Canadian cartoonist Barry Blitt just won a Pulitzer. So why does he find Donald Trump so tough to draw?

Barry Blitt may not be a household name, but there's a good chance you've seen his work.

For nearly three decades, the Montreal-born artist has created evocative editorial cartoons for The New Yorker — and last week, he won a Pulitzer Prize.

The Pulitzer judges honoured Blitt "for work that skewers the personalities and policies emanating from the Trump White House with deceptively sweet watercolor style and seemingly gentle caricatures."

"It's very surreal, I have to say," says Blitt on the phone from New York in an interview with q host Tom Power. 

"It'll probably take months or years to sink in. It's not anything I expected. And it's weird."

Drawing Donald Trump

But even though Blitt has created countless cartoons and more than 100 New Yorker covers, it turns out he finds current U.S. President Donald Trump among the toughest characters to draw.

"He is a caricature already, and it's hard to satire a satire. What you put down on the page becomes redundant," says Blitt.

"He is a cartoon character to look at, and I find myself trying to normalize him sometimes. I remove one chin, let's say. And the hair has already been designed by an underground cartoonist. So it's frustrating."

When Blitt is online and sees compelling images of people he might caricature, he drags them onto his computer — and his file of Trump images is especially well-populated.

"The file on Trump is just jam packed because it seems like every photograph of him is a revelation. I've got files for side of head, back of head. It's amazing," says Blitt.

"From the back, even, there's no one else who looks like that. It's like frozen yogurt that's sort of cascading over a waterfall," he says with a laugh. "There are better metaphors. But he's an amazing specimen."

Much easier to draw are U.S. Vice-President Mike Pence ("He's got those deep-set eyes and he looks suspicious of absolutely everything," quips Blitt) and Steve Bannon ("beautifully unkempt"), as well as Trump lawyer Rudy Giuliani.

"The crew that Trump surrounds himself with, they're amazing cartoon faces. And Giuliani has become just more of a ghoul as he gets older," says Blitt, who kicked off his career in Toronto drawing for magazines including Toronto Life, Entertainment Weekly and Rolling Stone.

"You could spend a long weekend drawing his mouth, with those gums and the teeth and everything. He's great to draw."

'I always loved the way he drew'

Growing up, Blitt idolized the work of legendary Montreal Gazette cartoonist Terry Mosher, who drew under the name Aislin, and even met him at a book signing when he was around nine years old.

"I always loved the way he drew," says Blitt. "I probably didn't understand a lot of the cartoons. I was not and still am not particularly politically minded. I just loved the way he drew Trudeau and Mulroney and René Lévesque. I remember those drawings vividly. I still would love to be able to draw like that."

Blitt says when he draws he doesn't aim for deep political analysis, but rather for "absurdity, ridiculousness and a cheap laugh" as he carefully dances on the line between what's acceptable and what isn't.

'There are certain places you can't go'

And invariably, every once in a while he lands on the wrong side of that line.

In 2008, Blitt found himself the subject of headline news when his satirical depiction of Barack and Michelle Obama through a racist lens — in militant and Middle Eastern garb with an American flag burning in the fireplace and an image of Osama bin Laden on the wall — was mistaken for direct comment.

The outcry was immediate, and the Obama campaign called the cartoon "tasteless and offensive."

"There are certain places you can't go — and of course, that makes you want to try and go there," says Blitt.

"And I think that's maybe what the Obama cover was. I was looking for where the line was. I was across it — And sometimes you're just inside of it. And that's where the joke lies, I think."

Of course, editorial cartoons are designed to make people laugh. But is there a part of Blitt that wishes he could change people's minds?

"There's probably a small part of me that does. But then there's just a slightly larger part of me that realizes that's not going to happen," says Blitt.

"And so that slightly larger part of me tells the smaller part of me not to bother. So I don't worry about that."

Written by Jennifer Van Evra. Interview produced by Chris Trowbridge.