3. Blossom (70 points)

SOUNDS LIKE: Fantasizing about the underground nightclub of your dreams, discovering it actually exists, then staying there all night.

NOTABLE VOTES: DJ Klyph; past Best New Band finalists Tope and the Last Artful, Dodgr; Holocene booker Gina Altamura.

At age 27, Keisha Chiddick has already lived many lives.

So many, in fact, that she can break them up into specific eras. There's the Found Years. The Slap Years. The Grounded Years. The Boy Years. Right now, she's in her Sassy Years.

"I'm very reflective," says the singer known in Portland as Blossom. "You live a lot of different lives in your one life. I like to think of the turning points in my life that made me who I am."

For Chiddick, who was born in the island nation of Trinidad and Tobago, there have been many of these turning points, all of which have brought her to where she is now, as one of Portland's best R&B artists. The first came when she was 5 years old, when she moved to the United States. Her dad had come to Seattle to play in her uncle's steel drum band when Chiddick was just a baby, and came back, along with his new wife, to bring her, too.

"It was a culture shock," she says, "and had a lot to do with me learning and growing up. I was the only black kid anywhere. I had a thick accent. I was a foreigner."

As she grew up, the family moved often, and Chiddick got in trouble—a lot. Her dad decided to send her to live with her uncle in Tacoma for the summer. It was there that she learned to play the steel drums. "I was just obsessed with it," she says, "and I was pretty good." During the summer, she would play in her uncle's band, traveling to gigs across Washington. She stopped when she was a teenager because she didn't think it was cool anymore. She also had terrible stage fright, refusing to even look at the audience. Singing was completely out of the question.

In her 20s, Blossom moved to L.A. and quickly joined an R&B girl group. Even more quickly, she realized it wasn't for her.

"I describe those times as the Slap Years," she says. "I got so many slaps in my face that woke me up and made me realize what I wanted to do, which I needed. I would never take any of those years back, because I moved home and started my career."

Returning to Portland in 2013, she met producer Neill Von Tally and rapper Ripley Snell at an album-release party. "They were like, 'Let's do an open mic,' and I was drunk and was like, 'Let's do it!'" she says.

(Thomas Teal)
(Thomas Teal)

She went onstage and performed one of her songs, which caught Von Tally's ear. He went on to produce Blossom's two EPs: Sass, a jazzy R&B project, which is the best example of how she describes herself, as a rapper "who just sings it"; and last year's Wavves, a playful-yet-sultry collection that showcases her lyric-writing. Falling somewhere between dreamily romantic neo-soul and brassy hip-hop, Blossom's music has developed into a distinctly intoxicating stew, marked by velvet vocals, playful lyrics and airy beats reflective of her island upbringing.

Since connecting with Von Tally, Chiddick has continued writing music, going to shows, and working as a property manager on the side—letting things happen organically, she says, and not taking shit from anyone.

That brings us to her current phase.

"I have, like, zero tolerance for stupidity, by men or women, or politics," she says. "The Sassy Years mean standing up for myself and other people."

And that's what she's beginning to do with her music. In "Black Magic Woman," a reggae anthem she describes as a "shady political song," Chaddick sings, "Won't see it coming but just know the time is near/Black magic woman will come back to take back our rights to remain black."

"It is for black women, but it's an innuendo to the fact that all women are magic," she says. "It's contorted into black magic because we're strong. I'm very OK with being black magic."

NEXT GIG: March 18 at Mississippi Studios for WW's Best New Band Showcase.