In this weird, current era of hip-hop dictated by streams and social media, going viral can be a blessing. It can mean getting a leg up on the competition, getting your name out there while so many others languish in obscurity. It can be the difference between getting picked up and endorsed by major outlets and grinding out a few thousand YouTube views at a time, hoping to build an organic fanbase in a world where attention cycles are getting shorter by the day and more and more content fills the ether hoping to catch that dwindling supply of attention.
But going viral can also be a curse. It comes with expectations, assumptions, increased scrutiny, and even mistaken identity. That was the case for Portland rapper Wynne, who at 20 years old has gone viral not just once but twice. Both times, her freestyles so impressed viewers that numerous blogs picked up coverage of them and mistook her for Hailie Mathers, the daughter of Detroit rap legend Eminem — despite the fact that Hailie is four years older and looks nothing like Wynne, minus their characteristic blonde hair and blue eyes.
Wynne, who says she really doesn’t “want to be the viral white girl,” is flattered by the attention, but in something of an anachronistic relationship with modern zeitgeist, would prefer to build a grassroots following the old-fashioned way. She has leveraged the close-knit culture of her hometown’s hip-hop scene to cultivate a strong local following, and a chance meeting with Dreamville’s JID led to “Ego Check,” a lyrically gymnastic display of the duo’s verbal prowess that proved that Wynne could hang with some of the best.
On her independently-produced 2019 debut album, …If I May, Wynne’s skills take the forefront as songs like “Roll Call” address the elephant in the room when it comes to issues of white privilege in a Black culture such as hip-hop. Other highlights include “The Thesis” a Portland-centric posse cut that gets a boost in star power from Trail Blazers guard Damian Lillard as his rapping alter ego Dame D.O.L.L.A., and “Ken Mastrogiovani,” an improvisational track named for the drummer who freestyles an unconventional beat that Wynne has no trouble dancing over with scintillating wordplay and impeccable cadence.
The album’s warm reception among fans, as well as Wynne’s previous connection with Dreamville through JID, led to her becoming the opening act on Earthgang’s Welcome To Mirrorland tour along with new Spillage Village member Jurdan Bryant and Mick Jenkins. Their stop at the Fonda Theatre in Hollywood is where we connected for an in-depth interview that speaks eloquently to the current moment, despite taking place before 2020’s pandemic quarantine and civil uprising. Call it prescience, call it good fortune, or attribute it to the frustrating cycle of national indifference to the very real social cancer of systemic racism, but when Wynne talks about the need for white allies to tackle injustice alongside the oppressed, her words ring as true now as they did when tours were still a thing.
I don’t necessarily see a lot of young artists your age, who have your particular independent hustle and vibe and that ingenuity and that tenacity to just stick to it. Where does that come from?
I don’t know. I have great parents who work really hard and they instilled a lot of incredible qualities in me and my siblings about hard work and perseverance. And it was the kind of family that if you join a sport and you don’t like it, it sucks because you’re now on this team for two years.
That was their thing. So I took a lot of that. And really, I just, I was lucky enough to figure out what I wanted to do when I was 12. And I was like, damn, I’m going to lock myself in my room and I’m going to make this happen. I don’t think it’s very common that you know so early. And I think that helped me get a leg up because I spent all of college, all of high school, just studying and listening and looking and just trying to understand.
That’s crazy you say 12 because that is young. And also, not to down your hometown or anything, but like…
That’s a great question. So I’m from a suburb called Lake Oswego and it’s the whitest suburb you can imagine. And my older brother actually introduced hip-hop to me when I was nine. We just shared an iTunes account so I had all of his music. And I was asking him for recommendations and he played a lot of the Aftermath stuff at the time. This is like 2006, 2007. And so I just was listening to everything. He was on a lot of Lupe, Kanye, Jay-Z, 50, Eminem, and taught myself by learning to rap along with them. And then when I was 12 and I was in middle school was when I started writing music and I was like, shit, I think I could do this. I think I could be good at this.
And I feel like hip-hop has kind of an outcast art form and I very much was an outcast in my community. I’m not super social. I’m not about bougieness or glamor or anything. And my suburb is very much that way. So I was just to myself and found solace in my favorite MCs and really just fell in love with the way people could put words together and was fascinated by it. It was like a puzzle.
And it’s actually funny that you mention being an outcast and also mentioned Eminem because those are the two people who I think you draw the most comparisons to: Eminem and Iggy Azalea, who both talk about not fitting in and finding solace in rap. Why do you think people are so invested in connecting you specifically to people just because you look a certain way? Do you think that holds you back in any kind of way?
No. I think it’s, honestly, I think it’s fair. How many times do white people see one Black person and they’re like, “They must all be this way?” I spent a long time when I was younger wrestling with the idea of “am I going to be accepted?” and really just came to learn that if you’re authentic and you’re yourself, people will accept you. If you try to be fake, then they won’t accept you. And I think people like what’s familiar to them. So they see a white girl rapping and they think Eminem. Obviously I’ve taken influence from Eminem so it’s just an easy comparison. It didn’t help that I went viral as his daughter a year ago. That’s been a process.
It happened twice. I was offended on your behalf. Did these guys do any basic research where they just started throwing stuff out there?
No, it was a trip.
Going back to you pointing out that a lot of people will make a judgment based on a bias and prejudice, I noticed that very early on in your album you get that right out of the way. You just establish right out of the way, “I have a voice and a platform. This is what I intend to do with it.” Why was it so important for you to throw that line in there?
I basically went to college for studying social justice issues. So I spent a lot of time in political science and ethnic studies and women and gender studies courses, just trying to understand my place in the world and what that means. Especially as a person who participates in hip-hop, you just need to know your shit. That’s a huge reason why it exists: so people have a voice. And I think it’s super important for… I guess what I’ll say is the oppressed will not stop being oppressed until the oppressor realizes they’re oppressing.
The more white people talk about it, the more, hopefully other white people can recognize it. Especially because so much of my fan base is going to be white people. And I can’t fix all of them. I can’t have one-on-one conversations about this is what this means, but I can at least spark a thought. It’s going to take a lot of those sparks, but as many as I can put, I think that’s important. I have a lot of people come up to me like, “Hey, you’re opening a door for other white women to be rappers and that’s really dope.” And I’m like, okay, but…
That’s not the goal.
I’ve never set out to open a door for white women to be rappers. If white people are going to participate in hip-hop, they just need to know their shit. And so I just want to help set that standard that if there are going to be people after me, cool, but this is how I did it. So if I eventually get to a place, 10 years, where I can reach legendary status, hopefully there’s a blueprint of “know your shit.”
That’s actually funny because on the show that we do, People’s Party, El-P came on and said, “You can’t have love for the culture without having a love for the people.”
That’s huge.
A thing that I thought that you did on the album was very smart was the interlude where you immediately throw a lampshade on everything anybody can say about you.
Exactly. And the reality of it is I really don’t fit many of those stereotypes, but people think I do.
I was sitting there co-writing jokes. There’s a lot of sides to who I am that are very helpful because I can go viral. I’m clickbait. When I walk out there between Jurdan Bryant, Mick Jenkins, and EarthGang, people pay attention to me because it looks weird. It looks out of place, but it’s also, we need to get some shit out of the way first. If we’re going to get to this point and you’re going to respect me, let’s just throw this… You have to be able to make fun of yourself. I’ve known Cipha Sounds for a while. He was one of the first people to find me in 2016. And he does a lot of comedy stuff now and tours with Dave Chappelle and Michael Che. And I just knew that I wanted him to roast me. So I called him up and he was like, “Hell yeah, I’ll come roast your ass.”
It’s funny because I basically write articles all the time where I speak to these issues with white fans in hip-hop. It leads to some really angry comments and awkward moments in real life, but it feels necessary.
And it’s like let’s talk about it because when people say they’re colorblind… you can’t be colorblind because then you’re ignoring all of the differences between people that cause certain people to be oppressed and certain people to be uplifted. So it’s like let’s talk about these things and about how different I am, because I’m super different and that’s a huge deal. I didn’t fucking grow up like this. I don’t face these kinds of oppression, but I’m still participating in the music that is a reflection of those things. So let’s talk about what that means.
If you had to give somebody the Hollywood logline of what the album is about, what do you tell them? What’s the elevator pitch of your album?
It’s basically me giving myself permission to be a little bit dumb.
Because like I said, I really spent my… up until I was 20 locked in my room, learning how to rap. And then I was 20 and I was like, “Shit, I should be a college student.” So I did that and I turned up and I made all these fun memories and I came to LA and I went to some stupid parties. I went to some really sick ones. You have to go through shit to tell the stories. And so this was me letting myself come a little bit out of my shell and then tell those stories.
What are some of the drawbacks of doing it independently and what are some of the advantages?
Is actually, it’s really interesting because I’m not signed to a label, but I wouldn’t consider myself independent. I have a distribution deal. So I’ve had a little bit of funding for the project, but mostly just I have an incredible team who was able to connect me with a lot of incredible people. So it’s like I’m working with my idols. I’m working with Sounwave and Hit-Boy and Christo, all these incredible people, but I’m still a nobody. So I’m stoked. But it comes out and it takes time for people to discover it so the downfall is, we don’t have a shitload of money to just throw into marketing and publicity. And it’s hard because you spend so much time making this incredible body of work. To you, it’s the most important thing you’ve ever done. And that’s anything in the music business these days. It’s something’s hot for a week.
And so a huge goal of this project, between me and my engineer, Itay, who is also my tour manager, was to make a project that felt timeless. Something that maybe could have come out in 1997. And it maybe could have come out in 2019. Because instrumentation doesn’t get old. A fad does. Specific programmed 808s do. But when you have… it does something to your brain when you hear an acoustic guitar. It does something to your brain when you hear a drum loop that was recorded live. And that kind of thing, it makes it easier to put out a project independently because someone can discover it, in six months it’ll still be relevant. Someone can discover it in two years, it’ll still feel relevant. And it’s fun to grow day by day. It was overwhelming when we were going viral. I didn’t like that.
What you’re talking about as far as songs having to sit for a little while and build, when you think about Lizzo had “Truth Hurts” out for two years and nobody cared about Lizzo. Doja Cat had Amala, which is an incredible album but nobody cared. “Mooo!” comes out and suddenly everybody’s like, “Who’s this Doja Cat girl?” What’s the process or what was the conversation that was had around how we use this or do we decide not to use this?
I was very intentional about “I do not want to monetize this moment.” I always knew I was going to do this, but I didn’t know how it was going to happen, and I should have known it was going to be by going viral. And it did great things for me. It connected me with my team. It gave me incredible opportunities. It gave me a platform to be able to reach out to people. It was great. We sat with all the labels, but when we walked in, we said, “We’re not here to sign, but we just want to talk.” From there, they put you in a room with people and you can start negotiating, but it was just like, “I don’t want to be the viral white girl.”
I actually sat with a label who called themselves out because they brought me in because I went viral and I played my song, “An Open Letter to Donald Trump.” And the president of the label at the time starts tearing up. My publisher starts tearing up and I’m tearing up and they say to me, “We’re doing you an injustice because we brought you in here because you went viral and we sign however many acts a year for a couple hundred thousand dollars and then we get a hit out of them and that’s kind of it. And you’re not that.”
And that was huge for me because I’ve always known my worth. And I’ve always known there’s power in uniqueness. And I really didn’t want to capitalize on being the viral white girl that can freestyle on Twitter.
If I May… is out now. Get it here.