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on a cowboy boot 

What you say to someone when prompted with a question you don't know the answer to.
(During an infomercial selling a Panini grill.)
Kathy Mitchell: Do you like sandwiches, have you had a Panini before?
Steve Brule: On a cowboy boot.
(Infomercial stops; awkward pause.)
on a cowboy boot by Nalyd1 July 10, 2010

The Brown Cowboy

This is the act of ejaculating deep inside a girls asshole without her knowing it's about to happen. As she becomes comfortable with a little fingering of the Brown eye as you fuck her, you make your move! Pull your pistol and saddle up her back door for the ride of a lifetime! It's certain to end with a bang! If she likes it, then youll know you found your philly!
The Brown Cowboy is the act of ejaculating in a girls ass without her knowing it's about to happen. Also used as a test to see if she's a keeper.

Bro! I think I'm I'm love! I pulled the Brown Cowboy last night and she liked it!

rootin tootin cowboy shootin 2

rootin tootin cowboy shootin 2 is just a better version of Red Dead Redemption 2
Let's play some rootin tootin cowboy shootin 2

dayvan cowboy 

An individual who boldly parachutes from the stratosphere down onto a surfboard in the ocean.
Bobby became a dayvan cowboy just last thursday
dayvan cowboy by battle_pope June 30, 2006

Censorship cowboy 

Someone who spends much of his time finding new and better ways to help others get around internet censorship or word filters. Often students or people in highly censored countries. Usually the people that believe firmly in freedom of information and free speech.
Kid: Hey, this suxxors, i can't get to youtube at school.
Censorship cowboy: Here, try this. It works every time.
Kid: Thanks man! You rock!
Censorship cowboy by Jason Zig February 24, 2008

TJ cowboy 

A dude from Tijuana, Mexico, wearing rustic Southwestern attire.
"TJ cowboys hang around - Sleeping in the sidewalk with a Burger King crown
Never wake 'em up - Mas cerveza - Til the rooster crows Vatos de gallos..."
TJ cowboy by jadawolf June 11, 2008