Back in May, Klassen was sitting in a noisy café across from Toronto’s Trinity Bellwoods Park, near his brother’s house. He was in town for the Toronto Comic Arts Festival and the Harbourfront Centre’s children’s book event Festival of Trees, where This Is Not My Hat was up for the reader-nominated Blue Spruce Award. Klassen “actively miss[es] Canada all the time” and would desperately love to move back from Los Angeles, where he’s lived for almost a decade since graduating in 2005 from the animation program at Sheridan College. His California-born wife, Moranne Keeler, is not convinced, having experienced the polar vortex during their trip to Ontario last Christmas.

Klassen was already in L.A. – creating set design and concept animation for films such as Coraline and Kung Fu Panda 2 – when fellow expat Lucy Ruth Cummins, an art director at Simon & Schuster in New York, watched one of his animations on the now defunct arts blog Drawn. She contacted Klassen about turning the short film into a picture book. The project didn’t work out, but Cummins kept one of Klassen’s illustrations tacked to her wall for years.

“I knew Jon had the talent; I just needed to patiently wait for the text that would make sense with his work,” says Cummins. That text arrived in the form of Stutson’s Cats’ Night Out, and Klassen – recognizing that animation wasn’t where he belonged – found a new career.

“I’ve come to refer to folks like Jon as ‘geniusy type people,’” says Cummins. “These are people whose work seems completely organic and natural, who bring to the table not just one great idea but several, and who possess massive talent, but who are humble enough to be great collaborators, open to feedback, willing to revise. Jon is all of those things.”

After several more book-illustration gigs, Klassen decided it was time to try his hand at writing. The result was I Want My Hat Back. “I had a certain way I wanted the characters to look and behave – almost like they were bored with the story,” says Klassen. “I don’t think that approach would’ve worked, or even have occurred to me, if I had been dealing with somebody else’s text.”

I Want My Hat Back racked up the accolades, including a Theodore Seuss Geisel honour and a spot on the New York Times Book Review’s list of top illustrated children’s books of 2011. But the story – featuring a bear asking a series of animals if they’ve seen his hat, and eventually eating the rabbit (off-page) who has stolen it – caused some to clutch their pearls and question the rather unhappy ending (for the rabbit, at least; the bear is pretty chuffed to have his pointy red hat returned).

The same concern echoed for This Is Not My Hat, which follows a similar plot but is told from the point of view of the thief (a small fish who meets the same fate as the rabbit after swimming away with a bigger fish’s jaunty blue bowler). When the book nabbed the Greenaway, the jury praised its dark humour, but much of the subsequent media attention was paid to the story’s deadly conclusion.

Klassen has become fairly immune to the criticism, but still feels the need to defend his stories. “I hate cynical kids’ books and it bothers me when my books get lumped in with books that were done sarcastically or cynically,” he says. “That’s one of the worst things you can do in a kids’ book because then you’re not talking to them anymore, you’re talking over their heads.”

Sam and Dave Dig a Hole shares the same ethos as Klassen’s solo work: the humour is deadpan and witty, the visuals tell as much of the story as the text (and sometimes more), and readers get the sense we’re being cheekily winked at – like we’re all in on the joke. The book, about a pair of boys who set out to dig a hole in the field next to their house and not stop until they “find something spectacular” (they don’t, but something pretty interesting happens anyway), is also a rarity in modern kidlit: a true collaborative effort between illustrator and author.

Malk introduced Klassen to Barnett shortly after the former signed on with him almost six years ago. The illustrator and author became fast friends, bonding over ideas of what makes a great picture book and shared influences (Klassen counts P.D. Eastman and Arnold Lobel among his). The idea for Sam and Dave was hatched over breakfast in an L.A. coffee shop, the initial concept sketched out on a napkin. While working on the book, the pair kept an audio connection open between their computers for hours at a time, talking about the story and the images Klassen was creating (switching to pencil crayon from the Chinese ink he favoured for the Hat books).

“He would draw something beautiful or funny and I would have to go back and justify its place in the book with new text,” says Barnett. “But it didn’t feel at all like I was put upon to do that; it was like, ‘What do we need to do to get that art in?’”

The twist at the end, in which Sam and Dave wind up in what appears to be some sort of parallel universe, is presented visually: the weathervane bears a different animal, the tree dangles pears instead of apples, the cat’s collar is blue instead of red. Klassen isn’t sure how to define what happens, but he imagines that kids will figure it out and form their own theories, ideally without hints from adults.

“I think if you’re on your own as a kid and you figure it out, you get to own it,” says Klassen, who talks about sitting alone as a child and poring through old picture books from the 1950s and ’60s on visits to his grandparents’ house in Ontario’s Niagara Region (he grew up in Markham, Ontario, before moving to Niagara Falls when he was 12). “I think that’s my ideal experience of the book. [Kids] might even tell their parents about it and maybe read it later, grinning the whole time.”