Two months into his new role as cohost of CBC Radio’s This Morning, I’m sitting with Michael Enright in Fran’s diner near Yonge and St. Clair. His trademark bow tie and suspenders have been replaced by a grey pullover, with a crisp blue and red plaid collar peeking over the top. As he speaks, he fidgets-with his collar, with his goatee, with his filterless cigarette.

Grudgingly, he has begun talking about himself. But when I’m halfway through my questions about the many jobs of his checkerboard career, he stops talking and leans dramatically toward me. “You have to understand something,” he says, his eyes narrowing. “On the scale of things, what I do now is very unimportant.” At first, I think he means that being a cohost on This Morning is insignificant, except then he says that what he did before was unimportant also.

“But don’t you have the power to change things?” I ask. “God, I hope not,” he replies, his trombone of a voice filling the room. He sits back and locks his eyes on mine. “Because I’m such a swell guy, I’d only change things for the better, right?”

While Enright talks he often stops mid-sentence to tell me how boring he is and how he would much rather ask questions about me (he does). I’m not sure if he’s being modest or just wants me to think he is, but I do know that he hates reading about himself and has never saved a copy of anything he’s written. He’s not without ego altogether, but self-aggrandizing doesn’t seem to be his thing. There’s also something distinctly bad-boyish about him in person-like an ageing James Dean-that doesn’t come across on the airwaves. He’s playing with a jackknife.

As he edges away from my personal questions, I find myself thinking of a poem called “Alone,” by Edgar Allan Poe (From childhood’s hour I have not been / As others were -I have not seen / As others saw-I could not bring / My passions from a common spring…). Only, I’m not yet sure why. Maybe the answer can be found in something said to me earlier by Enright’s friend, Ernest Hillen, author of The Way of a Boy. When I asked him why Enright is so respected for his writing and yet hasn’t written any books, he said, “You need to become fairly quiet inside to write a book, and I don’t think he’s a quiet man inside.” Hillen also said that with friends, Enright is often introspective but with other people he’s usually on, like an actor, with one-liners coming around the corner very fast.

If this is true, then Enright is treating me like a friend, because the man I’m having coffee with is more philosophical than funny. And when he does say something funny, there is never laughter in his eyes. His wit “is a very serious wit,” says Jack McLeod, a university professor and an old friend of Enright’s, “in the sense that humour usually comes from some deep culture or sadness.” And this is one of the most striking things about Enright. He seems to wear torment like a heavy coat of armour.

Three hours after sitting down to coffee, we are standing in a posh specialty store around the corner from Fran’s. Enright needs to buy a replacement martini shaker. He’s just taken one off the shelf and he’s explaining to me with self-taught erudition that a real martini should be served in a shot glass. A slender male clerk, who has been lurking in Enright’s shadow, steps forward and slips it out of his hand. “Let me get you one without fingerprints,” he says, heading for the back room. “I don’t need the box,” Enright calls out after him, then strolls over to the counter. The cashier, a polished blonde, demands his name and phone number. “Why, will I win a car?” he drawls, and avoids giving his name.

As he’s paying, he asks her why there’s a whole shelf dedicated to martinis. “Where are you from, another planet?” she asks. “Martinis are in.”

“That’s unfortunate,” Enright sighs. “I’ll have to find myself a new drink.”

If there’s one thing Enright can’t stand, it’s being like everyone else. While writing this piece I often wondered if his sole purpose in life is just to go against his notion of the status quo. Enright has spent his life questioning things and, through his career, questioning people. In the late 1950s he even questioned his own religion, dropping out of a monastery in Dunkirk, New York, after his first year. “He’s determined to see through the bullshit and you can relate that back to his abandonment of the Holy Mother,” says John Gault, a former journalist and fellow disaffected Catholic, who worked with Enright at Maclean’s back in the mid-’70s. “He’s a deep questioner in a society that doesn’t begin to question enough, in a media that’s become embarrassingly homogeneous.” Gault says that it is this suspicion and cynicism that enables Enright to question everyone-from celebrities to world leaders. And George Jamieson, a senior producer at As It Happens for the past 10 years, says Enright becomes cynical the minute “he smells the aroma of going along to get along.” Enright calls this brand of journalism approaching things on the bias.

“He loves controversy,” says Cate Cochran, who worked with him as a producer at As It Happens for more than five years. “He was impish in many ways about saying things that were deliberately provocative. Bratty is what he is.” But, more often than not, there’s value in Enright’s brattiness.

For example, in 1988, while Enright was the host of As It Happens, three whales became trapped in the ice off the coast of Alaska near a village called Barrow. It quickly became a media zoo with more than 150 journalists from at least 26 TV networks worldwide. But while everybody else was talking about saving the whales, Enright was thinking about eating them. So he did an interview with a native from the village-the man who first told the community about the whales-who said if he had known there was going to be such a fuss, he would have killed them and hauled them out for food.

“If it doesn’t have a little grit in it, it’s not for him,” says Jamieson. “This makes him endlessly entertaining to be around. It can also make him a horrendous pain in the ass if he gets on a tear about something.” At As It Happens, the tedious issue for Enright was the environment. He thought the topic was boring-producers had to fight hard to get their stories aired. Tensions exploded behind the scenes on occasion because producers believed that the show’s listeners were interested in hearing about environmental stories, even if Enright wasn’t.