In the living room of Wynne’s tidy one-bedroom apartment, there is a glossy print photograph of her crouching defiantly behind two lions in a sepia-toned forest. The photo was taken on her family’s African safari vacation and reflects two sides of the 20-year-old rapper’s identity: a gutsy, fearless ambition and white and class privileges that afford certain work and vacation opportunities.
The photo hangs among other decorations emblematic of Sina Wynne Holwerda, the Portland rapper and University of Oregon junior from Lake Oswego who goes by her middle name. On one wall, a framed poster ranks rappers by the size of their musical vocabularies. An adjacent poster organizes rappers into a hip-hop periodic table of elements through sub-genres (pop-rap, gangsta, trap, etc.). A bookshelf balances an array of literature on hip-hop and politics alongside VHS cassette tapes and DVDs of Disney movies, and an intricate map of Disneyland covers a wall above a keyboard.
Here, Wynne relaxes on a crisp white couch and talks through every aspect of her identity (white, female, affluent, Oregonian) and ambition (successful hip-hop star) to arrive at her current moment of career limbo—or “purgatory,” as her music engineer Itay “Ty” Lerner calls it.
Although Wynne hasn’t released original music in over a year, her starpower has been growing. It has been seven months since a video of Wynne rapping went viral online with over 3.5 million views. The video led to accolades and connections from record labels, Grammy-winning producers and hip-hop big shots, not to mention loyal fans across social media: she has 75,000 followers on Instagram, 43,000 on Twitter and 35,000 on Facebook. She put out a remix of Lil Pump’s “Gucci Gang” on Soundcloud in early March, and a remix of Jaden Smith’s “Batman” on April 2. Soon, when she’s ready, she’ll “push the button” and release the stockpiled music she has created over the past year with Ty and a select mix of famous and up-and-coming producers in Los Angeles, Portland and Eugene.
To some, the blonde, blue eye-eyed, white girl rapper is an uncomfortable anomaly in an art form created primarily by and for black culture. As a woman, she is scrutinized through the misogynistic lens of the industry and genre. When she and Ty walk into a business meeting, the all-male attendees assume Ty is the artist and don’t acknowledge Wynne. I ask how that feels. She tips her head back, ponders the question for a beat, then says through a slight smile:
“Like revenge is coming.”

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On a night that culminates at Sprout City recording studio in Eugene, Wynne dons a baseball cap with the word “Captain” in bold lettering across the front.
We grab her hype man Rafael “Raf” Newman, a 21-year-old self-described “hip-hop kid” from Seattle, from his house and drive to Voodoo Doughnuts downtown to catch about 20 minutes of their friend Spencer Smyth in a rap show. After a little while, Wynne says it’s time to leave. The plan tonight is to track Raf’s vocals for a new song. Raf wears jeans and an oversized jacket  reminiscent of a 90’s Fresh Prince of Bel-Air style. He floats around the room saying bye to their acquaintances. Wynne waits near the door and checks her phone.
In the car, Raf controls the aux cord and plays a few soul-tinged songs by hip-hop group Young Bull that I save to my Spotify library.
We get to the studio around 10 p.m. and meet Ty, a 22-year-old music technology-major graduate of UO and Wynne’s right-hand man. They talk about their recording goal for the session. Wynne says Raf’s old-school, R&B-style singing will layer well on this new song. She wrote it in 10 minutes (sometimes a song comes to her all at once.)
It starts with a verse from a masculine persona who knows exactly what to say to get a girl to melt, then it fades to a catchy hook: “I’m a playa, playa, playa, yeah.” In the second verse, Wynne switches to a female “playa” perspective who sees through a boy’s phony charms, but indulges them anyway for her own objectives.
Wynne interprets: “The female version of the player is like, ‘I know what you’re doing, but I want free drinks and I want things that you’re gonna give me if you believe that I believe what you’re saying.”
Wynne and Raf take turns singing over specific parts of the song in the recording booth—sometimes they make up vocals on the fly, but usually they’re hitting a specific, pre-planned harmony or rhythm. At one point, Raf jazzily deviates from Wynne’s vocal instructions, then pokes his head out the booth to gauge her opinion.
“Less runs, more sticking to the script,” she says with a straight face that cracks into a grin after Raf rolls his eyes and shuts the door again. Wynne said earlier that she wore the “Captain” hat because she would be the boss.  
When the energy sags around midnight, Wynne tells Ty to play a few of the duo’s finished songs that they are waiting to release. One is produced by Los Angeles up-and-comer Jonah Christian. A music composer for Beats 1 on Apple Music, Christian has worked with Anderson .Paak and Portland rapper Aminé. Someone with a production credit on the Black Panther soundtrack, and who has worked with Kendrick Lamar, produced another track. Wynne doesn’t want to name that producer yet.
As we listen, Raf bobs his head and dances. Wynne matches her hype man’s energy, alternating between rapping along to herself with surgical precision, and full-body vibing to each track. Ty jumps with the rhythm, and throws his hands over his face in a sort of tormented delight. He yells about wanting to release new music. Over the past year, Wynne and Ty have worked to sharpen all aspects of their craft, from singing and variety in rap flow to every minutiae of recording and mixing.

Ty says these tracks break new ground.
“As far as lyricism, cadence, flow, presence on the mic, thoughtfulness, the concepts and the execution of every single syllable—it’s some of the most technically advanced and well-executed rap music ever made,” Ty tells me.
Ty admits he’s just a white kid from Oregon, but asserts that industry “gatekeepers of the culture” are similarly impressed with their work.
Wynne laughs at his description. Her take is more humble. “I’m excited to see how people react to it,” she says. “I want to get to where the technical skill is undeniable. That’s where Eminem had to get to, where it was like, ‘You can say whatever you want about what I look like, but you can’t deny my rapping ability.’ That’s the level I’m about to get to.”

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Wynne grew up in Lake Oswego, an affluent suburb of Portland. Her mother, Kasey Holwerda, has a law degree but does not currently work. She is married to Wynne’s father Steve Holwerda, a chief operating officer of a capital management company. Wynne began rapping at 9 after her older brother introduced her to hip-hop.
“I learned how to do what I do from listening to Eminem, which is such a common white thing to say,” she says. “He taught me to flow.”
She consumed and practiced rap music by digesting the catalogues of artists from Jay-Z to J. Cole. She gained enunciation skills by rapping along to their songs, and started writing her own material at 12. That’s when she knew she wanted to be a rapper. At first, Wynne was shy about her ambition, quietly refining her skills in her bedroom. Then in eighth grade, she performed an original song at her school’s talent show. The audience, which included her parents, was shocked.
“People were surprised because she’d never done that,” Kasey says. “Nobody knew she had this secret talent.”
Growing up in Lake Oswego, where less than one percent of the population is black, Wynne saw constant reminders of the privilege she and her community shared. Her peers often used the “N” word while reciting rap lyrics, but she didn’t. Lots of people listened to hip-hop, the lyrics so different than their everyday lived experiences. For Wynne, it was more than just party music. Hip-hop provided an opportunity to learn about black politics and black culture, she says.  It gave her insight into her own privileges and the oppression of black America.
“If I wanted to do this with my life, I needed to respect it,” she says. “I spent junior high and high school reading hip-hop history books and listening to everyone I could find.”
Race will forever be a point of contention in Wynne’s career. And justly so. She is an attractive white girl building her career in black culture. Wynne belongs to a group of white rappers like Eminem and Iggy Azalea who adopt the style and vocal cadence of black musicians as part of their own artistry.
Loren Kajikawa, assistant professor of ethnomusicology and musicology at the UO, lays out three criteria by which white rappers are usually judged in hip-hop: skill, how they benefit from privilege, and political commitments to black culture. Kajikawa teaches a class on hip-hop music, culture, history and aesthetics at UO, and has had Wynne as a student in a number of classes since fall 2015.
To illustrate these points, he describes how hip-hop had different reactions to Iggy Azalea and Eminem. From the get-go, Iggy had skills, but the Deep South accent she used in music contrasted with her natural Australian affectation—some accused her of appropriating black culture. As Iggy’s popularity grew, her white privilege was scrutinized. But Iggy was defensive.
“Her attitude was, ‘Screw you, I’m doing me,’” Kajikawa says.
Iggy didn’t comment on what was happening in black America during her ascent to fame—the shooting of Michael Brown by Ferguson police, and the inception of Black Lives Matter. Prominent rappers like Q-Tip and Azealia Banks called her out.
“To be a white female rapper in that political climate and not speak about white privilege, or what your participation in the art form means, or what’s happening in the world doesn’t seem right,” Kajikawa says.
Eminem had a different reception. His skill was formidable, and he grew up in a predominantly black neighborhood. He acknowledges and uses his white privilege to fight for and bring attention to issues of black America. In of other aspects of his life, Eminem is problematic, to be sure. But he understands he is a guest in black culture.
Sexism may have also played a role in Iggy’s quick cancellation compared to Eminem’s sustained popularity. Kajikawa points out that misogyny in hip-hop (as in many music genres) likely intensifies criticisms of Iggy. Non-male rappers like Iggy and Wynne are automatic outsiders because of their gender, and to some, women rappers are seen as inauthentic.

Perceived authenticity in hip-hop can also sometimes be tied to adversity. Eminem grew up in poverty and abuse. Snoop Dogg was on trial for murder when he got big. 50 Cent was shot nine times before his music career.
But to Kajikawa, good hip-hop does not need to be born from adversity.
“It’s a disservice to artists, even those that have struggled, to equate struggle with art,” he says. “Going through bad shit doesn’t produce good music. It’s messed up if you think about it because it takes away the creativity, hard work and genius of artists.”
Wynne can’t rap about adversity how Eminem, 50 Cent and Snoop Dogg can. But she could make music to inspire people; to help her audience to cope, to feel seen and heard.
“That question about struggle will be answered by her art,” Kajikawa says. “Does the music convince people, even though she’s from Lake Oswego and hasn’t experienced struggles that they have, that they can identity with her?”
Wynne’s use of black music aesthetics and her own white privilege make her wonder: is she plucking opportunities from black artists? Would she be getting the same level of attention if she were black?
These are all questions she has considered throughout her career, things she mulls over in music and ethnic studies classes at UO—things she brings up unprompted at our first meeting in Lillis Cafe.
“I’ve had a struggle in my life to decide, am I hurting this culture by participating in it? Or can I help?” she says. “I always felt like, if you love something, let it go. I know what people are going to say about me. I can never say, ‘You’re wrong!’ because I know what this looks like. I know what it is.”
In her studies as a popular music major, she grapples with the history of white people appropriating black music in America: first jazz, then rock, and now hip-hop.
“I understand it, and because I chose to pursue it and participate in it, the thing that I can do is bring the message of what I’m against,” she says.
What is she against? President Donald Trump, to start.
The last song she released in January 2017 was “An Open Letter to Donald Trump,” a scorching manifesto recounting America’s systemic history of racism, sexism and socioeconomic inequality which culminated in Trump’s election. It was inspired by a call on Christmas Eve 2016 from Kenny Burns, the senior vice president of marketing for rapper P. Diddy’s entrepreneurial business venture Combs Enterprises.
“This is your time,” Burns told her. “There’s a reason that everything is happening around you right now, and there’s a reason why the people I know have started talking about you. It’s because Donald Trump is about to become president and you have the skill and white privilege to talk about it.”
It felt like the scene in Lion King where Mufasa speaks down at Simba from the sky.
“It was the trippiest phone call I’ve ever had,” she says. “We chatted for an hour about privilege and what to do with it.”
Burns suggested writing a letter to the president to articulate her generation’s political frustration. She took his advice, then recorded the song with Ty at Sprout City. In the studio, they did several takes of the song in its entirety.
“You can’t break the energy of that song,” she says. “In the best take we got, I was bawling my eyes out. The lights were all off.”
Kajikawa says that in the best-case scenario, Wynne could use her privilege to support social justice efforts and make positive change. But at the same time, can she be an effective ally when she’s also a competitor?
“Nobody wants to hear a rapper say, ‘I’m the second best,’” Kajikawa says. “It goes with the territory that you’ve gotta promote yourself, believe in yourself, and project confidence that you deserve to be there. That you’re the best.”
Kajikawa says Wynne should also be careful navigating relationships with women rappers, especially black women. If she blows up, and especially if she gets recognition for working with famous black men rappers, she needs to stay humble and help bring black women rappers up. As a white women, it could seem like she’s receiving preferential attention from the industry and black men rappers. And at the same time, Wynne could be put in a “just women” box by working with only or mostly women.
There has yet to be a successful, white, female rapper who stays popular and hits all the benchmarks for acceptance in hip-hop. Wynne could blaze that trail, but she’ll be analyzed and picked apart from every angle. Like Iggy, her vocal cadence is criticized by some, though Kajikawa somewhat shrugs that off: “You could say she’s imitating black speech, but that’s what hip-hop is: a black oral tradition. That’s the musical language, and either you can do it or you can’t.”

Wynne’s whiteness sticks out from the tradition of hip-hop, but not in the Portland music scene. DJ Kylph, host of a weekly hip-hop radio show on Portland radio station KXRY 107.1, put this in perspective: living in Oregon as a black man, he says white people rapping is nothing new to him—but he thinks Wynne has remarkable talent and intellect.
Kylph, who helps curate a monthly hip-hop event in Portland called Mic Check, first discovered Wynne from a music video for her song “CVTVLYST” (pronounced “catalyst”). He describes her as a fierce rhymer who is soft-spoken in person.
“You’re gonna have naysayers,” Klyph says. “I would be remiss if I didn’t say there are people who look at the fact that maybe she’s getting some attention because she is a white girl. As a curator in this city, it’s a task of mine to weed out artists who are nice and artists who are nice. Wynne is in the latter category. She’s different.” 

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Wynne’s parents didn’t understand her drive to be a rapper until the past year or so. They never knew much about hip-hop. They played Motown in the house as she grew up. While supportive of her passion, they were skeptical of rapping as a career. She and her father, who she describes as careful and conservative, used to get in heated arguments about having a backup plan.
“I don’t believe in a plan B,” she says. “When you want to do something like this, you have to be crazy. If I had a plan B, that would be taking away time I need to put into this.”
Wynne’s mother Kasey Holwerda, who described the extent of her hip-hop knowledge before Wynne’s career as “the song ‘Baby Got Back,’” recounts how she came to understand her daughter’s talent. In 2016, she accompanied Wynne to an underground hip-hop showcase in Portland which Wynne was invited to perform at.
They stuck out, Kasey says, as the only mother-daughter pair among the “cool” performers in their 20s running through soundcheck. She observed them while Wynne practiced.
“Their jaws were on the floor,” she says. “That was when I realized, she’s better than most of these people. This is gonna be interesting.”
Wynne closed the show. When it was over, they drove home in the family minivan.
“Not many girls would let their mom drive them in a minivan to something like that!” Kasey says. “She’s who she is and makes no bones about it.”
Wynne occasionally performed and consistently wrote music throughout high school. In college, she found like-minded friends in a hip-hop dorm community. Her freshman year, she joined the Illaquips, a hip-hop collective originally named the UO Hip Hop Ensemble, and became close with fellow members Raf and Smyth. Wynne met Ty separately about a year ago.
Raf planned to audition for the group as a saxophone player, but in “typical Raf fashion,” Wynne says, forgot his instrument and switched to a freestyle emcee (rapper) audition. When an emcee freestyles, they rap to a beat completely on the spot. Jay-Z and Lil Wayne claim to never write down any of their lyrics—they only freestyle. This requires confidence and disposition to mistakes—Wynne, ever the perfectionist, had never freestyled before joining the Illaquips.
“I was solely a writer,” she says. “I didn’t have the guts to freestyle. You have to be willing to fail a lot.”
Over time, she got comfortable with freestyling thanks to Raf and Smyth. Her friends say she is now better at it than them. She aims to be at that Jay-Z/Lil Wayne level someday.
As we talk in her apartment, soft Frank Sinatra and the scent of a brown sugar and chestnut candle waft through the room. Muted hip-hop videos of Kendrick Lamar, Travis Scott and Jay-Z play on the TV—Wynne usually keeps a playlist of YouTube videos going on silent for constant creative inspiration.
She is especially attuned to her senses, she says, something Ty, Smyth and Raf all separately mention to me. Wynne says she has synesthesia, a neurological condition that causes different senses to crossover with one another. For her, and other musicians like Billy Joel and Pharrell, synesthesia manifests as feeling correlations between color and sound. For example, Wynne gravitates toward purples and blues in sound—one of her favorite feelings is driving into a tunnel with purple or blue music blasting through the car speakers right as the song dips into the darkest shade of the color.
The synesthesia also causes her to feel distinct parallels between music and other uber-specific, less tangible concepts. Ty is bewildered by it.
“I’ll be trying to make beats and she’ll be like, ‘No those drums sound like birds flying through a yellow sky and I want more drums that sound like a raptor running through a forest! You know what I mean?’,” he says wide-eyed. “I’m like, I have no clue what you mean!’”
Ty laughs, and recounts how, on the day they first met, Wynne sent him a photo of a poster of purple color splotches on her wall.
“She…had circled the purples she was more in tune with at the time,” he says, deadpan. “She’s still like that. I don’t understand it an inch more than I did that day, but it’s what makes her her.”
Wynne thinks her unique way of sensing the world has roots in her infatuation with Disney movies, mostly older animations like Peter Pan, The Lion King and The Little Mermaid.
“I probably have a Disney reference in every song,” she says. “The thing that inspires me about Disney is there’s so much detail in everything they do—all their songs, colors…nothing is left untouched. I want to approach my music, my artistry, my brand, the same way. I want every line to mean something. I want everything to have a punch.”

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The first of Wynne’s two viral videos was posted in August 2016. It got about 40,000 favorites and 20,000 retweets on Twitter, and was posted by Snoop Dogg to his Instagram. She says she “can’t even watch it anymore” though because she sounds too immature.
The reception of the second viral video, posted in August 2017, dwarfed the first. It arose during a period of uncertainty for Wynne and Ty—they had recently received an underwhelming reaction to some songs they shared with cherished industry connections. The duo thought the songs were mind-blowing; the industry heard nothing special.
Submerged in this inspiration hiatus, Wynne didn’t think much of the video. She made it on a whim, then sent it to Ty for feedback. In the video, just over a minute long, she navigates the beat of rapper 21 Savage’s “Bank Account” with smooth metaphors, punchlines, humor and even props (lipstick and a honey bottle) to complement her rapping.
Ty was with his girlfriend when he first saw it. He was so excited, he says, that he watched it four times and ran around the house. Over the phone, Ty told Wynne it would go “STUPID viral.” She didn’t believe him.
“When you watch that video from the perspective of someone who understands hip hop and lyricism, and the real science and art behind the language and manipulation—that level of execution was extraordinary,” Ty says.  
Wynne was alone at her family’s home in Lake Oswego when she posted it, first on Twitter and then Instagram. It took off on Instagram within 30 minutes, garnering hundreds of likes, views and shares per minute. Worldstar, a popular viral video social media group with 14 million Instagram followers, messaged her and asked if they could post it. She said yes—with credit—and it exploded.
Wynne stayed awake for hours watching the video’s engagement climb higher and higher. Refresh: ten thousand more views. Refresh: another thousand followers. Refresh: a famous producer followed her.  Refresh: a few record labels follow her. Refresh: a hundred new messages.
Ty was busy with friends in Eugene, Wynne’s parents and her publisher J.J. were both on vacation and Wynne was practically in isolation for the greatest moment of her career up to that point.
“I’m lucky because when I had gone viral the summer before, it was like a roller coaster,” she says. “When it happened the second time, I knew what it looked like.”
Wynne says she received overwhelmingly positive feedback on the video. She knows her looks played a major role in getting attention, which made the amount of responses to the actual music content so stunning.
“The biggest impact that it had for me was comments like, ‘this is what cultural appreciation looks like, not appropriation,’” she says. “That made me feel good because people saw that I spent my time studying and working on the craft of lyricism.”

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Around September 2017, Wynne and Ty began attending regular meetings with record labels and Grammy award-winning producers. She says their main takeaway from the industry experience is that they don’t need to jump at the first exciting offers coming their way.
Wynne and Ty recently met with Scott Storch, a one-time giant in the industry who has produced for Beyoncé, 50 Cent and Dr. Dre (he did the song “Still D.R.E.”). Storch made a career comeback after overcoming cocaine addiction. Meeting him, they say, was unbelievable.
In Wynne and Ty’s madcap recounting, they take an Uber to Storch’s mansion, about an hour outside of Los Angeles. Wynne is nervous because she had lost her voice performing a week before and can’t speak at the meeting. But she is too excited to cancel it. They arrive, step from the car, and are immediately hit with the smell of marijuana. They hike up a long driveway to a massive, Game of Thrones-esque door and text Storch’s manager to announce their arrival.
After 30 minutes, a man opens the door. Inside, they are greeted by a towering mural of Storch, six Chihuahuas, a Pitbull and the producer’s posse of nearly 20 people. One of them is Storch’s manager, Steve Lobel, a hip-hop music consultant who has worked with the Wu Tang Clan.
As they’re led through the house, they pass by Storch’s plaques and awards from work with Beyoncé and Eminem, a gigantic pool table, a bunch of tiny Storch bobbleheads, all of it seen through more marijuana smoke—“it’s like clouds, you can see clouds,” Wynne recalls—and arrive at a bar.
“Scott’s sitting in this little chair behind the bar looking like fucking Scott Storch: full orange sweatsuit, big aviators with some Cartier frames, and smoking a big-ass joint,” Ty says.
Storch’s posse is posted around him eating Domino’s pizza.
They introduce themselves then head to Storch’s in-home studio. The posse follows. In the studio, they hang out and play each other’s music. Storch and the posse smoke weed; Ty partakes, Wynne doesn’t. Lobel asks Wynne to articulate their vision, and since Wynne can’t speak above a whisper, she looks at Ty to answer.
“I’m high as fuck and I’m suddenly explaining our vision literally to my idols,” he says. “I didn’t know what the fuck I was talking about.”
“He was so confused,” Wynne says through a laugh. She still gives him a hard time for it.
While she is stoked about her brushes with fame, Wynne is intimately aware of the musical and social maneuvers that lie ahead in her music pursuits.
“There are a lot of eyes on me that I never thought would be on me right now and that’s why I’m taking so much time getting myself ready for what we’re about to do,” Wynne says. “I’ve known who I am as a person my whole life. But figuring out who you are as an artist is about translating your soul and putting it into a tangible form.”  
Wynne’s mom is impressed by her daughter’s deliberative, sensible approach to her career. Kasey recalls one extraordinary conversation they had in Portland the night before Wynne left for an important L.A. meeting.
“I feel like I’m a single mother,” Wynne told Kasey, “and my career is my child and I’ve raised this child alone since I was 12. I’ve done a good job, my child is an excellent child, and now all of these stepfathers are coming around. They want to help me raise my child and I just feel like saying to them: what can you bring to the table that I can’t provide?”
Kasey was taken aback.
“This is where Sina’s meant to be,” she says. “We support her 100 percent.”

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Unsolicited pictures of penises arrive regularly to Wynne’s social media inboxes—she used to get them daily on Snapchat, but she set her account to private to stem the flow. These pictures, sent by people who likely identity as fans, represent larger realities of sexualization and misogyny faced by women rappers.
Wynne says she works as hard if not harder than her male counterparts to get recognition, and even so, praise is inevitably tied to her gender: “she’s good for a woman” is a backhanded compliment she hears often.  
“I have had full mental breakdowns about this comment,” Wynne says. On this topic, her demeanor evolves from relaxed to agitated to defiant.
“What do you mean I’m good for a girl? I’m good period. You’re gonna tell me that I can spend ten years working on my craft and I’ll still only be good for a girl? What can I do to show you that I’m as good as these guys? That I’m better than some of them?”
She launches into a diatribe against the patriarchal music industry. Women are pitted against each other, she says, and the industry forces a mentality that only one female rapper (if that) can be successful at a time. She hears stories of record labels passing on signing women rappers because they “already have one.” She grapples with supporting an art form that degrades women.
“It’s like having an abusive lover,” Wynne explains. “I love this thing but it’s bad for me, it’s bad for women, and that’s hard to justify. My idol was Eminem, but he beat his wife. Can I separate the artist from their actions? Not really.”
Kajikawa echoes her sentiments.
“It’s so hard for female rappers,” he says. “It’s nasty, like, ‘There’s only room for one of us up here.’ Hopefully we get beyond that. We could have Wynnes and Cardi Bs and other people who deserve attention. How you get there is the challenge.”
In the studio, surrounded by men, Wynne often feels compelled to act “tomboyish” because of the dominating masculine energy. They’ll touch her differently, and go out of their way to hug her when it’s inappropriate. It’s uncomfortable, having to tone down your opinions and personality to be taken seriously in that environment. She describes a candid, backstage interview where Nicki Minaj sums up double standards for rappers of different genders.
“When I am assertive, I’m a bitch,” Nicki says in the video. “When a man is assertive, he’s a boss. He bossed up! No negative connotation behind bossed up, but lots of negative connotation behind being a bitch.”
Women aren’t allowed to do what men do, Wynne says. She gestures to the TV where a muted, braggadocious Kendrick Lamar dances in his “Humble” music video. She asks if I’ve ever seen a woman do a video like that.
Wynne remains optimistic that the industry is moving toward allowing more women rappers simultaneous success.
“There are a lot of battles to be fought but I think it’s the perfect time,” she says. “If there has ever been a time for a female rapper to just come out and do what the guys do, it’s right now.

Gallery • 7 Photos

Wynne does not have a record deal or manager, but she signed a publishing contract with a man named J.J. Corsini in September 2017. As her publisher, Corsini handles anything in her career that deals with money—like, making sure she gets paid by online streaming services. He is a crucial industry lifeline and mentor for Wynne and Ty.