Pensive Trust: The Portraits of Dmitry Samarov

rae_©_Dmitry_Samarov Rae Robinson | Gouache on paper | 15x18 inches | © Dmitry Samarov 2008

Portraits are tricky. There’s nothing more primal and fundamental a painter can do than reckon face to face with another living being. But portraits, unlike, say, landscapes or still-lifes, tend to only have meaning for the sitters or those who know them. I’ve sold very few to strangers. Most are either commissioned, bought by the sitters or family, or given back to them as gifts.


I’ve done three shows devoted solely to portraits. All three were at taverns. The first and second were at the Rainbo Club in 2001 and 2008, the third at Rogers Park Social in 2016. They were a good excuse to spend time with friends and now serve as mementos of times past.

Aaron Henkin | Oil on zinc | 6×8 inches | © Dmitry Samarov 2001

Aaron Henkin used to be in bands around Chicago. He lives in Baltimore now and hosts an amazing show called Out of the Blocks on public radio.

Mike Krezmien | Oil on board | 11×12 inches | © Dmitry Samarov 2001

Mike Krezmien fronted a band called the Country Melvins but is now a tenured professor at UMass Amherst. He works on education for troubled and incarcerated youths.

Rob Lowe | Oil on board | 11×12 inches | © Dmitry Samarov 2001

Rob Lowe worked at some of my favorite bars and video stores around town. He moved to the East Coast and still makes music and art, as far as I know.

Kelly Hogan | Gouache on paper | 15×18 inches | © Dmitry Samarov 2008

Kelly Hogan was and is an amazing singer. You can catch her on tour with Neko Case and The Decemberists, or better yet, at local bars like The Hideout.

Rae Robinson | Gouache on paper | 15×18 inches | © Dmitry Samarov 2008

When I met Rae Robinson, she was working at Cal’s Liquors in the Loop. Not only is that bar gone, but the building it was in was demolished and replaced by a steel and glass eyesore. She’s still slinging drinks—now at some fancy joint in the West Loop—and I’m happy we’re still friends.

Alexander Samarov | Graphite on paper | 9×12 inches | © Dmitry Samarov, early ’00s

Alexander Samarov is my father. He has posed for countless drawings and paintings going back nearly forty years. He’s always got a book going which makes him a willing subject.

Shay De Grandis | Gouache on paper | 11×14 inches | © Dmitry Samarov 2012

Shay De Grandis and I were a couple for five years but we’ve known each other for over twenty now. Judging by her expression in this portrait she wasn’t super thrilled with me.

Steve Badauskas | Gouache on paper | 18×22 inches | © Dmitry Samarov 2016

Steve Badauskas runs Bernice’s Tavern in Bridgeport. It’s located about a block from my place and I worked there for a time.

Rachel Lewandowski | Oil on zinc | 6×8 inches | © Dmitry Samarov 2001

More and more of my portraits become memorials to people who’ve passed. Rachel Lewandowski was very much alive when I painted her portrait. We had a complicated relationship which wound up hurting a bunch of people close to us. I’d had no contact with her for several years when I heard she had died.

Lee Sandlin | Sumi ink on paper | 11×14 inches | © Dmitry Samarov 2014

Lee Sandlin was an amazing character I wish I’d know longer. I made his portrait from photographs for his wife, Nina, after he died suddenly in 2014.

Eddie | Gouache on paper | 10×13 inches | © Dmitry Samarov 2016
Callie | Gouache on paper | 11×14 inches | © Dmitry Samarov 2017

In the past few years I’ve made a part of my living painting pet portraits. I wouldn’t have been caught dead doing a thing like this when I was younger but life has a way of humbling you and drawing dogs beats the hell out of driving a cab. In the end, I don’t see them as very different than the ones of people. If it’s got a face, it’s worthy of a portrait I figure. Eddie is one of Kelly Hogan’s dogs. Callie belongs to a woman who saw a bunch of my dog portraits at a kennel on Chicago Avenue. After I delivered it, she texted me that she was obsessed with it.

None of my portraits of people ever got a reaction like that. 


Dmitry Samarov was born in Moscow, USSR in 1970. He immigrated to the US with his family in 1978. He got in trouble in 1st grade for doodling on his Lenin Red Star pin and hasn’t stopped doodling since. After a false start at Parsons School of Design in New York, he graduated with a BFA in painting and printmaking from the School of the Art Institute of Chicago in 1993.

Upon graduation he promptly began driving a cab—first in Boston, then after a time, in Chicago— which eventually led to the publication of his illustrated work memoirs Hack: Stories from a Chicago Cab (University of Chicago Press, 2011) and Where To? A Hack Memoir (Curbside Splendor, 2014).

He has exhibited his work in all manner of bars, coffeeshops, libraries, and even the odd gallery (when he’s really hard up ).

He no longer drives a cab.

He writes dog portraits and paints book reviews in Chicago, Illinois.

You can see more of his work than you’d ever want to at his website.