The 25 Realest Rap Songs About Prison

WC and the MAAD Circle "Out on a Furlough" (1991)

Producer: Sir Jinx, WC, Crazy Toones
Album: Ain't A Damn Thang Changed
Label: Priority

His primary contribution to mainstream America may have been the career of Coolio, but W.C. and the Maad Circle's debut LP was a classic to west coast hip-hop heads. One of its best tracks is "Out on a Furlough." The protagonist kicks it at a party with an old friend; when the drinks run out, he's conscripted to join Joe and his Pinto on a trip to re-up. The police pull the duo over, discover cocaine in the back of the ride, and because W.C. is no snitch, he ends up sentenced to five years on the inside.

Ultimately released on a furlough, W.C. survives his prison term thanks to the advice of a "brother named Black," who ran the yard: "Told me, 'bust a funky rap, you won't need a bodyguard' / Don't get me wrong, y'all, I'm far from soft / but for the next six months, I was rappin' my ass off." —David Drake

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