[HIP-HOP] In the middle of his 2010 mixtape, Solitary, over a sample from Wings' "Band on the Run," 19-year-old Portland MC Vinnie Dewayne crystallized his home life. "My family different/ We don't talk a lot/ Just hi, where you going/ Be back at 12 o'clock/ And that's a trait I take everywhere else/ I ain't an outgoing person/ I just keep to myself."

Now 21 and home from Chicago's Columbia College for the summer, the MC from St. Johns says his home life is exactly the same as it was when he wrote “Four Walls.” 

But when Dewayne's on the mic, something inside him changes. 

"I feel like it's the only opportunity to express what's inside of me when I'm on the microphone," he says, arms crossed as he pulls at the sleeves of his Notorious B.I.G. T-shirt. "That's just where I feel comfortable. It's hard to explain."

Harder to explain is how the immensely talented young rapper found his voice—one that sidesteps his generation's swag-centric ear candy for brutal lyrical confessionalism and a clarity of vision reminiscent of East Coast rapper-poets like Rakim and Nas. Dewayne isn't entirely sure, either. He charts his obsession with hip-hop to age 6 and credits a mentorship program called Step-Up for turning his academic life around. When it comes to his flow, Dewayne credits his father—who occasionally shows up in his songs to deliver shards of tough love—for throwing away Vinnie's written raps when he was 14. He never wrote down another verse. "Now I memorize all my raps,” he says with a sly smile. 

More impressive than Dewayne's formidable delivery is his storytelling savvy—something that's on full display on Dewayne's latest mixtape, Castaway. On "Can't Lie," a wholly unglamorous story about theft, underage sex and entrapment, Dewayne is a 'hood Raymond Chandler, masterfully penning his protagonist's downward spiral. "To me, it's about the devil," he says. "He wants us to contribute to our circumstances. He wants us to accept them."

Elsewhere on the record, the devil is something a bit closer to home. "What it mean to live a dream when your brother been shot and stop breathing," Dewayne asks on "Come and Get Me," "and your mother feel pain they're not treating?"

For Dewayne, who admits his confessional style can be painful for him and uncomfortable for his private family (Dewayne was raised Jehovah's Witness), honest self-examination is a way to stay on the right path. In a way, he's grateful to have grown up under tough circumstances. "I observe it," he says of gang culture and hustling. "But I see a bigger picture. Growing up in St. Johns made me realize I had a chance."

Ironically, it was moving to Chicago that provided Dewayne with some much-needed stability. On scholarship money, he's able to live in the wealthy Lincoln Park neighborhood with three roommates. "All I have to worry about is music and school," he says.

Coming home remains complicated. And though he's proven himself the most promising young lyricist in Portland, Dewayne still wonders where it's all going. "Sometimes I feel like I should be doing all the swag and the cars and the girls," he says. "Sometimes I think I need to be more like my generation."

SEE IT: Vinnie Dewayne plays Mississippi Studios, 3939 N Mississippi Ave., on Saturday, July 21, with Dam-Funk. 9 pm. $13 advance, $15 day of show. 21+.