Producer: Howie Tee
Album: Youngest in Charge
Label: Profile

Chief Keef wasn't the first 16-year-old to stunt on wax. That's how old Special Ed was when his debut LP was released; Youngest in Charge sold half a million records on the strength of his debut single "I Got It Made," a celebration of his newfound wealth and security. Over a sample of Ripple's "I Don't Know What It Is but It Sure Is Funky," the MC spit boasts that had kids across the country identifying—or wishing they could. "Make a million dollars every record I cut" he boasted, a bit unbelievably. But he lived the fantasy so others could feel it vicariously, bragging about how every other week he had a brand new car, an island of his own, and even a solid gold bone for his dog. Just imagine what his Instagram account would have been like.-David Drake