6./7. Vinnie Dewayne

6./7. VINNIE DEWAYNE 

POINTS: 45

FORMED: Started performing in 2009.

SOUNDS LIKE: Kendrick Lamar's cousin who really got into The Warm Up-era J. Cole but wanted more atmospheric beats.

Vinnie Dewayne is feeling good. Driving home from his new job teaching at-risk youth at Open Meadow, an advocacy-based North Portland education program, the 24-year-old rapper talks with pride about the 10 students he worked with that day. 

"I had them write a verse today that had to use four metaphors and four similes," he says. "I feel like when I heard their stories, I could hear the hunger. I could hear where they were coming from. It was a reminder to me: What's most important is my community."

It's a community he's relied on often throughout his life. Most recently, when the St. Johns native returned to Portland after graduating from Chicago's Columbia College with a degree in business management, he was sleeping on friends' couches—another new graduate trying to find a job in a quickly transforming Portland.

Dewayne, whose pursuit of a college degree earned him the nickname "the St. Johns Scholar," raps with a casual ease on the mic in a voice reminiscent of a younger Kendrick Lamar, the well-rehearsed product of 10 years of experience in the recording booth. But it's not just his tone and an excellent taste in R&B-inflected beats that have attracted collaborations with a who's-who of Portland hip-hop over the past few of those years. It's the words themselves.

"I clocked into the studio with Chris Barnett/'Cause last night I had some shit up on my chest," he raps on his Rites of Passage EP, the prelude to his upcoming album, Saint Johns Scholar, scheduled for release in early summer. "I was on the phone with my mama, she stressed/The doctor says she's worried too much/She ain't paid rent.” 

His willingness to share real-life experiences with such stark candor has made Dewayne one of the best young rappers in Portland. But he's no longer content to communicate his experiences alone.  

WWeek 2015