Wynne Phillip Quinn

Last year’s Portland Hip-Hop Day got rained out and moved from City Hall to the Skype Live Studio, where attendees celebrated the veterans of Portland hip-hop. I went for part of it—the turnout was kind of lame. That’s why I’m happy that this year’s bill, curated by StarChile, is a well-rounded representation of the city’s new wave. DJ O.G. One will be spinning tunes, with Stoopid Burger and Hana’s Authentic New Orleans Snowballs providing the eats. Here are the four fiery artists who’ll be rocking City Hall for the third annual Portland Hip-Hop Day.’

RASHEED JAMALI couldn’t be happier to see Arkansas native Rasheed Jamal headlining Portland Hip-Hop Day—he doesn’t headline nearly enough shows, in my opinion, even though he’s one of the most talented and hardworking artists out here. Lately it seems like Jamal’s tide might be turning—he recently dropped Indigo Child (U Ain’t the Only 1!), a gritty, 13-track project with several gems, and released a beautifully shot music video for his standalone single “Love Is the Highest Religion.” But it’s his authentic delivery, songwriting prowess, and impressive crowd control that makes him fully deserving of the bill’s top slot.

Rasheed Jamal Miss Lopez Media

WYNNEIt’s been a few months since I first profiled the “Queen Hunnypot” Wynne for Sneaker Wave, but she slayed another performance at Mic Check in July. A couple of weeks later she tweeted out an excellent video of herself rapping and it went viral—the clip’s been retweeted 42,000 times! Wynne’s been keeping her head down in terms of output, but that’s mostly because she’s still working on getting her degree from the University of Oregon School of Music and Dance while perfecting her sound and networking. She did, however, put her “Open Letter to Donald Trump” on Spotify and Apple Music. Luckily for us, this has become a great time for her to repeatedly visit Portland and prove her chops as an MC.

FOUNTAINEI’m still pretty jazzed about Fountaine’s latest LP, H.F.I.L. (Hell for Infinite Losers), which dropped this summer. The tracks are highly varied—there are lots of Pokémon references and “anime rap,” but he occasionally ventures out of his comfort zone to sing on tracks like the retro-vibed “Dressed to Kill.” Fountaine isn’t afraid to make an R&B song either, or to take production elements from other genres. A born-and-raised Portlander, he vividly recounts his personal struggles, like riding the wild waves of the creative process and coping with depression while trying to be a successful Black artist in this city.

BROOKFIELD DUECEBrookfield Duece has been quiet for a while now... I was a little concerned he’d returned to his hometown of Oakland and was never coming back! Most recently Duece put out a solid EP, One Day It’ll All Make Cents, and it struck me as more innovative and less mumbly than his previous releases, though his sound still mostly retains that Atlanta-esque, Trap Muzik quality. The Oakland- and Portland-based rapper is probably best known for tapping his cousin to feature on “I Wish I Could Tell You”—you know, that remixed song with a verse from Damian Lillard (AKA Dame D.O.L.L.A.) that served as his impressive live debut?!? Anyway, the cousins have collaborated on several singles, so Dame’s presence is warranted.