33. Ice Cube "My Summer Vacation" (1991)
Album: Death Certificate
Producer: Boogiemen & Ice Cube
On "My Summer Vacation," Ice Cube, a known gang affiliate, devises a clever solution to the constant harassment he gets from the police - he takes the first plane out of Los Angeles to St. Louis, and establishes himself there by uprooting local dealers from their corners. He makes a killing for a while, but it doesn't take very long for him to get embroiled in a full-on gang war that lands him in prison with no hope for parole. "My Summer Vacation" maps out the spread of the crack epidemic and its attendant gang violence across the country in vivid detail, putting a personal spin on the trail of death and addiction that plagued the country in the '80s.