Artists of New Haven

Lee Massaro


Lee Massaro is a City-Wide Open Studios artist whose primary medium is oil paint. They like to paint portraits and put a lot of focus on color. You can find their website here. The following interview was conducted by Annissa Carter of ArtSpace as a part of our Artist of New Haven program. 

Tell me about the Billie Eilish painting you brought?

I like to do portraits and people are my favorite subject. The photo that I found of her had all this cool jewelry and spikes and things and it drew me in. If it were just her then I think it would’ve been boring but something about the silver and the spikes made me want to paint it. Also she was pretty big at the time and people would come up to me and say “Woah you should paint Billie Eilish!” and I said “Alright sounds good!” so here we are.

It sounds like even though you don’t have as much space as you’d like you’re still making it work with you

All the marketing I do is by myself and the studio I have is literally just a corner in my room but I’m just grateful to have a roof over my head. I like to use oil paints, it’s kinda what I transitioned into after sketching, charcoal, and acrylic painting. But if I had more space I’d do more welding and sculpting because I like to build. I’m working with my old art teacher who is having a documentary made of him and we structured 15 chairs to hang from the ceiling to make it look like a tree and I’d like to do more stuff like that.

As artists we have to work with what we have and there’ve definitely been moments during quarantine where I was struggling to create. I have to deal with very little space and no privacy. I’d like to be able to throw my paint at the wall and make a mess and maybe not have to worry if my cat will step in cadmium red and I have to give him a bath… again. But it’s fine, it’s all in the moment and it’s all temporary and that’s what keeps me going.

Tell me about where you went to school

I started at Montserrat College of Art but then my life took a turn and the turn lasted for a while. I did keep trying to get back to school but after moving back to Connecticut I started at Pair College of Arts in Hamden and that’s where I found a home. It’s a great school for anyone who has really bad anxiety because it’s small and the teachers help you see color in a whole different way. They helped me open my mind to a whole different outlook to the point where I get tripped out just looking at leaves. They’re trying to shift more into contemporary art but it’s more of a realism school, which is what I wanted because I wanted to learn how to fool the eye.

Do you think the pandemic has changed the way you’ve been creating?

In the beginning of Covid I lost my job so I made some side money doing wash portraits of people and only charging $30. I know that my art was probably worth more but at the time it was making people happy and they were buying it so I was able to make due that way.

But it’s more so changed the way I view art and my life and money. It’s made me realize how important it is to prioritize myself and my life over friendships and relationships and realizing that at the end, we’re buried by ourselves or burned by ourselves, whichever way you decide to go. Either way, it’s all on me to take care of me and I can’t hope that I’ll be supported by my friends and family all the time, which I kind of already knew but it’s still worth it to keep going and keep working.

Covid made things a lot more real and also made us all realize that you really can’t plan for everything. With all the things that I’ve gone through I had to learn to adapt and live in the moment because really that’s all we have.

So you have a teaching job, tell me more about that.

That’s been wild and crazy but it’s been amazing and I’m beyond grateful for it. It’s my first year teaching and I teach pre-k to 4th grade. It’s been crazy because I have to fit 6 periods of art supplies into a cart and have about 30 minutes to disperse things, teach, and contain a bunch of 3rd graders but I love them so much. I have a bunch of cards from them saying “I love you” and things like that. There was a moment when I had to quarantine because one of the students came in sick, and when I came back it brought tears to my eyes how much those kids missed me. That’s what’s been keeping me going but it’s been crazy.

Most of the time I feel like I’m losing my sanity. I have a hard time teaching then coming home to disengage then engage in myself and my own work. On top of all that I’ve kept my quarantine job on this farm upstate but I’ve grown so attached to the animals I couldn’t leave and I can’t just give up on them. It’s the same way with the kids too, sometimes I don’t know what I’m doing but I can’t give up because I feel needed.

There seems to be a level of empathy you have, not just in your art but your work as well.

If you couldn’t tell I’m a huge sap, just a walking sappy tree. I and everyone has a choice to either harden our hearts based on how others or the world has treated us or not. There’ve definitely been times in my life where I’ve been hardened and bitter and there’s still moments when that comes, but I still believe in treating others how they want to be treated. Even this morning one of the fathers was dropping his daughter off to class and I stood in the corner and he said hi. For some reason what keeps happening is people will just open up to me sort of out of nowhere, and he opened up to the point where he got emotional and was almost ready to cry. It caught me off guard but then I thought “wow, how long was he waiting for someone to talk to about that?”, he just needed someone to listen to and that’s what I try to be for everyone because I feel like that’s what I needed.

One thing I’ve heard a lot from other people is that they feel a sensation or like really connected to that person. With all my portraits I try to be open to whatever it is that I see in their eyes and what I feel when I look at their skin and everything. When I’m painting I try to be open to what’s in their minds, hearts, and spirits and put that into their work. Connecting to people really influences a lot, even if I don’t know who they are I still like to feel that connection on some level.