“The thing about Chicago MCs,” says Donald Mason, “the reason why we’re being embraced right now, is that we ain’t selling crack rock and aiming nines at your head for 16 songs straight. We giving people real hip-hop: straight conversation, introspection, battle shit, political shit. You getting it all.”

Best of Chicago voting is live now. Vote for your favorites »

Mason’s 2003 debut, The Darkest Cloud (also on Molemen Records), was dizzyingly dense–the product of an MC eager to work out years of musical and lyrical ideas all at once. Worst Fears Confirmed, on the other hand, is confident, refined, and focused. The Molemen’s production is lush and epic, studded with sound-track strings and samples from old-school 70s soul and funk, but it’s not so busy as to distract from Mason’s crisp rapping and quick wit. (The album also includes memorable appearances from the likes of Ras Kass and Royce da 5’9″.) Mason tackles hip-hop politics, taking braggarts like Jay-Z and Nas down a peg and advocating for virtues like skill and creativity instead of guns and money. He also steps outside the conventions of street rap to comment on the way social and economic forces have shaped the gangsta role–a dead-end character that’s been pumped up into a lurid cartoon by so many other MCs.

In 1989, when he was a freshman in high school, Mason met Ed Zamudio, now better known as Molemen cofounder Panik. “As soon as I heard him, I knew I had to work with him,” says Zamudio. “Even back then, he always kicked those crazy rhymes. I was like, ‘I gotta record this guy.’”

Mason doesn’t pretend to be an angel in his lyrics, but neither does he hold up anything he’s done as evidence of his authenticity. On “No Mercy,” a track from the new record, he raps, “What’s the definition of real? What counts as hot? / Never did a bid, never been shot / Never sold an ounce of rock / So if that amounts to props, sorry to hear that / Don’t give a fuck if you bounce or not.”