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From Wikipedia:
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A gangster is a criminal who is, or at some point almost invariably becomes, a member of a persistent violent crime organization, such as a gang. As an adjective it can be used as an unflattering depiction of the violent and devious methods commonly used by mobsters, and the derived form gangsterism implies such methods as practice or habit. The term gangster is most commonly used in reference to members of the criminal organizations associated with the American offshoot of the Italian Cosa Nostra, the Mafia (sometimes called the Mob), and the American prohibition, such as the Chicago Outfit and the Five Families, and individuals such as Al Capone and Bugsy Siegel. |
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Preppy, also spelled preppie, is a chiefly North American adjective or noun traditionally used in relation to northeastern private university-preparatory schools, as well as those who attend some of America's prestigious private colleges and universities. These characteristics include particular subcultural speech, vocabulary, accent, dress, mannerisms, etiquette, and entitled (assuming privilege) life view. The term "preppy" is similar in formation to hippie or yuppie, and it had great currency in the 1970s and 1980s. The term first reached a wider audience in the 1970 film Love Story, where Ali MacGraw's character uses it as a derisive term of endearment.
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Gangster vs Police, 
