Photo by Chris Santiago

Photo by Chris Santiago

You can read more about my process in Voyage Chicago and The Daily Nonpareil.




I am a multidisciplinary artist living in Chicago. My lifelong fascination with pain, grief, and mental illness has served as inspiration throughout my life, helping me refine my intentions and sharpen my skills as an artist. My goal is to represent suffering as a complete picture: to present the experience of pain or heartache as overwhelming, oppressive, sickening, and alienating. In 2017, I completed the illustrations for The Tarot Restless, a complete overhaul of the classic tarot deck set in a morbid fantasy universe. I also wrote Restless Meditations, a book of interpretations and short stories that accompanies the deck. I’ve since sold out of the first edition of the deck, released a second edition, and I am presently working on a third and final iteration of Restless that will include the 12 cards of The Zodiac Retrograde and the 10 cards from The Inimical Oracle (The Exalted and Exterminated).

When I am not developing visual artwork, I perform as a stand-up comedian. My acclaimed work in comedy continues with many of the themes seen in my visual works, resulting in performances that are both furiously aggressive and deeply emotional. I’ve been chosen to appear on Crom Comedy festival, Beast Village, and I was selected by Kyle Kinane to open for him in Omaha and Chicago. In August 2016, I released a collection of my favorite performances called Whimper and Bang.

I can be reached at

My instagram is Calculations.

My twitter is @winslowdumaine.