Is Portland’s Next Viral Rap Star a Babyface Blonde Girl From Lake Oswego?

Wynne knows you're skeptical, but that plays to her advantage—especially once she opens her mouth and gets to spitting.

Sina Holwerda knows what you're thinking, and she doesn't blame you.

"Anyone who's going to judge me before I rap, I understand why," says the 20-year-old Lake Oswego native, who rhymes under her middle name, Wynne. She's well aware that, as a babyface blonde girl from a wealthy Portland suburb trying to forge a career in hip-hop, the very sight of her is going to trigger eye rolls in those still suffering from post-Iggy Azalea PTSD. But she also doesn't deny that such skepticism plays to her advantage—especially once she opens her mouth and gets to spitting.

"It's a fun element of surprise," she says. "It's why I went viral."

Actually, it's the reason she's gone viral twice. In 2016, Holwerda posted a freestyle to Twitter, showing off the rapid-fire delivery and in-your-face lyricism she's been honing since middle school. It caught fire online, exploding her followership; even Snoop Dogg retweeted it. A few weeks ago, she put up another freestyle intended as a thank-you to those who'd supported her over the last year. It blew up even bigger. Preeminent hip-hop blog World Star picked it up, then Complex, then Beats 1 radio. She's now sitting at 48,000 followers and counting, received co-signs from such industry heavy-hitters as Irv Gotti and Post Malone, and even has fan accounts popping up on social media.

It's been a whirlwind, for sure. But if you ask Wynne, it hardly happened overnight. She's been working toward this since age 12, when she fully gave herself over to the rap life—writing lyrics every day and trying to match her flow to motormouths like Eminem and Twista—a decision that initially confused her investment manager father and attorney mother.

They started to take her more seriously around the time she entered her seventh-grade talent show. "Granted, I sucked," she admits. But she did catch the attention of a classmate's father, a former rapper himself, who told her she was "born with a gift." "I've hung on to those little comments throughout my career that have helped me stick with it," she says. Being underage in Lake Oswego, though, further opportunities to get onstage were rare. She watched the Portland scene from afar until earlier this year, when she performed at longtime promoter StarChile's monthly Mic Check cypher at White Eagle and blew several vets off the stage.

im just gonna rap for you real quick 🍯

A post shared by WYNNE (@sinawynne) on

With her profile increasing, Wynne recently scrubbed the internet of her older material, leaving only the scathing "An Open Letter to Donald Trump" and "CVTVLYST," a six-minute labyrinth of pop-culture references, political invective and shout-outs to fellow University of Oregon alum Marcus Mariota. A self-described "rapper's rapper," she's currently working on developing the pop side of things, like writing choruses, and fielding offers she's yet not at liberty to discuss.

Wynne knows that, for every Aminé who's able to spin clicks and likes into legitimate success, there are hundreds more who simply disappear into Google's cache. But the way she sees it, whatever happens, she's already put in too many hours to be considered just a flash in someone's timeline.

"I've been working at this for a while, and I didn't mean for this to go viral. I just posted a video of me rapping," she says. "If that's what it took for people to start paying attention, then so be it. But it's been a long time coming."