What do Lake Oswego and a Trail Blazer have in common?

Wynne (born Sina Holwerda) is a rapper from Portland. Lake Oswego, to be exact. She’s so good, in fact, that she earned the rumor of being Eminem’s daughter. (Untrue.)

And if that’s not enough to make you take notice, look who jumped on board to rap in her song, The Thesis.

  • Damian Lillard. Yes, that one – the Portland Trail Blazers’ point guard. Lillard had called Wynne “the next big thing in Portland hip-hop,” which, of course, she loved, because Lillard is also a rapper. He sings under the alter ego Dame D.O.L.L.A. (He’d previously had a walk-on part in her video, Buzzer.) For The Thesis, though, he belted it out. (His tweet: New video for a track I jumped on with @wynne and crew. The Thesis. For Rip City.) 

Not only did Damian Lillard heed the Wynne call, other important Portland musicians joined:

  • Vursatyl – member of the Portland, Oregon based Hip Hop group Lifesavas
  • llmaculate (a.k.a. Illmac) – a St. Johns, Portland battle rapper and hip hop artist
  • KayelaJ – Portland-bred radio rapper and lyrical genius

Wynne made The Thesis in Pioneer Courthouse Square (named after a monthly local hip-hop showcase, featuring the rap stars above).

She and Lillard both share the same vision. To grow the Portland music scene. “Portland needs representatives, and there’s a space for that here because it’s an underdog city and I’m an underdog. I want to help establish more of an industry scene here,” she told Willamwette Weekly in 2019.

Wynne’s lyrics are nothing short of powerful. She takes on white privilege, civil uprising, systemic racism without apology (oddly enough, because she was raised in Lake Oswego, which she  dubbed, “the whitest suburb you can imagine.”). Her parents taught her about equal justice and hard work, so when she went to college, she took a slew of political science, social, ethnic and gender studies courses. That, with a background of growing up sharing one iTunes account with her brothers (who only listened to rap and hip hop), was how her own music began to evolve. Not only did she understand the need for an authentic voice in rap – but she understood that, as a white person, she could bring something important to the game.

“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.” Wynne

Listen and learn.

Wynne – The Thesis (Official Video) ft. Vursatyl, Illmac, KayelaJ & Dame D.O.L.L.A.

For the city. By the city.


Been ill aka Venus Fly Traps
Seven brains in one body so I dream in IMAX
Anyone, anywhere, any time, go!
Your ego is eco friendly, you don’t want smoke
Inscribed in graffiti on your CD gate fold
My capital punishment will have your lower case closed
Like a dying man’s will
Clocks got hands with no feet cause
Only Vurs can make time stand still
G.O.A.T. defeat the elite peers
I Benjamin Button bars dog, and leap years
Top of the Eiffel Tower catching lighting in bottles
To see me you’ll need MRI’s and night vision goggles
Or a closed caption to crack your spy glass
Phony, you’re full of it and your raps need a gastric bypass
God the novice, I’m marvelous even on my hiatus.

The dean of the school wants to meet with me
Cause I’m teaching my teachers things
And my old bullies want to sleep with me, honestly
I should run for mayor
Little brothers think they’re bigger than me
I’m going full Boogie Cousins baptizing ’em it ain’t fucking fair
(Free for all!) They tried to take the charge, they stick em up like the bank
(Keep the ball!) I already made all of my lemonade
When Piza falls, you’ll finally get it straight
And I can tell my therapist we can head in our separate ways
I put my lipgloss to the face
Singing baby better hide the license plates
Baby face could get away with murder, my bitches
Give em Stitches like 626, who’s this?

Snow bunny gone abominable, ominous flow, time for the snow
Ride for my bros, hide all your hoes,
I am the chosen, get your shit sorted
Goddess to most, stop with the toasts, I’m not with the smoke
Apostle the joke swanned into the rookie of the year, Hunny.

Coming for my rivals spot, stunting while they’re idols watch
Ask me why I’m the goat and thought I’d act like I’m not
I pulled out a long ass scroll, how much time you got?
Don’t act like a boss when you’re Michael Scott
I write so much my wrist is feeling like its shot
Look forward to getting writer’s block so I can stop
So high I’m dropping acid floating by your thought bubbles
Laughing, poke ’em while they pop, macro-dosing, micro dots-
I bring a knife to gun fight and jump right in
They aren’t shooters lets just say I ain’t cut like them
I black out and make em wonder where the sunlights been
(Hell raiser) hell’s ray’s the only light to touch my skin
Ain’t a rapper on this planet that can touch my pen
To this day, my styles Wilder and I punch like him
Shit you must be on drugs like Slim.

Call Wynne Shady’s daughter again, end up in the trunk like Kim
These n swag jacking, mass capping they battle rapping
Keep it authentic, still eating,
I live in New Season’s, get paper not plastic
I already know what you think bitch, I’m telepathic
And to answer your question yes I’m magic, yes, I’m Zaddy
Been loving pussy since pussy had me
Cause love is everlasting, (everlasting, yeah)
Remember they thought it was a phase? A bad habit?
Now y’all wake cause I’m putting pussy’s in caskets
Thought I was capping, now they’re the saddest
Damn near passed her like “have at it”
Now I’m strapped up without a gat, pumping plastic
You take her to Olive Garden, feed her pasta n salad
I take her to Jack’s and brown bag it, eat it in the wagon
Later, beat it in the wagon
This shit is easy it’s funny I thought she was out of my league
But I popped my head up and now she’s so beneath me
They say Black Live’s Matter,
Sho ’nuff, it’s a shame they don’t mean me
Christianity divided the black race,
Still I love my race like I’m Luigi.

Feel the energy
You can’t top dollar with top D.OL.L.A.,
They gon’ remember me for centuries
Praying on my downfall, I’m praying for my enemies
I don’t want no credit these is real n tendencies
They chant my name in every city that I visit
Travel in the finest but was the man in the civic
They love you when you rich and respect you when you the trillest
Mommy, daddies, aunties, and uncles it take a village
Kick my feet up on occasion, fill my glass with some drank
Oil in my system tryna gas up the tank
Only time I’m tickled when I laugh to the bank
I got the devil in my life but I could pass for a saint
I only run with family members, the rest is all associates
Try to crack the circle then we acting inappropriate
We all get 24, but i be on some Kobe shit
From the gutter on my mother so you know we here