Photo by Adam Leonard

Photo by Adam Leonard

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. 

When I am not developing visual artwork, I perform as a standup 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. In August 2016, I released my first album, Whimper and Bang.

I can be reached at

My instagram is Calculations.

My twitter is @winslowdumaine.