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The phrase "Smile now, cry later" refers to a kind of street philosophy that speaks to the underlying idea that a gangbanger should enjoy the gangster lifestyle of women, drugs, money, and power now, while he can, because the other shoe will drop soon enough and it will be time to cry in jail or in the grave. The theme is frequently depicted in gangster tattoos showing a laughing or smiling face juxtaposed against a second crying face.
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A generational gang family in Chicago:
http://www.cnn.com/video/?/video/us/2013/06/03/nr-howell-mutligenerational-gang-members.cnn
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