In case you’re a Portlander who’s been living under a rock, Sina Wynne Holwerda, known simply as Wynne, is a Lake Oswego-raised University of Oregon grad, and rapidly rising hip-hop star based in Portland. Here at the Mercury, we are certified card-carrying Wynne stans, initiated into her “Hunnycomb” fanbase even before her excellent 2019 debut full-length If I May...

Wynne’s world has been a whirlwind the last several years, and we’ve been trying our best to keep up. Ahead of her upcoming Hunny I’m Home show at Wonder Ballroom, which wraps her headliner tour, we sat down with the emerging rapper to discuss her album, her tour, and her career's steady, hard-won climb. 

The rapper first began turning heads in 2017—raising eyebrows with a show-stopping freestyle at a Mic Check-sponsored cypher, impressing listeners with her lyrical prowess, and taking hard progressive stances on early songs like the 2017’s “CVTVLYST,” and “Open Letter to Donald Trump.” 

Since 2018, Wynne has been managed by Courtney Stewart of Right Hand Music Group, who Wynne credits for a lot of her success and her team's strategic business moves. In 2020, the artist had a formative experience supporting Atlanta hip-hop duo EarthGang on their “Mirrorland” tour. The next year, Wynne dropped an EP Do My Own Stunts with producer Christo. She’s collaborated with big names like former Portland Trail Blazer and rapper Dame D.O.L.L.A and soul singer Mahalia, as well as JID on “Ego Check,” even making a song for her alma mater, “Throw The O (The University of Oregon Women’s Basketball Anthem)” in 2022. Flanked by business partner and audio engineer Itay Lerner, the blonde-haired rapper has continued to sharpen her pen, hone her delivery, perfect her aesthetic, and expand her reach while remaining committed to supporting—and residing in—Rip City.

Related: Rap Goddess Wynne Talks New Album, Rose City Loyalty, and Touring with EarthGang

2023 has been a real year of Wynning. In April 2023, the Wynne team began rolling out ger new EP Some Like It Hot, preceded by red-hot singles “Jaw Morant,” and “Hot Friend.” The artist continues to drop stellar music videos for the songs, some of which have premiered via World Star Hip-Hop.

Considering this very intentional and aggressive rollout, the headliner tour announcement made perfect sense, and excited the emcee’s rapidly growing fanbase. A team of six helped pull off the Hot On Their Heels tour: DJ and hypeman Rafael “Raf” Newman; tour manager Itay Lerner; Blossom (AKA Keisha Chiddick) performed a slew of roles including front of house, hair, and stage management; agent Cara Lewis; Riley Brown who handled all the content, and assistant tour and merch manager Jordan Holly. 

Wynne described her first headliner tour as “probably the most surreal experience so far in my career and my life,” and something she had dreamed about since she was nine or ten. “To be the headliner, to have the greenroom, and to be able to have the team and my friends and my sprinter van… it was just totally different. We had obviously done the support tour with EarthGang. I don’t think any of us were prepared for how different being the headliner would be. It was a lot of work and worth all of it. I was so nervous going into it like: What are these shows going to be like? Who are these fans?” 

Wynne’s setlist included a healthy mix of old songs like “Don’t Touch,” and “Buzzer” and new standout tracks “Jaw Morant,” “Hot Friend.” Some Like It Hot is a no-skips situation, and Wynne told the Mercury it’s just the beginning of what will later become another full-length.

“I think a big motivator for this project was it’s actually the first part of two EPs; they’ll go hand-in-hand together,” she said. “Some Like It Hot is, like, the post- traumatic breakup glow-up. It’s the rediscovery, re-finding confidence…. it was like, let me make the soundtrack to my confidence, let me make some records that me and my girls can pre-game to, like records that I want to dance to in the club. Let me talk about some of the fun times before I get into the shitty stuff.”

The project certainly feels like a girl’s girl, providing repeatable mantras and curve-em slogans—it’s no wonder fans ate the lyrics up and have been joyfully spitting them out, in unison, at shows around the country.

“‘Jaw Morant’ and ‘Hot Friend’ are super fun [live]," Wynne said. "I was honestly blown away by how many fans knew the words. Like, I don’t think once on the whole tour did I ever say ‘I’m a mutherfuckin dog/ Mirror on the wall, who’s the baddest of them all.’ I could just go: ‘What!?’”

Wynne is signed to Genius (they do more than lyrics) for distribution, and a connection provided by Genius’ Rob Markman landed Wynne on radio show Sway in the Morning. There she delivered an outstanding freestyle verse over the beat to Drake’s “Lord Knows.”

“[Being on Sway’s Universe] was like, I’ll never forget that in my life,” Wynne recalled. “I’ve wanted to do that since I was a kid… When he walked in, I just started crying.  It was like that.”

Her upcoming tour finale represents a full-circle moment for Wynne fans. Back in December 2019, Wynne's first Hunny I’m Home show at Hawthorne Theater featured special nature-inspired displays like an onstage beehive, giant teddy bear, and a vine installation. Wynne says the tour’s upcoming finale will also have certain additions to make it special. 

“We wanted to make the hometown show feel special, feel different," Wynne said. "And it felt like the right amount of time to do some re-thinking, and go ok, we want to have another Hunny I’m Home, have a big hometown show. I haven’t played a headline show since 2019. Bigger venue this time, trying to go a little bit harder. The music has changed, I’ve changed as a performer.” 

Wynne acknowledged her own earned confidence on stage, saying "I've always had a really raw skill, but it took me some time to hone that in and learn who I was." It's also worth considering that her last over-the-top home show kicked off pre-pandemic. When everything shut down, Wynne was just 22 years old. "This has just been my early 20s," she explained, "growing into the woman I am, and going through life experiences that have shaped me. So now, when I get onstage, I'm really focused. I’m not so much focused on survival."

She credited time spent in the gym with improved breath control: "Before, I felt like I was thinking so much about what I was doing while I was onstage. And now it feels a lot more natural and confident, because I've removed some of those obstacles, like not being able to breathe."

The now 26-year-old artist shrugs off comments by those who are uncomfortable with her sexier, more grownup image, saying her aesthetic is the natural result of just that: growing up. “This was less an artistic decision I made, and more just, like, I grew into a woman. When most of these people found me I was a teenager, and that’s the life I was living. I was a backpack rapper. And I’m still a backpack rapper. That’s still my roots and that’s what I do… but now I’m a 26-year-old woman, and I fuck. And so," she said with a laugh, "I make songs about it.” 

Coming up around the bend, Wynne says there’s lots for fans to look forward to, including a music video for “Wife,” and a second EP around Spring 2024. In the meantime, there are somehow tickets still available for her homecoming show. The all-ages finale that is technically part of Wynne's Hot On Their Heels Tour, but the artist said to expect a different setlist and special surprises for the Portland homecoming. Some will come to see or support what Wynne has up her sleeve. Others will want to know what all the hype is about, but we're willing to bet most people will leave feeling impressed.

Wynne: Hot On Their Heels Tour hits the Wonder Ballroom, 128 NE Russell, Thurs Nov 16, 8 pm, $25, tickets here, all ages