For North Portland rappers, the St. Johns bridge is not an Instagram icon but a barrier that symbolizes the wide gulf separating their world from the rest of the city. Straight Outta

St. Johns Rap from the city’s edge

Since hip-hop arose from New York’s poorest boroughs in the 1970s, rappers have become famous name-checking some of the country’s worst neighborhoods. Portland may not have a Compton or a Bedford-Stuyvesant, but for the young people who live there, St. Johns is hard enough. The North Portland peninsula at the edge of America’s whitest city is home to public housing communities, higher crime rates and a group of rappers who believe music is their chance for a better life. The best-known rapper to emerge from St. Johns is Illmaculate, who canceled his performance with other hip-hop artists at Blue Monk last week to protest the presence of police. He’s also one of few rappers in Portland to enjoy big commercial success.

Gregory Poe, who performs as Illmaculate, is best known as a battle rapper. But more than the high-speed cutdown contests, his real love is making music. His new album “Clay Pigeons” comes out March 11.

Rap production in this town tends toward DIY: homemade mix tapes and simple videos shot along Martin Luther King Jr. Boulevard. But the music coming out of St. Johns offers an important look at the city. The lyrics recast places many Portlanders know. For these rappers, the St. Johns Bridge is not an Instagram image but a barrier that symbolizes the wide gulf separating their world from the rest of the city. Vinnie Dewayne, an inspiration to many of the neighborhood’s hip-hop artists, tells it like this: “St. Johns,

Take away the bridge,

Rich people in the hills

Can’t feel how we live.” The studio New York has Puff Daddy and Jay-Z. Southern California has Dr. Dre. In St. Johns, most up-and-coming rappers got their start under the tutelage of a skinny white music teacher with a Blondie poster on his wall. Jason Margolis saw how his students at Roosevelt High School idolized rappers such as Notorious B.I.G., rags-to-riches types who started in the projects and ended in gold chains. The kids memorized Tupac’s entire catalog even as they struggled to pass their tests. They looked up to Illmaculate, then a Pier Park teen who dropped out of Roosevelt but won the 2004 national Scribble Jam hip-hop battle. Budget cuts sliced Roosevelt’s band program in 2005, but Margolis thought he could build a recording studio with grant money. Margolis opened his studio in a school utility closet. Kids piled inside. Dracey Ware, a 6-foot-5-inch junior who shared a three-bedroom apartment with 13 other people, rapped over a piano-and-violin beat he found online. “Problems” sounds light and catchy, but the lyrics tell of a boy yearning for the mother who abandoned him: “Never make her proud,

‘Cause she never be around.

She busy with her life,

So to ventilate the pain, he busy with the mic.” African immigrants angled for time to freestyle about refugee camps. Kids from Benson High School sneaked in to record. “Rap gives people a sense of hope, joy, that feeling of, ‘Oh, somebody is hearing me,’” said Egbevado Ananouko, who raps about the New Columbia housing development. “A lot of people coming out of poverty, we’re always hoping somebody listens, somebody picks me.” The teens hung around for hours after school. Reminiscing with Ware recently, Margolis said he would stand outside the studio eyeing the clock. He needed to get home to his wife and kids. “I’d walk in that studio,” Margolis said, “and you guys would look at me like, ‘Really, really? Just one more track!’”

The North Portland peninsula at the edge of the country’s whitest city is home to public housing communities, some of Portland’s highest crime rates and a slew of rappers who believe music is their chance for a better life.

Documentary-style rap Coffee shops and a gelato purveyor are slowly changing the neighborhood’s tenor, but St. Johns’ median income remains $10,000 less than the rest of the city’s. Three-fourths of Roosevelt students qualify for free or reduced-price lunch. That’s the Portland that appears on Dewayne’s album “Solitary.” Dewayne’s songs are slower than the rap that usually tops charts. His deep voice crawls over minimalist beats, pianos plucked and drums delivered in spaced-out thumps. The languid pace is intentional: Dewayne is a story-teller, not a party-starter. The songs on “Solitary” turn the lens on Dewayne’s neighbors. In his lyrics, they dodge bullets and sleep on benches. He describes a homeless teenager riding the bus past Roosevelt in “Pour It Out”: “You see your teammates.

They still playing hoops.

You see that point guard.

You taught him how to shoot.

They going off to state.

You shoulda went too.” The narrator in Dewayne’s songs dreams of buying his mother a home on the other side of the bridge. But fans say Dewayne’s songs about St. Johns gave their bleak neighborhood cache.

St. Johns has birthed a generation of rappers who rap about the places that shaped them.

As teens passed Dewayne’s album around, others started working the neighborhood into their lyrics. They filmed music videos in front of the bridge and wrote songs about gentrification. One group named itself “Woolsey Entertainment” after the street in New Columbia. This documentary style of rap is different from the hip-hop coming out of other Portland quadrants, said Mac Smiff, editor of the regional rap publication We Out Here Magazine. Northeast Portland has poverty, too, but St. Johns emcees turn hard-scrabble tales into something more. “In Northeast, it’s ‘Hey, I’m from the streets, and I rap.’” Smiff said. “In St. Johns, it’s, ‘Hey, I’m from the streets, and I enjoy art, and I’m going to express myself.’” The neighborhood celebrity In other genres of music, Portland is a place you move to become successful. In rap, those looking to make it big say they have to leave Portland. The March 1 incident with police at Blue Monk is the norm for hip-hop here, performers say. Illmaculate vowed afterward never to perform in the city again “as long as the blatant targeting of black culture and minorities congregating is acceptable common practice.” No Portland rapper has reached Top 40 fame. But St. Johns kids who get as far as making an album are neighborhood celebrities. Dewayne, the rapper who made St. Johns references cool, is one. Dewayne visited Roosevelt’s poetry club last spring while on break from college in Chicago. Zay Gaston was a Roosevelt senior and decided to cancel a Taco Bell job interview to attend. Gaston, tall and dreadlocked, stuttered as he approached Dewayne. “I just have to tell you. I have to tell you. You’re like my hero,” Gaston told him. “‘Solitary’ saved my life. And it made me feel that much better because I was like, ‘I know him. You’re from where I’m from.’” When Gaston finished, other students had questions. Tell us about the money, they said. The scholarship. Dewayne’s songs helped him land a Gates Millenium Scholarship, the Bill Gates-funded ticket anywhere. It pays for his tuition at Columbia College in Chicago where he’s studying rap music management, as well as for his plane tickets home and any future schooling. Dewayne hasn’t made enough to put his mother up in the West Hills yet. But at half a million dollars, the scholarship is a start. Next » 2. Illmaculate