A man, typically one in a Ford F-150, who drives to their 9-5 desk job where they brag about how much of a badass they are, afterwards they go home to their wife who doesn’t want to have sex with them due to their small penis
Why does John wear a cowboy hat and drive such a big truck that he doesn’t need?
Oh he’s an Urban Cowboy
Oh he’s an Urban Cowboy
by BigDaddyBigBoy March 17, 2023

When a cowboy let's his horse ride him.
by Sew Donym February 20, 2020

by MiKe OXL0NG March 18, 2023

by Mason Skyler October 27, 2020

by reilei February 16, 2019

Lots of urban calgary cowboys at this event.
Usually wear a cowboy hat for max of 9 hours or one night a year .
Usually wear a cowboy hat for max of 9 hours or one night a year .
by THE ORIGINAL STRETCH July 9, 2022

Hey, look at these great paper cowboy hats, I found in the restroom. Try passing them out while at the airport, to strangers. Make up a sign that says, ‘Get, your free paper cowboys hats here’.
by Navydude83 March 18, 2018
