3D
2D
Content Creation
Design
Isabel Lauren Loewe
Oct 19, 2025
For years, Zac Crawford has been frequenting Washington Square Park with his table set up. The value proposition is simple: in 10 minutes or less, Zac will draw you, a loved one, or a pet. We spent the afternoon with Zac while he worked, surrounded by friends dropping in, tourists with cameras, dogs weaving through folding chairs, and a steady rotation of strangers asking if he had time for one more.
Zac doesn’t talk about art in romantic terms. He sees it as repetition, something you commit to and sharpen over time. He’s drawn portraits at Ivy League galas, private proposals, and luxury events abroad, but the park still feels like the center of his practice. It’s where he built his business from nothing, and where he returns whenever the weather holds and the crowds are good.
How long have you been doing portraits in Washington Square Park? How did you get into it?
Pretty much the day after I graduated. I always came to the park to hang out, but I noticed that no one was doing portraits here. I got a banner, three chairs, and I just started. On my first day, I made $100 and realized I could pay rent if I kept at it. Over time, I optimized, I added a table, a guestbook, a QR code, and business cards. Trial and error, mastering it slowly.
Walk me through what your year looks like.
Mainly, the summer and fall are when I can really do this. There are a lot of variables like weather, police presence, and whether it’s too hot or cold. It’s very conditional. But I try to be out here consistently when I can.
Do you think being a technical person helped with the business side of this?
Maybe. The park shaped me, talking to all kinds of people, pitching myself, and learning how to read and connect with strangers. That helped with business. I’m not naturally super outgoing, but this helped me become more social.
What’s your drawing process like now?
I draw straight with a pen now. It cuts the time way down. At first, I used a pencil, but drawing live in pen forced me to get quicker and more confident.
Have you ever made a mistake mid-drawing?
For sure. But the speed helps; it keeps things fresh and forgiving. And the energy of drawing fast pushes me to be more expressive.
Do you keep any of your drawings?
I keep a lot in my sketchbooks, especially subway sketches. I do give away a lot, but I make sure to hold onto some that feel special.
What’s your happiest memory in the park?
A warm, beautiful day with a line of people. That consistency, making people’s day, keeps me coming back. Also, making $400 in one day helps.
Do you consider yourself a street artist?
Yeah, for sure. I’ve been doing this so long it’s become my identity.
Have you had negative experiences with the police in the park?
There was a big crackdown. They fined me $150 for an umbrella. There’s a vague rule about not erecting “structures.” We had to have Zoom calls with the City Council. It got political fast.
Do you make most of your income from this, or do you do other work?
This is the main source, though it’s seasonal. I’ve done other gigs like events, illustrated for startups, and got paid in crypto once. I’ve freelanced a lot.
What kind of events have you done outside the park?
I’ve done portraiture at yacht parties, college events at Notre Dame, Harvard, and Yale, private proposals, store activations, and even went to Egypt for a gig without ever meeting the client beforehand. They just flew me out.
I landed at midnight, a guy held a sign that said “Mr. Zac,” and drove me three hours to Alexandria. Wild, but unforgettable.
Do you get a lot of commissions now?
Yes, some are corporate, while others are personal. I have to balance them and prioritize. It can get stressful, especially with follow-ups.
Any nightmare clients?
A 90-year-old woman with a film crew who disliked her drawing said it didn’t look like her. But she still paid.
Do you ever feel burnt out?
I say yes to a lot. My schedule gets crazy. I love working, and I’ll work seven days a week, but I’m learning to find more balance.
How do you deal with stress?
Working out helps. And sometimes, just doing nothing, resting, watching TV, zoning out. I don’t have a magic answer.
Do you have a preference between portrait commissions and startup work?
I like both, but the direct reaction from people when they see a portrait they love is fulfilling. Drawing someone and seeing them light up, that’s everything. This park has the full spectrum of humanity.
Have you done celebrity portraits?
Not really, but I’ve had people tell me afterward that I drew someone famous and didn’t even realize it. I treat everyone the same.
What are you looking forward to?
A potential January trip with a big foundation that educates kids through art and science. We’re pitching a sponsorship now. Fingers crossed.
Do you see yourself doing this forever?
Maybe not forever, but I’d love to keep evolving with more travel, different formats. I want to explore new ways to make art accessible and connect with people.
What’s something you’d tell your younger self starting?
Don’t overthink it. Just start. Put your work out there and see what happens.
