Top definition
A male who is either a gangster, reppin' there crew and or hood but dresses good and takes care of himself as a prettyboy would or a prettyboy with the gangster life also reppin' his crew or hood.
" Na fuck no that guy isn't a prettYboy he's GANGSTA"

Someone such as 50 cent or P.diddy might be considered a prettygangster

by O.P.G April 03, 2006
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