Going against the rules or set of norms. Breaking the mold, usually in a spirited or rebellious manner. Similar to "going rogue". Often times reckless or careless in their pursuits.
"Why do we have so many office supplies? 2000 red pens? 500 boxes of staples? We only have 10 employees!"
"Bob from accounting must be going cowboy with the credit card again."
"Bob from accounting must be going cowboy with the credit card again."
by Pappa Wayne May 23, 2019

the practice of not wearing underwear under one's outer clothing. also referred to as "going commando."
by mem13 July 01, 2008

To deliberately kill a number of random bystanders while performing a criminal or political assassination. It gets the message across that you really wanted the person
dead. The target was known to frequent a certain bar, so they went cowboy on the place and took him out.
dead. The target was known to frequent a certain bar, so they went cowboy on the place and took him out.
by man with titties January 05, 2017

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.
by Thatplayer58 January 20, 2021

Jack went cowboy and got the job done, pissed people off and broke a couple of ribs doing it though.Going cowboy isn’t for the weak of mind.
by Outlaw78a February 05, 2020

An answer to anything. No matter what context, no matter what question. But most importantly, it’s the answer to questions that don’t matter.
by Thatplayer58 January 20, 2021
