“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.”

This year promises to be a momentous one for the city’s hip-hop scene, but Mason, better known as Vakill, isn’t one of the handful of Chicago rappers–among them Bump J, Rhymefest, and Lupe Fiasco–who’ve been scooped up by major labels since the breakout successes of Kanye West and Twista in 2004. He doesn’t have a huge promotional machine pulling for him either–his second album, Worst Fears Confirmed, comes out Tuesday on the indie label run by the Molemen, the local crew he’s been running with for 15 years. But Mason’s new disc could easily end up being the best hip-hop record to come out of Chicago this year.

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.

The 30-year-old Mason was born on Chicago’s near south side and raised on 119th Street, in the heart of the “Wild Hunneds.” He was a big hip-hop fan by his early teens. “Growing up, I always checked for the guys who had a good choice in wording,” he says. “Back in those days it was kinda rare. But when you’d hear someone like T La Rock’s rhymes, he would always send me to the dictionary. Like, ‘What the hell does that mean?’ ‘Cause a lot of MCs wasn’t doing that–it was just your everyday slang put on record. But this dude was schooling you and giving you a new vocabulary. An artist like that will stick with you for the rest of your life. To this day I use the dictionary to make sure I’m on point, just ’cause of him.” More recently he’s taken inspiration from the delivery of Organized Konfusion MC Pharoahe Monch. “He’s the all-around best as far as style,” says Mason. “His approach to a beat is so off center, but it still rides. That’s the way I always try to come at it.”

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.'”

Zamudio and Mason soon started working together–it was Mason who christened the Molemen in the early 90s–and they’ve since collaborated on nearly all Mason’s releases. He put out a cassette, Who’s Afraid?, in 1995, and a year later he released “Keep the Fame,” a single with Percee P and Rhymefest. Mason also appeared on a series of Molemen comps, mix tapes, and collaborations, many of which were collected on his odds-and-sods set Kill ‘Em All in 2001. He compares the years between Who’s Afraid? and The Darkest Cloud to a training camp. “Day in, day out, all we were doing was making beats and writing rhymes–nothing else,” he says. “We were unemployed, in our moms’ basements, running up the electric bills, getting busy.”

The Darkest Cloud earned Mason a significant audience outside Chicago, but it hardly happened overnight. The album built up buzz over a couple years–which Mason takes as proof that it was ahead of the curve when it came out. “I just did an interview with XXL magazine off the strength of one of their writers finding out about it,” he says. “And we’re talking about an album that’s three years old! Everybody is just now learning about the record through word of mouth, hearsay, the Internet, what have you. The next shit is never accepted right off the bat.”

Zamudio agrees. “I know with Immortal Technique, his first album–it took people two or three years to catch up with it,” he says. “He put out his second one and people were barely getting his first.”

But Darkest Cloud’s long climb out of obscurity–which Mason didn’t want to abort by releasing a new album–is just part of the reason it’s been a three-year wait for Worst Fears Confirmed. “Three years, that’s a lot of growth. . . . My music needed to reflect that,” he says. “I could’ve easily told Panik, ‘Give me a whole bunch of junk Jeezy-type beats and I’m gonna go for mine and make 16 crack songs.’ Not to knock Jeezy, ’cause he’s got a tight album and he’s authentic–he’s actually lived that life. But that’s his niche, not mine. . . . I’m not gonna try and walk outside of my character and try to jump into that shit.”

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.”

If Mason goes mainstream, it’ll be because the mainstream comes to him. “I’m not really trying to break into the industry. If all that falls into place, fine,” he says. “A lot of Chi alumni have done already infiltrated the game, so I’m living through them.”

But he says that Worst Fears Confirmed has already started attracting attention–and Zamudio adds that Molemen Records has recently been contacted by a couple major labels putting out feelers. “Darkest Cloud kinda sold out of a curiosity effect, but with this one it’s anticipation,” Mason says. “I’ve never had that before. It’s got the grind of an underground record, but it’s got the polish of major-label material, which makes me optimistic. Who knows what can happen?”

Art accompanying story in printed newspaper (not available in this archive): photo/Lloyd DeGrane.