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1.
A slang word black people use for a white guy who hangs around them, loans them money they dont repay, and drives them around for free.

In prison, it's a word used by black gangs to describe white males who hide their weapons for them. This leads to washing clothes, and this usually leads to the cool white boy getting cornholed by the said black gang.

Most white people who get called this actually love it.
Tyrone: Mark drives me around all day and I dont pay him for it. I also fuck his wife while he's at work. He sure is a cool white boy.

Raheim: Yeah when we were in the pen, I used to cornhole him everyday, and he never made me use lube. He also liked it when I teabagged him. He really is a cool white boy.

If you voted for obama and you are a white male, you are most likely a cool white boy.
by vlad679 February 11, 2009