Wynne took the first step toward moving past viral notoriety into a full-fledged rap career by dropping her debut mixtape If I May in October. The 11-track project came armed with plenty of firepower as some of the top producers in Hip Hop laced her with beats for her inaugural release.
Respected names such as Hit-Boy, DJ Dahi, Thelonious Martin, Jahaan Sweet and Theory Hazit were among the notable artists assembled for Wynne’s debut. But she credits her work with Top Dawg Entertainment stalwart Sounwave, who collaborated with her on the tape’s closer “212,” for guiding the direction of the entire project as well as what’s to come in the future.
In the second half of RealStreetRadio’s two-part interview with Wynne, the Portland-based MC breaks down multiple tracks from her If I May tape and explains why she views it as a coming-of-age project. She also shares how she linked up with J.I.D, The Internet’s Syd and an impressive lineup of producers for her first release despite being an independent artist.
RealStreetRadio: As a fan of lyricism and a lyricist yourself, I’ve got to imagine working with J.I.D on “Ego Check” was a special moment on the mixtape. Tell me a little bit about how that collaboration came to be.
Wynne: Our teams just kind of know each other, and I’ve been a fan of him for so long. He came on tour to Eugene where I was going to school in January. And so we linked up and I told him I was working on a project. I played him a couple of the records. And he said he was down to hop on “Ego Check,” and I’m just grateful it happened.
He’s the busiest man in the world right now coming off the back of that [Revenge Of The] Dreamers album. So, it was definitely a dream. He’s an incredibly skilled lyricist and he’s just so unique. He’s carving his own lane with the inflections in his voice and the way he flows and the words he chooses. So having him on there was definitely an honor.
RealStreetRadio: Nice. Another notable collab on there was Syd’s writing credit on “Petty.” How did that connection happen? And did you want her to do vocals too or did it work out best to have her strictly writing?
Wynne: That connection actually came through Jahaan Sweet, who produced that record. And that’s actually the oldest record on the project. We made that about three years ago now or maybe two. So, I had a session with Jahaan. It was actually a very strange session because I had completely lost my voice and could not talk at all.
We got connected and started playing through things and he played that record. Syd was on there with the hook. And I was like, “Hey, I think I can kill this.” And he was like, “Word?” And I was like, “Yeah, I think I can.” And he sent it to me and we made the record. Syd approved; she fucked with it.
I’m obsessed with that record as it was like the … Unfortunately, I manifested that situation after I wrote the song. So, I definitely have a salty spot for it, but it’s definitely a jam.
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I really can’t put into words what it means to see the insane reception of IIM. these were some of the best times of our lives and also some of the most confusing/hard. I’ll always cherish the hungover drives from Eugene to Portland, and the nights that made those drives more unbearable lol. holy shit- my TEAM. thank you guys for trusting me, checking me, and doing everything in your power to help me create. I cannot believe how blessed I am to work with you all. and to the fans- these songs are my stories, and now they’re yours too. go create your own memories with them, let them comfort you or push you. whatever you need. TELL A FRIEND: iF i MAY.. is out now. let me know your favorites. 🍯💛
RealStreetRadio: Just looking through the production credits, it’s kind of amazing to see some of the names that you were able to connect with on here. Can you just tell me about doing that as an independent artist? How do you foster these relationships and be able to assemble such a talented lineup?
Wynne: Yeah, oh my gosh. I mean never in a million years did I think that I would be in a position to work with my favorite producers on my debut mixtape. That’s just absolutely absurd. I have a lot of really great team members who have good relationships. And all they do is send a song and they’re like, “Hey, what do you think of this?” And from there, it’s me in the room with that producer and can we make magic. Do we click? Is this the relationship that we can build? And luckily the answer kept being yes.
The session I had with Sounwave was probably one of the most special sessions I’ve ever had in my life. I never really was writing in the room, and Sounwave’s one of my Top 3 of all time. Something just kind of came over me. I wrote some verses that ended up kind of crafting what the sound for the project was going to be and what the sound moving forward [for] the following projects will be conceptually.
And that just kind of changed my perspective on how to approach sessions, honestly. Just working with someone who’s such a dope … just the energy in that room. And same for Hit-Boy, we sat down with Hit and he played 30, 40 beats. And some of them, like the one that I picked that beat for “Rose City,” it just sounds legendary. It sounds something like something you would hear JAY-Z rapping over on Blueprint or something. It’s just classic.
I can’t even explain how lucky I feel to have those people being willing to contribute because like you said, I am independent. We have no funding, so for them to be down to be a part of it and just kind of offer it with love and just wanting to build with a new artist that they believe in, it’s just like I wake up every day thinking about that.
RealStreetRadio: That’s dope. I really enjoyed the skit you did with Cipha Sounds. Do you feel like being a white female MC, it’s best to just attack the perceptions head-on and try to have fun with it?
Wynne: Definitely. I learned that from my dad, Eminem. [Laughs]
Cipha was one of the first people to find me a couple of years ago, and we just built a relationship. He’s like my funny uncle; he’s always cracking jokes. He does a lot of comedy stuff now with Dave Chappelle and Michael Che, so it was just a no brainer to bring him in and have him just absolutely roast me. It was so funny.
We just sat in the studio for a couple hours and just freestyled some jokes. He laid it down in a couple of takes. And I mean I was on the floor when he said something like, “Me and my four friends got eight legs like a tarantula.” I was like, “What does that mean?” First of all, that’s bad math, you would have 10 legs!” It was so funny. Yeah, he killed that.
RealStreetRadio: One of my favorite records on this was “Playa,” which had a unique approach to it. Was it something where you wanted to let it be ambiguous and up to the listener’s interpretation? Or were you coming at it from two different perspectives?
Wynne: Yeah, I wanted to leave it open to interpretation because I like when people can have a conversation. But I am rapping from two different perspectives on there. From the guy in the first verse and from myself in the second verse.
That actually is a fun record for me because I freestyled that whole record. And it was one of the first ones that I made for the project and I knew that I wanted to put it out, but people weren’t really fucking with it. My team wasn’t really a big fan. It took a lot of convincing on my end. We did a lot of versions of the song, retracked the vocals quite a bit, just to get the vibe right. Especially over the two years since I’ve made it, just my voice maturing and learning that I can sing and figuring that out.
It was produced by Trox, who’s from Portland. Ty, my engineer, and I did a lot of additional production for it. Brought in a guitar and bass player, Ian, to add some flavor to it. It went through a lot of lives, and at the end of the day, it’s been a fan favorite. So, it taught me to trust myself quite a bit because I always believed in that record. I knew that I wanted it to be on the first project. So, I’m really glad that people have been fucking with it. It’s definitely a favorite.
RealStreetRadio: One of the best cuts is the closer, “212.” It was very relatable hearing about your curiosity and feeling like an old soul. Can you tell me a little bit about the inspiration for that track and the story behind it?
Wynne: So, 212 degrees is the boiling point of water and the verses in that and the hook are very much my boiling point. Because when you’re in your early 20s you’re going through a lot of changes. You’re figuring out who your real friends are, what you’re trying to do with your life, what your purpose is. You’re really just trying to find yourself.
And in the middle of going through all of that I’m having these bursts of meeting my idols and doing my first red carpet and going to parties that I have no business being in. But then coming home and doing my midterms and my family is going through things and my friends are going through things. And so it’s really just kind of like a … it feels a little bit like a coming-of-age song.
I wanted to talk about — as rapidly as I felt like I was going through it — all of those subjects within two verses. And those things range from in the first verse, I talk about in high school. Like I said, I’m from the suburb Lake Oswego. There was a lot of appropriation happening. And I think my favorite line on the whole project is, “I needed to know what happened to Rodney King/My classmates were getting low to apple bottom jeans.”
That as a concept — like I’m in middle school and in high school and I’m listening to Lupe, I’m listening to Nas. I’m hearing these stories and I’m doing my research. I’m reading books by KRS-One, trying to find the lineage of these stories and what’s happening in the world that I don’t know about inside the bubble that is my world. And my friends are over there — or not even my friends, just the community that’s around me — out blasting Hip Hop music and having no idea what is really going on in the world.
Just the poetry between those two lines and the concept of like … even in Portland, there’s a pretty intense history with Portland police and the Hip Hop scene in the city. That’s not my story to tell because I wasn’t around for it. But I gotta touch on how much easier it is for me as a white person to get booked for events and to get that recognition.
Meanwhile, the people in the city who have been doing it for decades are getting their shows shut down. And I can’t get in touch with my sister and I’m on a plane. And then one of my best friends in the whole world, her daughter was born and I’m not there to see it because I’m traveling. And I’m sleeping with different dudes that I’m meeting at bars and then finding out that they know who I am. And it was weird, like some weird fanboy shit.
It was a weird couple of years. It was very much like being, I say it’s like being Hannah Montana and what that feels like. Meanwhile, I’m losing touch with reality a little bit because my friends can’t relate to what I’m doing with my life. It’s a very different worlds than they live in.
So, you have your team and yourself, and my team understands super well what it means to do what I’m doing. And my best friend, Ty, knows exactly what it means to do what I’m doing and is here for me through everything. But still, it’s different to be the artist. It’s different to feel that kind of pressure and to get those viral moments and have all these people see a one minute clip of you and judge you off of it.
To give the world a body of work and let them judge you, it’s just a lot. And so it was weird to go through already feeling this distance happening between my friends and I, just based off my career, but also based on the fact that we’re all in our early 20s. And that kind of stuff happens naturally anyway. It’s just being kind of accelerated through speeding up. But you want to keep those people close because that’s everything. So “212” is kind of a culmination of all those things. And the tagline in that is, “I don’t ask God anymore, I just follow her lead.”
This was the first song I had with Sounwave where that song kind of triggered a thought in me that will inspire the future music that I make. And the hook just being like, there was a time where I was so depressed and suicidal in high school, that I was like, “Yo, am I ever going to be able to do this? Am I going to be able to be a rapper? Is this ever going to happen? Am I just chasing something that’s not going to work out?” And saying to the universe, “Yo, help me out. I need an answer, I can’t do this anymore.” And then coming to terms with, in my later years, it’s not my place to ask that question. I just need to do what I’m doing and take care of the people around me and follow what I think is true.
RealStreetRadio: It seems like this is just the beginning of your story but releasing the mixtape has allowed you to allete some of the pressure off of your back now that it’s finally out there.
Wynne: Yeah, it’s almost like an added pressure because I took everything out of me and the people around me to the fulfill what this project became. And it’s definitely a weight off my shoulders in that it’s everything I’ve been living for the last nine months. So to put it out is definitely a weight off, but it’s an added pressure now with whatever comes from this. Even if nobody hears this project, the fact that there’s a project out is going to change what’s happening around me and change the way we move and the way we do things.
So, it’s the do it again business. I’m excited to follow it up, but I’m nervous because I’ve put so much time into it. I’m very proud of it. And I think it’s the best work that we could do.
RealStreetRadio: As far as those future plans go, do you have any kind of a tour in the work to support this? Or are you already back in the studio working on the follow-up?
Wynne: Man, we were working on the follow-up while we were working on the project! So, there’s always new music coming. And we’ll plan a tour as soon as it makes sense, but I’m definitely trying to get on the road in the spring of next year. And we’ll definitely play a little hometown show for Portland in the coming months for sure.
Read Part 1 of RealStreetRadio’s interview with Wynne here.