowboy Time!"
Hasidic Jewish person often seen in full hat and garb in Brooklyn, New York
Bob: "Did you see that Brooklyn cowboy trying to hitch a ride?"
Alaina: "Yeah. He needs to get home before sundown. It's friday"
someone who saddles up his pony and gallups off to help people
lil cowboy hooked us up with some starbux!
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.
Getting tasered in the genitals.
Did you hear what happened to Pete? The cops were trying to taser his chest but his arms were in the way, so they gave him an Electric Cowboy instead!
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.
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.