rudeboy noun2 •A male juvenile delinquent, originally in Jamaica in the 1960s.Leppo had been a rudeboy since his teens, earning his first three-month jail rap for vagrancy in 1971. — 2000 •A male enthusiast of ska music."I swear I've watched as much MTV Base an Juggy D videos as they have, but I still can't attain the right level a rudeboy finesse," bemoans Jas. — 2007 formsrudeboys