they seem cool

The Painter Who Loves to Hate the Art World

Meet Dean Dempsey.

Photo: Shaniqwa Jarvis

Dean Dempsey does it all — he’s a visual artist, a writer, a director, and an actor. Yet he describes his work as “the only thing I can do” despite it spanning multiple mediums. “If I could be an engineer or doctor, I’d probably do that,” he said. “The art world is miserable, but I enjoy it.” He’s been an artist since he was a kid, when his grandmother would have him “paint what you feel” when he was upset. Now he shows his abstract paintings throughout Europe and New York. We spoke with him about absurd holidays, Goodwill, and Yoko Ono.

What is your most-used emoji?
I always use the weeping one. It’s overly dramatic about simple things. I also use the upside down smiley face when I’m happy. Because it’s too good to be true.

What is your favorite holiday?
Christmas because it’s absurd. The myth about Santa and flying reindeer and a fat man going down the chimneys is just absurd and it’s colorful so it’s great. Forget the presents — the paper is the best. Groundhog’s day is also pretty good. It’s a rodent that predicts the future.

If you could spend three months anywhere, where would it be?
Istanbul.

What superpower would you have and why?
To tell the future because I think we all want to win the lottery.

What’s the best album ever made? 
It changes by the week. Right now, I think Yoko Ono’s Yes, I’m a Witch Too.

Who do you think is cool?
Strangers who aren’t concerned about how they appear to other people, but who are still glamorous and beautiful. Authentic people.

Go-to karaoke song?
“Passenger” by Iggy Pop.

What fictional character would you want to hang out with?
Henry Chinaski by Charles Bukowski, but only in 1970s Los Angeles.

If you could speak to animals, which animals would you want to talk to?
My cat, only my cat, because I could find out what she’s staring at when she’s staring blankly at the walls.

Jeans or sweats?
Underwear.

What’s something your social-media followers don’t know about you?
Eh.

What was the last website you looked at?
The DMV website. I need to get a driver’s license.

If you could be outfitted by one designer for the rest of your life, who would it be?
Goodwill couture.

What do you eat for breakfast?
Whatever I didn’t finish for dinner.

If you could only eat three things for the rest of your life, what would they be?
Beans, bananas, and matzo balls. I’m like an old man, I just want mushy food.

If you were a color, what would it be?
Clear.

Photo: Shaniqwa Jarvis

Dean wears a Dior Homme suit.