An interview with Jonathan MacGregor

button up
Oil on canvas


I think for any creative, world-building is a big undertaking that pushes the limits of creativity. Thinking expansively to create an environment, society, and characters that serve a purpose to explore that world is a continual showcase of imaginative prowess. When that process comes together it creates a rich, imaginative world one can easily get lost in.

This month’s Vagabond City artist is Jonathan Macgregor. A figurative-based artist raised in Georgia. Jonathan is a world-builder that explores the magic and dark truths of modern American regionalism.

wrinkle free
18 inches x 24 inches
Oil on cradled wood

Christian: How would you describe yourself as an artist?

Jonathan: I think it’s a fusion of the tradition of American realism fused with religious iconography fused with French romanticism.

Christian: What about your artistic style? How would you describe that?

Jonathan: Myself as an artist… I’ve always been obsessed with things. So if it’s a movie, I’ll fixate on it for like 15 years. I won’t accept other people’s opinions if they think it’s bad or anything. So when I bring my personality to themes or my work, I feel like that’s kind of my approach to art. 

Take for example if I’m obsessed with religion I’m gonna go full force. I’m gonna research all about it; find out as much as I can. Then I’ll take that research and infuse that into the work I do. It’s kind of like, I get addicted and obsessed with things, and that’s my approach.

trials of youth
12 x 12 inches
Oil on cradled wood

Christian: Do you have any inspirations for your work? And if so, does it change often?

Jonathan: It’s been changing a lot quicker nowadays. I’ve been recently consuming more film, and on TikTok I’ve found a little community to discuss that obsession with. 

Before I started looking at film and thinking about cinema, my portraits always felt like they were unaware that they were being painted, or if they were, they were kind of being voyeuristically viewed. But now I feel like all my paintings and portraits are now setting themselves up as characters to be viewed. 

Music is like having an even bigger influence in my work only in the sense of creating the environment, and creating the sound of like this sound for the piece, if that makes sense?

hang up before ‘hello’
6 inches x 6 inches
Oil on cradled wood

Christian: I gotcha. What are you listening to right now?

Jonathan: I’m really obsessed with Lily Kershaw. I love birdie. Matt Maltese. I’m like slipping into “autumnal melancholy.” But yeah, Matt Maltese honestly he’s been on repeat in my studio. 

Christian: Okay. I’ll have to give it a listen. So how has moving from Georgia to New York influenced your work?

stargirl, jenna
24 in x 36
Oil on canvas

Jonathan: I get inspired a lot by nostalgia and this concept of “picking and choosing” what you want to remember from your past. Because I think we all have the ability to remember and forget things that we don’t want; we kind of can cherry pick. 

So in retrospect, I’m appreciating a “mundane” aesthetic of the South. And this concept of your whole life being built and created for you by society. So like, you grow up, go to public school, go to a sorority/fraternity, then get married, have a kid, raise the kid, and repeat the cycle. Wash, repeat, all that stuff. 

lavender shadow
8 inches x 8 inches
Oil on cradled wood

So I’m appreciating that mentality. I don’t think it’s always the right mentality. It wasn’t for me. 

But I like that repetition. I feel like I’m infusing that into my work of this “repetition” of almost cliché image making, but there’s like a dark green darkness to it a little bit. Because I always want my work to have “synthetic” look that’s recognizable for people to catch. But then if you get the references and you want it to go darker, they’re obviously there.

Jonathan is currently based in New York City, NY and is an MFA candidate at the New York Academy of Art. His work can be found on Instagram @jongregor and his website