Wynne steps in, draped in improbabilities. Portland’s best new rapper is a blonde girl from Lake Oswego. She goes bar-for-bar on her new mixtape, If I May, with Blazers all-star Damian Lillard, aka Dame DOLLA, the best rapper in the NBA. About to embark on a nation-wide tour with some of the best acts in hip-hop right now—she’s here, back home in South West, putting on for her city harder than just about anybody. Then she starts to speak, and you realize that probability has nothing to do with it. Wynne just works harder. Her easy smile belies the kind of drive that has put her in the room with some of the best rappers and producers in the game, and now that she’s in a position to be heard, she isn’t going to take it lightly. Her goal has always been to shine a light on a scene that’s been growing here in Portland for decades, and you can tell her loyalty to this town run deep. I sat down with Wynne to talk about her relationship with the internet, her new Mixtape, and her plans to keep Portland in the center of it all.
Eleven: So, growing up in Lake Oswego, what was your first exposure to hip-hop? Was there a moment, or a particular song that you remember hearing?
Wynne: When I was growing up, my dad played a lot—he mostly played Luther Vandross, a lot of Black Eyed Peas when they were getting started, so I was always kinda more attracted to drums that hit, live bass sounds. He played a lot of Alicia Keys. My brother and I shared an iTunes account, so I had access to all his music, and when I was nine I went to make a warm-up CD for our soccer team and I asked him what to put on it. He played “Lose Yourself,” by Eminem, and I was like “This is insane!”
11: You first got on people’s radar when a few of your freestyle videos went viral. The first big one got reposted by Snoop. Were you making those for a while before that happened?
W: No, it was weird. That was the first one I made. It was for the “So Far Gone” challenge, and I just posted one, cause I thought I could kill it, and it circulated on Twitter. It started getting retweeted by these big accounts, all these meme accounts. Then Snoop Dogg posted it on Instagram and it blew up on Instagram and Facebook. It was weird.
11: Then there was the other infamous video where people thought you were Eminem’s daughter. We don’t have to get into that, I think Illmaculate set the record straight on that. But I wanted to ask, what’s your relationship like with the Internet these days?
W: That’s a good question (laughs). I always thought, you know, this is gonna work, I’m gonna get discovered and build my team and tour and become a rapper. But I had no idea how that was gonna happen, and I should have figured that it was through going viral a couple times, because I’m clickbait. It’s easy to see a white girl rapping and click on it to make fun of it, and then be shocked, and I end up getting followers out of that. So I’m grateful for the Internet, because it helped me connect with my team. But I don’t really like the Internet. I don’t really like Facebook. I love Twitter, but I don’t tweet, I don’t feel like I have anything to say. I like Instagram but I don’t post. I’m trying to get better about it. That’s a really vague answer to your question (laughs).
11: No, I think everybody has this complex relationship with all these things, like, “This seems weird and evil but I gotta be on it.” Anyways, last month, you dropped your long awaited debut mixtape, If I May. How has that been, having that out?
W: It’s been really cool. It’s definitely weird to live with those songs forever. It was really just Itay and I locked in the studio for about a year working on those songs. Each song went through so many different lives, so then to give that to the fans—I mean, we’ve each seen twenty drafts of these songs, and we’ve seen ten different versions of the tracklist, so to give it to people and really say, “We’ve done everything we could do, this is the best work we could make, we’re really proud of it,” and to see how stoked the fans are and how much they love it, there’s really nothing like it. It’s really special.
11: So you were saying there’s been a lot of versions of these tracks, and one thing that I appreciated about If I May, is that compared with some of your older tracks, the songs here feel more like songs, in terms of their structure. If you look at a track like “CVTVLYST,” a few years ago, that’s just six minutes of solid bars, which is dope, but now you have a better sense of, “Okay, there’s a hook here, there’s a switch-up here.” Was that something that you had to work on a lot.
W: For sure. I actually credit a lot of that to my publisher now, his name is JJ Corsini. He found me when I was eighteen, when I was an MC. “CVTVLYST” was actually part two to a song called “Genesis,” which is no longer on the internet, but I put that out for the fans. It was the same, just four minutes of straight bars. JJ discovered me off that. He was like, “Hey, you have an insane raw talent, but you need to go from being an MC to being a songwriter.”
A lot of that also came from playing with a live band. I played in a band in college called the Illaquips. So much of hip-hop and jazz and funk is just improvising, so we were doing a lot of freestyling, and in doing that, you come up with different melodies and different flows that you wouldn’t write just by writing. So that became part of my process.
11: And now you’re leaving more space for some of the production. I did want to talk about the production—the beats that you picked—because you’ve got a stable of incredible producers on If I May. How did you pick the beats?
W: I am extremely picky. This mixtape would not have taken this long if I were just taking the beats that were given to me and writing to every one of them. Beats are such a staple. I can’t rap over a whack beat. Luckily we were able to get in the room with some of the best producers ever, which I’m incredibly grateful for. We’ve had these beats for a couple years, and I’ve been very selective about what I’m taking. Some came from beat packs where we’d get a hundred beats and I would pick one. Some were through sessions. I comb through beats like a monster.
11: You’re pretty tight with Dame DOLLA. How did you connect with him?
W: Dame actually reached out to me after my second viral video, which was a worldstar post. We just started talking. We’d chat once a month, building our relationship with the intent to work together at some point, and then I had this song called “Buzzer,” and I was shouting him out at the end of it. I was like, “Hey, are you down to be in this video?” And he was like, “Yeah, I’ll roll up.” We kicked, he came to the shoot and helped us move props and brought his friends. We got to know them pretty well, and from there he was like, “Hey, whatever you need, I got you.”
I reached out to him about “The Thesis” last December. I was like, “Hey, we haven’t even started, we don’t even have the beat, but I want to put this on your radar.” He doesn’t make music during the season, but I told him, “I want to do this for the Portland scene, and to have someone like you cosign would mean a lot for the city,” and he was like, “Yeah I got you.” I reached out to him once during the playoffs, but after that, I hit him up just to say congrats on the contract. He just goes, “Yeah for sure, I just recorded the verse and sent it over, did you get it?” I was like, “You recorded the verse the same day they announced your max contract? That’s legendary.”
11: So “The Thesis” is named after the hip-hop showcase at Kelly’s Olympian. The crew you put together, were those mostly people that connected through that showcase? How did you put that lineup together?
W: The goal I had with the people I picked was to hit different areas of the city—different sounds and different generations. So to have people like Vursatyl, who’s been in the scene and helped build it since they ‘90s, and then to have Illmac—who’s this legendary battle rapper, who’s been putting on for St. Johns, who’s built a following of people who love him for his punchlines—and then Kayela, who’s the upcomer in the scene—to put all these people together with Dame, and say, “Hey, these people are here and this is a taste of what’s been happening in Portland from the 90’s until today.”
11: You had Riley Brown working on “The Thesis.” How did you link up with him?
W: Riley for “The Thesis” was a no-brainer for me. I think as much as “The Thesis” represents the passion and the heart of the hip-hop scene. Riley is also that. He’s brought a lot of people together, and has worked with pretty much everybody in the scene. He’s one of the hardest workers I know, and really cares about the growth of an industry culture here. I knew that I had to bring him in. I just had a vision where I wanted to put everyone in their location in the city and have everyone do their thing and be themselves.
11: I also wanted to talk about live shows. Have you been touring off this album at all?
W: No, I’m about to start.
11: And you’ve got your first show here on the 14th?
W: Yes, the 14th is my first headlining show in Portland. We’ve held off for a long time on that. We didn’t want my first moment here to be piggybacking off something else. We’re at the Hawthorne Theater, and we’ve actually partnered with Amazon for it. We’re gonna turn it into an incredible experience for the fans. We’re designing the space with the help of Camp Grizzly. It’s gonna be very cool. I just left my first rehearsal for that show.
11: Nice! What are you working with, personnel-wise? Do you have a live band or a DJ?
W: We have a DJ, DJ Fatboy, who’s a legend. We have Shook Black on the drums, and then we have Cary Miga, who’s playing bass, and then my Hype man Raph, who’s a breaker. He does background vocals. He’s just around, so it’ll be the five of us.
11: What else do you have coming up after the show on the 14th?
W: I’m on tour with Earthgang and Mick Jenkins starting January 16th in Seattle. It’s 30 dates and it’s my first tour. It’s the greatest people to tour with, so I’m stoked. Earthgang and JID are managed by the same people, and we know their team super well, so it worked out.
11: Are you back in Portland with that?
11: Beyond that, do you have plans for the next project?
W: Of course. We started making songs for the album when we started making songs for the mixtape. I’m going to hold off on my album for a little bit. We’re going to follow this up with probably a little EP, going to drop a couple singles hopefully while we’re on tour, and hopefully have an EP before the end of the summer. But don’t quote me on that. Everything always takes longer than you think.