cowboy face is a frat star drinking game originated at the University of Virginia. The rules are simple: shots of whiskey, preferably bottom shelf bourbon, are passed around. Everyone rips the shot after which each person, resisting the need for a chaser, presents to the group their best "cowboy face". Whoever grabs for a soda / smirnoff ice / beer first loses.
Typical Cowboy Face situation: Yo broh, we just got a bottle of Jim Beam Black. We're about to go to a Pi Phi social. Anyone wanna play cowboy face?
by T-$$$$$$$$$$$$$$$ June 05, 2010

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