Given his gangsta rap background, this is one of Snoop Dogg's least shocking facts. He supposedly joined the Rollin' 20 Crips, one of Long Beach's most popular gangs, as a teenager. Law enforcement knew him, even though he denied being a gang member, especially when his music career took off. Snoop was jailed for various offences, including narcotics offences, between 1989 and 1993. New York Times