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Barry Blitt, New Yorker political cartoonist and a Roxbury resident

Canadian-born Barry Blitt came to New York in the 1990s to pursue a career as an illustrator. While he had been working in Canada, he felt the move to the big city would further his exposure. And indeed it did. In addition to countless prizes and accolades, in 2020 he was awarded the Pulitzer Prize for political cartooning. The Roxbury resident has contributed more than 80 covers to The New Yorker, including the famous Obama fist bump cover, as well as many depicting Trump.

You started drawing at an early age but didn’t really consider it a calling.

Like all kids, I was plopped down in front of crayons and paper when I was quite young, essentially to keep me amused and out of the way. My grandfather used to copy Norman Rockwell pictures, so I had him as a cheerleader. I was drawing Popeye a lot; I was a big fan. A lot of the early work I did was sort of hero worship. I remember drawing a lot of hockey players and baseball players and Elton John and rock stars and stuff. 

What was the first piece you got published?

When I was a teenager, I was a rabid hockey fan — I still am — and I ended up doing illustrations for a couple of yearbooks: the Philadelphia Flyers’ and the Pittsburgh Penguins’. A friend typed up a letter and sent it out to a bunch of hockey teams and a couple of them responded and I did drawings for $25 a pop. I thought it was the greatest thing.

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When did the first big break come that made you feel you were really a professional?

I was getting work published in Toronto and made a couple of trips into New York. I took my portfolio to Chris Curry at The New Yorker. It all just sort of happened organically. I’m not a good businessman and I don’t promote myself particularly well. It’s best I don’t talk to anybody lest I alienate myself. I started doing some interior drawings and then Tina Brown, who was editor-in-chief at the time, wanted one of my sketches to be expanded into a cover. 

What was it like to have your illustration on the cover of such a prestigious magazine?

When I saw my first cover in print I was sort of like I often am: ‘Oh, why didn’t I do this?’ or ‘Why did I make that color?’ That’s pretty par for the course with me. Given the opportunity, I have a peculiar compulsion to redraw something over and over.

You have become known for your scathingly amusing portraits of the political scene. Do you generally follow politics?

I did not grow up in a political household and it wasn’t my thing at all. When I started sarcastic, smart-alecky stuff, I wound up with a regular cartoon in Entertainment Weekly. It seems when Monica Lewinsky entered the scene, political stuff became pop culture stuff. I drew Bill Clinton a lot, but wasn’t by choice — it just sort of happened. 

And then along came Trump. How did you approach the task of drawing him?

When I see a picture of someone or something I want to draw, I put it in a folder. Every picture of Trump is a revelation, at any angle. His facial expressions — he really is a cartoon. Needless to say, his hair is the most obvious feature to play on. The back of his head is fantastic and his eyebrows are amazing. His overbite and his series of chins and the color of him and the texture. He’s like an instruction manual of how to caricature someone. I mean it’s just all there.

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You’ve done so many Trump covers, is there one that is your favorite? 

The first cover I drew was of him diving into a pool — you always remember your first. My favorite one would be the one where he’s in a little kiddie car. The flat watercolor that I got on his jacket, I like the way the color adhered to the paper. It all worked.

So now here we are. What is life like after Trump?

Life after Trump is fresher, brighter, cleaner. It’s relatively boring, but in a good way. Political cartoons aren’t always a wholesome environment to start with, but there’s nowhere to go but low when a public figure is a dignity-free insult machine. There are less obvious targets to aim at, post-Trump, but less obvious is fine with me.

Any new obsessions?

Nothing as all encompassing and ubiquitous as Trump, obviously. Not yet, anyway. There’s a whole crop of hypocritical, un-self-aware congresspeople to draw. And things are volatile in the country and the world, so there’s no shortage of incentive to make cartoons. 

You won the Pulitzer Prize last year. Were you surprised?

It was completely out of the blue and unexpected. I got a call from the magazine’s editor on a Saturday night. It was strange in any circumstance. He said I won a Pulitzer and it was very surreal and exciting and nice. It was so amazing. I’ve tried not to get too obsessed about it. And now I am back to working and beating myself up every day. Resting on this kind of laurel is probably dangerous for me.

How have you been coping during the pandemic?

I hate to admit that I’ve been socially distancing for decades. The bulk of my time is spent at my drafting table or pacing around my studio, talking to myself out loud. When the UPS man comes to the door I hide to avoid conversation. This is nothing I’m proud of, but it’s old hat for me.

You live in Roxbury in a house that was once owned by Marilyn Monroe and Arthur Miller. Do you feel any vibes?

There’s a writing shed in the back where he wrote Death of a Salesman. I went up there with a drawing pad and thought I’d get some great ideas, and I got nothing. I am the least spiritual person. The pandemic has been great because it’s kept me inside and that’s where I’m most comfortable. 

This article appears in the June 2021 issue of Connecticut MagazineYou can subscribe to Connecticut Magazine here, or find the current issue on sale hereSign up for our newsletter to get our latest and greatest content delivered right to your inbox. Have a question or comment? Email editor@connecticutmag.com. And follow us on Facebook and Instagram @connecticutmagazine and Twitter @connecticutmag.