It’s after midnight on a Wednesday night in April, and Rasheed Jamal, a member of the rap trio the Resistance, is talking to the crowd at Holocene, a Southeast Portland, Ore., club. “I know it’s late and we’ve all got work tomorrow, so I’m going to let you guys decide: Should we do one more song?”

There are about 30 people left in the audience, and they shout for one more. “OK,” Jamal laughs. “Now when I say ‘love,’ you say ‘hip-hop’…”

The message is a fitting cap for the show, a four-hour mash-up of local pop, rock, and rap acts, which is itself a call to action. Local record company Party Damage organized the night as a gesture of support for Portland’s hip-hop community and minority populations, who’ve been having trouble with the police bureau and fire marshal, reviving long-standing conversations about discrimination around town.

Portland, despite its reputation as a hub of young, progressive creatives, is also a city with a remarkable lack of diversity; according to the 2010 U.S. Census, 76.1% of its population is white. The city’s recent rapid development has led to a feeling of further marginalization among non-white communities, and those frustrations are being expressed vocally within the local hip-hop scene. But while that community feels it’s being targeted and pushed out, the city’s cops feel their actions are being misunderstood. Who is right, and is it possible for a black community to have a thriving voice in the whitest major city in the country?

Party Damage dreamed up this midweek party after another one, at an unassuming Portland jazz bar called The Blue Monk, was shut down. On March 1, three of the city’s most-loved rappers were set to perform there. The men on the lineup — party rapper Mikey Vegaz, self-proclaimed “King of the Northwest” Luck-One, and national freestyle champion Illmaculate — all in their twenties, have built up local cred after years of performing. Hyped around town as a showcase for The Heavyweights of local rap, the show sold out — but the unexpected arrival of the cops and fire marshal quickly shifted the tone, and spurred a citywide discussion of its treatment of the hip-hop community.

The first pair of police officers arrived 20 minutes into the night’s opening set. According to organizer and promoter Bryce Trost, the cops asked that Mikey Vegaz (born Eddie Bynum Jr.) be pulled from the stage for questioning. When Trost refused, he says, the officers threatened to shut the show down. “[The police] were trying to provoke something,” Trost says. “But when they saw — surprise!— nothing bad was going on, they started looking around, saying, ‘Oh, well, you know, this place looks pretty crowded.’”

The fire marshal was called to the scene to count heads, and over the course of another hour, a dozen additional officers, some members of the gang task force, arrived. Trost says the officers ignored his offer of an “accurate tally” from the box office attendant. Showgoers were ushered out; many were prevented from re-entering. Illmaculate, whose real name is Gregory Poe, took to the stage amidst the commotion, and announced that he would not be performing. Outside of the bar, located in the residential Belmont neighborhood, traffic was blocked by squad cars. No criminal activity had taken place.

For Illmaculate, who’s been performing since he was 17, the “overt display of authority” was familiar. The night before the Blue Monk show, police had interfered with a Black History Month event featuring rap performances at North Portland warehouse venue Odyssey. His refusal to perform at Blue Monk, he says, was about “frustration.” That night, he expressed disappointment on Twitter: “I will not perform in this city as long as the blatant targeting of black culture and minorities congregating is acceptable common practice.”

“The hope was to burst some bubbles,” says Casey Jarman, the co-founder of Party Damage Records, of the April Holocene show. He planned it in conjunction with an open letter in the Willamette Week in April, calling for Portland music fans to rally in support of the hip-hop scene. “Portland is a progressive but also really segregated city,” he says. “Not just racially, but culturally. I think that everyone involved with this show has expressed interest in breaking down those barriers and seeing what would happen.”

At the party, the bar serves a rotating selection of alcoholic slushies. Most of those in attendance, in oversize sheet tops, high-waist jeans and vintage sweaters, would fit in easily in the background of a Portlandia sketch. Tucked discreetly between the bar and the permanent photo booth, representatives from the ACLU of Oregon are manning a table stocked with wallet-size pamphlets on citizens' rights.