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drugstore cowboy 

a word that originated in the 1920s, describing a guy that constantly tries to pick up on girls... not necessessarily successfully.
jay and silent bob are unsuccessful, yet HOT drugstore cowboys
drugstore cowboy by nonsense August 12, 2003

Drugstore Cowboy 

A popular internet blogger and vlogger, known for his retellings of near-misses with the moderately attractive "ho's" that he attempts to score with throughout the San Fernanado Valley.
The Drugstore Cowboy is recognised for his creative vocabulary when identifying different types and attributes of the female and her anatomy.

See also "Drugsto' Cowboy" in Urban Dictionary.
"She started askin me all kinda questions about Terrance but I wanted to keep the conversation on the two of us so I broke teh news to her about his lazy eye and how he smells like Fritos."
-From the blog, "Ho's and the Olympics" by The Drugstore Cowboy
Drugstore Cowboy by Ryan Bodel January 3, 2009

drugstore cowboy 

A man who hangs around drugstores, mainly to impress woman.
Drugstore cowboys are not really cowboys at all. They are womanizers.

drugstore cowboy 

Rebecca met her drugstore cowboy in the alley that night.
drugstore cowboy by Justin April 6, 2005

Drugsto Cowboy 

A popular internet blogger, vlogger, and music video comedian, The Drugsto Cowboy is the self-proclaimed "most color-coordianted rapper to ever come out of Sheboygan, WI."
The Drugsto Cowboy has more game than a Jewish Community Center on BINGO night.
Drugsto Cowboy by Ross Bailer January 4, 2009

Drugsto' Cowboy 

A popular internet blogger, vlogger, and music video comedian, The Drugsto' Cowboy is the self-proclaimed "most color-coordianted rapper to ever come out of Sheboygan, WI."
"The Drugsto' Cowboy has more game than a Jewish Community Center on BINGO night."
Drugsto' Cowboy by Dave Lahna December 31, 2008