Nick DiLollo
- Anna Lilli Garai
- Nov 11
- 4 min read
Nick DiLollo is a cartoonist and designer from Milwaukee and Chicago. He works across books, comics, album covers, and zines. Humor, discomfort, and surprise are key to his work. Growing up in an unconventional environment, he tells stories by questioning what feels familiar. Pieces like “The Nerve Endings” and “WOWIHATEPAINTINGBUT” mix honesty with absurdity, turning everyday moments slightly off-center. Alongside his independent projects, he collaborates with local initiatives and larger brands, keeping his unique voice at the heart of everything he does.
Q: You often turn everyday scenes into something absurd or unexpected. What usually sparks that shift for you?
A: The natural absurdities of everyday life spark that shift for me. I have never experienced the same day twice and really connect to the idea of expecting the unexpected. I have been known to rigidly plan and try to cling onto control of outcomes. In those experiences, almost every time, something unexpected happens. I find humor and comfort in that. For example, in my piece “The Nerve Endings” I explore the concept of a garage band getting interrupted by a car pulling in. I feel like in a lot of stories there is a clear-cut A–B narrative where the expected outcome happens. My work generally is shifting the expected perspective to one unfamiliar, offering a chance to explore what could be in relation to what is.
Q: Growing up outside a “traditional” setup shaped how you see the world. How does that background still show in your work today?
A: My non-traditional background shows up in terms of the subject matter of my work as well as my process. Being exposed to alternative lifestyles and family systems from such an early age allowed for me to question tradition and norms altogether. In having that fear of questioning and exploration taken away so young, I have been given an incredible privilege to create work that speaks to those concepts. This, in turn, allows for my work to be a safe place where people can explore ideas and feelings they may have never been able to. As it relates to my process, this has shaped the way that I work entirely. I have ADHD and find it incredibly difficult to sit down for long periods of time directing all of my attention to one project. Instead of forcing myself into a routine that I know will not work for me (this isn’t to say I haven’t tried to shove that square peg into a round hole), I allow myself to work in ways that are unconventional and in bursts since traditional methods don’t always work for me.
Essentially, growing up in a non-traditional environment has allowed me to explore and experiment without fear in a variety of ways.
Q: In “WOWIHATEPAINTINGBUT,” there’s a mix of playfulness and tension. Do those opposites come naturally to you, or do you build toward them?
A: I would say it is a mix of both. Amplifying the absurdity of everyday situations is a major theme throughout my work, so those concepts go hand in hand. In “WOWIHATEPAINTINGBUT,” I depict two grotesque figures locking tongues as an expression of their interconnectedness. In all of my experiences similar to that, there is a natural push and pull feeling in those moments of vulnerability. In my work I capture those natural opposites and visually amplify them. Through visually amplifying those natural opposites, I am consciously building towards moments where I’m inviting the viewer to be an active participant.
Q: In your paintings, the ordinary turns strange but keeps a certain warmth. How do you know when to stop pushing that transformation?
A: I know it’s cliché but through a lot of experimenting, trial, and error. I have found methods of pushing these transformations but still find myself creating pieces where I don’t push the piece far enough or end up going too far. As time has gone on and I continue to grow my practice, I notice that the balance begins to find itself.
Q: Your work moves between comics, design, and fine art. Do you ever feel pressure to define where you belong?
A: All the time. I think it’s easy to try to slip into a rigid, binary way of thinking, especially in a time where things are more divisive.
I often find myself sitting at the intersection of all three mediums and feel that my design is too abstract for that world or too comic book-esque for the fine art world, etc. Whenever I feel myself closing the lid of the metaphorical box on myself, I remember that the best work I do is when I play and experiment. An essential part of my work is found in discomfort and not only in the weird, playful stories I try to tell. I find that it’s only fair for me to actively seek out that discomfort to inform my work. What I mean by that is, whenever I feel that pressure or start hyper-focusing on where my art “fits best” (which can be quite often), I take some time to reflect and channel that energy into creating the work. This usually leads to the work finding where it fits best on its own or to the realization that I can create the space I belong in myself.
Q: You’ve collaborated with both brands and underground projects. What helps you keep your own voice consistent through all that variety?
A: Through the variety, I try to remind myself what I was asked to do and why. I try to keep in mind that the reason I have been fortunate to collaborate and participate in a lot of these projects is because of my unique voice. In reminding myself of that, I often am able to mute perfectionism just enough to get going on a project. Another thing that helps, especially when working within tighter parameters, is to detach from the outcome of a project. In releasing that control, I usually end up creating something that maintains my own artistic voice even within tighter creative constraints.