Daily Inspiration: Meet Winslow Dumaine

Today we’d like to introduce you to Winslow Dumaine.

Hi Winslow, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I do a variety of things, so it can be hard to pin down exactly how it started.

I got on stage for the first time around 2013. I went to mics and shows in bars and taverns across town. Barley Street Tavern, now closed, was my weekly hang. I started drawing in a more collected and serious capacity around that time too. I’m not a drinker, so I would sit in the bars and draw in the low light.

I think the slapdash approach to my early work was guided by the dismal setting. It was like finding shapes in clouds – I would draw lightly in pencil when I could hardly see the paper and then ink it, every mistake and miscalculation, in full light. The result is more dreamlike and free than if I did the whole thing in the strict and unforgiving light of day.

After doing open mics for a few months, I won a comedy battle and that got me a little more attention. I got on a few shows, started one of my own, did some festivals, and after about four years, I moved to Chicago to pursue it more seriously. By that point, I had illustrated half of my deck of tarot cards, something that would become a foundational work and would spur more serious ventures into art and comedy for the rest of my life.

Now I’m going on tour with MC Leitsy, and we will be visiting Nashville, Knoxville, Huntsville, and many other cities in the great American South. Anyone who follows my Instagram can see dates as they develop.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way? Looking back would you say it’s been easy or smooth in retrospect?
In art, smooth roads are rarely worth taking. Navigating the lives and egos of others is part of the journey, and I don’t know that they can be described as part of the struggle. The only obstacle I’ve had has been myself.

The whole of my early career was, as I recall it, a stumbling near-wreck thanks to my emotional immaturity, arrogance, and self-destructive tendencies. Emotional immaturity and self-destruction are rarely rewarded, but I believe that it is only thanks to my arrogance – and whatever furtive talents I possessed – that I pushed on.

I have since attempted to trade arrogance for skills. Over the years, I have had to get over myself and learn how to be kind to everyone I meet. As for self-destructive tendencies, I cannot say I’ve made such broad strides. At the very least, I have moved on from explicit self-destruction, through harm and endangerment, to a mode more amenable to progress as an artist: I overwork myself to an exhausting degree.

Yet cracks appear even in that approach – there was a long time when I believed that I am nothing without my work. Now that I’ve released my tarot deck and I’ve toured the country for comedy, I feel as though I can take a brief – brief, mind you – a moment of rest. And then, it’s back to work.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I try to adapt and evolve my work to play off existing phenomena, allowing me to retain a unique voice as I grow. There are a lot of angry white men in comedy, and I say this not as a point of judgment.

A lot of my best friends are angry white men, and it is my default desire to perform with my hackles up, loud and frustrated with the world. I strive to make my comedy about heart and hurt, filtering anger through a place of yearning to convey a more sympathetic depiction of the emotion.

Instead of an excoriating rant, I create desperate, unhinged, surreal pleas for an off-kilter sensibility. For years, I was known as a dark, morbid, suicidal comedian, and I was writing from the heart. With the success of my visual art, I’ve relaxed and gotten sillier. It’s easier for me on stage. I’m more forgiving with myself and I’ve only gotten funnier.

As an illustrator, I focus on pen and ink, and as a writer, I stick to short stories and lore building. I’m likely known most for my tarot deck, The Tarot Restless, a massive and meticulously detailed deck of 100 tarot cards and a book with a short story for each card. Now, I’m working on a card game that is going to have around 500 cards, each with lore and functionality. I’m a maximalist.

I don’t think too much about what sets me apart from others because, often to my detriment, I tend to focus on my own work. I have trouble engaging with the works of other artists because I am so anxious to make my own. I have no interest in being the best in my field, as that is entirely up to the whims of others.

I merely want to be the best I can be, something that I can judge myself.

Do you have recommendations for books, apps, blogs, etc?
I don’t use many apps for my work. I record my sets and I engage with the usual social media diet, Instagram, Twitter, and recently Tiktok.

The only things that inspire me are works that are truly fully imagined and conveyed with an appropriate sense of scale and awe. If I am engaging in a fictional world, I find no interest in mundanity or near-real fantasy. I want it to be huge and terrifying.

As such, I am a sucker for atmosphere. I enjoy things that engulf the spectator, like the richly conceived worlds of Cormac McCarthy and Lovecraft, or the dripping nightmares of Dark Souls, Elden Ring, or S.T.A.L.K.E.R. video games.

My musical intake is similarly intense, consisting of grand scale cosmic horror from black metal bands like Akhlys, Wode, Suffering Hour, LVTHN, Nightbringer, and so on. Lingua Ignota, a one-woman extreme noise project from Kristin Hayter, has been a long-time inspiration.

Pricing:

• The Tarot Restless – $60
• Bumper Stickers – $2-5
• Enamel Pins – $8

Contact Info:

• Email: [email protected]
• Website: www.winslowdumaine.com
• Instagram: Instagram.com/calculations
• Facebook: https://www.facebook.com/WinslowDumaineArtist
• Twitter: twitter.com/winslowdumaine

Image Credits
Chris Santiago