Wear Many Hats Episode 87 — Dessie Jackson

Hey everyone it’s Rashad and this is Wear Many Hats presented by Dahsar where we talk about your main gig then we talk about your side hustle.

Dessie Jackson is an illustrator, painter, and mixed media artist.

She works primarily with charcoal, pencil, and oil paint.

Her work has been featured in Nylon, VICE, Complex, you name it.

Dessie has work with music labels such as Epic Records and Equal Vision Records.

Do you skate? If you do, you probably have seen her guest artist boards for Real Skateboards.

Do you like music? You probably seen her cover for Balance and Composure’s “Light We Made” record.

If you don’t like music and skateboarding, damn you must not be fun to be around with but if you like to go to art galleries she has had solo exhibitions in galleries such as Philly, NYC, Seattle and Atlanta.

Dessie has done stop motion illustration lyric videos for Halsey, a video as well for Jon Simmon’s project Creeks.

She has also got into making stained glass flowers. Is there anything she can’t do?

Here we have Dessie Jackson on Wear Many Hats, how’s it going?

I could just put out a whole intro and we wouldn’t have to do this pod at all.

Congrats on selling all your stained glass flowers. When did you start getting into that? Now your style is definitely switching up and changing all for the best.

Where are you based?

How I know you is thru the Philly gang. 10 years ago right? I just got back from LA seeing Dan Centrone and we were talking about you. So that’s what made me think of you.

From Philly you moved to NYC then to LA.

I just went back to Philly, it’s different now.

I was watching your Adidas commercial and hearing your voice I forgot your related to Miley.

Do you still write for Vice? I did read your article entitled: I Shelter in Place With the Chaos of ‘The Real Housewives of New Jersey’ hilarious.

Or when you went to Coachella and your deposable film camera photos looked like Coachella was a lot of fun.


Has people approached you with having your art as NFT’s yet?


You just put out a collection with Samii Ryan. Lots of fun, cozy fits. The set design for the collections you put out with her are a full production. Flowers, a giant rainbow. The sweatpants look mad comfy.

You don’t ever have to buy clothes again, you could just wear it all day in the studio.

Do you do a lot of clothing collaborations?


I remember you did that live painting for Alina Baraz. How were you feeling when you did that?

I would be scared shitless.

If you could do a live painting for your favorite musician who would it be?

Your on paper illustrations are so detailed they look like psychological trillers like an A24 film. I feel like someone should make a stop motion horror film of them.

I just printed a bunch of the coloring pages to give to my friends kid which I know they’ll love.

Social Media

What’s your take on social media, people viewing your art, the likes, instant gratification?

Everything you said in previous interviews about seeing artwork in person is so true. When I go to art galleries I do see the rigidness of the canvases are stretched and not stretched.

Hats off

Hats off to you on all these things that you do, for some Wear Many Hats Dahsar solutions do you think bands ever had a line in their songs for sponsored content like hip-hop does? And would you ever do it?


If you were to get a chest tattoo quote what would it be?

Plug your socials where can people find you?

Thank you Anna for coming on Wear Many Hats, it was great to have you.

Till next time this is Wear Many Hats presented by Dahsar and I’m Rashad Peace!




Where we talk about your main gig but mostly your side hustle. Beyond the brim. Hosted by Rashad Rastam and presented by Dahsar.

Love podcasts or audiobooks? Learn on the go with our new app.

Recommended from Medium

Edward Hopper, Nighthawks, 1924

Explore, Collect and Build Art

Fresh NFT Projects From SEA

Random Rules — Why you should check out generative art

Weeping Madonna, Seething Dragon


Meet the Artist: Jérôme Comentale

Coastal Wall Art Pour Painting

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Wear Many Hats

Wear Many Hats

Where we talk about your main gig but mostly your side hustle. Beyond the brim. Hosted by Rashad Rastam and presented by Dahsar.

More from Medium

Garrison’s “Locals” Playlist

The Wizard of Oz: Dorothy, Toto and the People of Michigan


Harmony’s Story: A “Missing-Person Vignette”