The next rapper to break out of Portland's hip-hop scene could very well be Wynne.
At least, according to Damian Lillard, who last month shouted her out on the Tidal podcast Rap Radar, hosted by music journalists Elliott Wilson and Brian "B.Dot" Miller.
"As far as Portland goes, that's the best co-sign you can get," Wynne says. "Dame inspires me in a lot of ways. It makes me feel humble and hungry."
That a blond woman who grew up in Lake Oswego could be one of this city's best rappers may have raised eyebrows when she came onto the scene a few years ago, and still might for those who have never heard her rhyme. But in the past three years, the MC has proved she's got the chops to rise to the top of Portland hip-hop, and even beyond it.
This week, she releases her debut mixtape, If I May. The title, she says, comes from an awareness of the culture she's entering as a white rapper.
"The title If I May is posing a genuine question to hip-hop, like 'Can I do this?'" she says. "White people, we come in and take things. And as a guest in this culture, it's important that I approach it like, 'I know what this looks like, let's talk about this.'"
Twenty-two-year-old rapper Sina Holwerda, who goes by her middle name Wynne, says hearing Lillard herald her as the next big thing in Portland hip-hop was one of the most exciting moments of her career so far. That says a lot for an MC who has been rapping since she was in the fourth grade, and whose come-up has been marked by bite-sized, viral glimpses of her skill.
The first time Holwerda went viral was in 2016, when Snoop Dogg reposted one of her freestyles on Instagram. Then, when she reposted the same video one year later, she gained 70,000 followers overnight, including Ty Dolla Sign, Post Malone and dozens of A&Rs. Suddenly, she was answering about 300 emails a day. Soon after, she signed a publishing deal and got a manager. Her team was all in place by the time she went viral a third time almost a year ago, when people mistook her for Eminem's daughter in a video that circulated on Twitter of Holwerda performing at the local hip-hop showcase Mic Check. Those big moments have been peppered with even more "holy shit" moments, like Missy Elliott following her on Twitter, Timbaland DM'ing her, saying he can't wait to work together, and others that Holwerda says she can't even talk about yet.
In the year leading up to her first full-length release, Holwerda has doled out six singles of laser-cut lyrics, unrelenting rhymes and fierce dexterity. Last month, she released a video for "The Thesis," named after a monthly local hip-hop showcase, featuring local luminaries Vursatyl, Illmaculate, KayelaJ and Lillard, aka Dame D.O.L.L.A., together in Pioneer Courthouse Square. Two weeks ago, she dropped "Ego Check," with Atlanta rapper J.I.D, which was streamed more than 200,000 times in a week.
Both "The Thesis" and "Ego Check" are two of the 12 tracks on If I May. Out Oct. 25, the mixtape boasts a credit list that includes Grammy-winning producer Hit-Boy; DJ Dahi, who's produced albums for Drake and Kendrick Lamar; and Sounwave, who's worked with hip-hop heavy hitters Lamar and Schoolboy Q, and on most of the Black Panther soundtrack.
The mixtape is largely about "the tales of being Hannah Montana for the last couple of years:" the surreal juxtapositions of attending the University of Oregon full time while establishing a rap career, like doing her first red carpet at the BET Hip Hop Awards and then flying home to take midterms, or meeting her idols and then learning about them in classes.
Holwerda's idols didn't go to college, and she didn't want to, either. After her first year, when Holwerda's parents saw her musical career taking off, they told her she could leave school. She decided to stay because of her social justice-oriented classes.
"If I didn't take those courses, I don't know if I could trust myself with the education I had prior to college to go on radios and really be an advocate and an ally," she says. "If I can do that, college was worth absolutely everything."
After graduating, Holwerda moved back to Portland. She says it's important to her to help establish Portland's hip-hop industry, which she says is Lillard's mindset as well. She lives in Northeast Portland and built a studio that she invites other artists to use as a creative space. But here, Holwerda doesn't just want to make it in her hometown, she wants to help put her city's hip-hop scene on the map.
"Portland needs representatives, and there's a space for that here because it's an underdog city and I'm an underdog. I want to help establish more of an industry scene here," she says. "There's so much happening that it's kind of the perfect time."
HEAR IT: If I May is out Friday, Oct. 25, across multiple platforms.