Artist of the Week

Leroy Winter

November 22, 2023

Leroy Winter (b. 1998) is a painter currently working in Chicago, Illinois. In December of 2021, he graduated from the School of the Art Institute of Chicago with a Bachelor’s of Fine Art. His work has been shown at Martha’s Contemporary (Austin, TX), Sulk (Chicago, IL), Platform, the SAIC Galleries (Chicago, IL), and most recently, Innertown Pub (Chicago, IL).

Tell us a little bit about yourself and what you do.

My name is Leroy Winter, I primarily grew up between Texas and California. Right now I’m based out of Chicago, where I’ve lived since 2017. I’m a painter and a musician. I love people, and I think you can learn something from anybody.

Mirage, Acrylic and Graphite on Canvas, 24 x 30”

Could you describe your practice?

I’ve always been fascinated by how American history relies on mythmaking and narratives. In general, I believe that people use their own fabricated narratives to form an understanding of their past and the world around them. In many ways the world is volatile and confusing and people have always reduced the amorphous nature of their surroundings into something comprehensible and linear. I’m particularly interested in the way that early settlers in America have established narratives such as manifest destiny to rationalize their conquest, and how this rationalization formed the basis for a modern American identity in crisis. Having spent a considerable amount of my childhood in Texas, over time I obtained an interest in cowboys and other symbols reflecting the mythological “West”. As this iconography became a larger focus within my work, I was simultaneously becoming more interested in abstract painting, particularly that of color field painters. Gradually a parallel formed between the subject and materiality of my painting, where the transparencies of thin layers of paint reflect the hollow and faded ideologies that these symbols represent.

What/who is influencing your work right now?

As of now, the artists who are the most influential for me are Albert Oehlen, Silke Otto-Knapp, Jeremy Blake, Sue Williams, Jason Fox, and Morris Louis, among others. These are artists who I think about the most consistently, and they all either possess elements of humor or sublimity; in some cases they present both. These qualities, particularly when they’re paired together, are really important to me and I’m intent on reflecting that balance of humor and the sublime in my own work.

Describe your current studio or workspace. 

For the past year I’ve been working in a studio that’s in between North Lawndale and Little Village. It’s situated on a floor of a warehouse that a number of other artists also rent studios in, and recently I started splitting the studio with my friends Harrison and Biffy. The studio is pretty spacious so it allows me to share it with others and still have a lot of room to make larger works and essentially just make a huge mess. It’s a great space, everyone there is awesome and making good stuff so it’s cool to occasionally be nosy and leave my space to see what other folks are doing. It also has a nice roof that I like to watch the sunset from.

Untitled, Charcoal on Paper, 22” x 30”

What have you been reading and listening to lately?

Funnily enough, I just finished reading Mythologies by Roland Barthes and I would highly recommend it. Barthes is a pretty engaging writer and the way that he dissects mythological imagery and speech and shows you how prevalent it is in the media, politics, and consumer culture is really incredible and even ominous. His writing is still very relevant today and has played a big part in shaping how I look at art and the media. Right now however I’m reading a selection of short stories, Go Down, Moses by William Faulkner, who is probably my favorite fiction writer if I had to pick one.

As far as music goes, when I’m in the studio I primarily put on ambient music to space out. I love artists like Stars of the Lid, William Bassinski, Windy & Carl, Jim O’Rourke, Ryuichi Sakamoto, etc.

Wisp, Acrylic and Colored Pencil on Canvas, 24 x 30”

You often depict cattle, horses, and other large animals in your work. What is the significance of this motif? 

That series was a result of focusing more specifically on creatures that are commonly associated with the frontier, such as vultures or horses and cattle as you mentioned. I was interested in portraying these animals as hallucinations or wisps that appear on a desert horizon or in dense woods, serving both as a representation of a faded past and a depiction of nature being encroached upon by settlers.

Additionally, while making these paintings I was thinking about American pastoral landscape paintings of the 19th century, such as those made by Asher Durand. These paintings are compelling to me because of their inherent contradictions, as they depict the grandiose beauty of this country while also undeniably existing as a fabled portrayal of nature waiting to be conquested.

My recent work also stems from a fascination with the past but in reference to a different time frame and context. In Tinchel, my solo show currently installed at Innertown Pub, I presented a selection of charcoal drawings that reflects the direction my work is taking. The show title is a Scottish word that refers to a ring of hunters enclosing on game, alluding to the manner in which the figures are shrouded in thick trees. These drawings loosely reference photographs from the late 1950s, consisting of teenagers posing in front of various fast food chains in Conroe, Texas, where my great uncle grew up. Something about these photos were strangely captivating to me and felt like ominous and lingering relics of the past. As I worked on the drawings, I tried to make sense of these photographs which were mostly void of context and vaguely melancholic, while feeling an implacable connection to the subjects of the pictures and their varying expressions. The figures in these drawings maintain a similar phantasmagoric quality to my earlier paintings, but are more specific in regards to time and place, and perhaps more personal as well.

Untitled, Charcoal and Graphite on paper, 22 x 30”

What do you do when you’re not making art?

Recently I started playing drums in my friend’s band, National Photo Committee. It’s been really fun, everyone in the band is great and funny and I’m grateful to be a part of it. I believe we’ll be recording soon, but in the meantime they have a number of live recordings on bandcamp that y’all should check out.

Where do you see yourself, and your art, in five years?

Ultimately I want to teach, either with children or at the college level. To me teaching seems like a worthy pursuit, but the more I do my own research or talk to people who work within this profession I come closer to the conclusion that it is somewhat of a dismal path. Hopefully this isn’t the case and it is worth it, as I’m applying to grad schools for next Fall partially so that I can teach in the first place. Regardless, in the next five years I probably won’t be living in Chicago but will hopefully be surrounded by good company.

Western Apparition, Acrylic and Graphite on Canvas, 15 x 20”

What’s your favorite thing about Chicago?

The breaded steak sandwich at Ricobene’s.

What’s the last thing you saw that was truly inspiring? 

My friend Nell makes many fantastic cakes, but the most recent one was this absolutely insane birthday cake she made for my friend Gabriel. It was a Tres Leches inspired cake that was adorned with an evil screaming face that was made from blood red guava jam and pine nuts for teeth. The face looked as though it manifested itself from some cold and distant hell but it tasted so sweet. I’m usually not a fan of Tres Leches cakes but this cake was one of the most delicious cakes I have ever had the pleasure of eating.

Nell’s Cake 


Interview conducted and edited by Emma Kang James.