It’s a rare thing when a night out feels like a night in. But that’s exactly what the sold-out crowd that packed Massey Hall for comic Jon Stewart’s stand-up show experienced Friday night as they enjoyed a two-hour tête-à-tête with the sardonic and ever-popular host of The Daily Show.

Indeed, Stewart, casually clad in jeans and t-shirt, seemed completely at home in front of the giddy Toronto crowd, riffing about anything on his mind-which is to say, a lot. But it was when Stewart called for a beer halfway through the show (“What time is it? Eleven? Well, we should start drinking…”) that it became apparent that, for Stewart, this was less a performance and more of a night in with friends.

A veteran standup, Stewart knew exactly what buttons to press to fire up the Toronto crowd. “What do you guys wanna do now?” he asked during a pause. “Are there any hockey fights around here?” Taking the bait, the hometown fans began educating the comedian about the rivalry that is the Battle of Ontario.

“Hey, wait a minute-aren’t there any Senators fans here?” Stewart inquired, drawing a chorus of boos. “Hold on,” he interrupted, “We’ve talked about science, religion, the war in Iraq-and the only thing that provokes you is Toronto v. Ottawa? Can I tell you something? That’s what keeps you guys out of wars.”

Such well-honed stage instincts have translated well to the TV studio, where Stewart and his team of “news” correspondents have found a home aboard the flagship show of the Comedy Central network. After taking over the helm of The Daily Show from the almost funny Craig Kilborn in 1999, Stewart guided the show away from its sports tack and toward his interests-politics and world affairs-and, as a result, has seen the show’s ratings climb steadily.

To date, The Daily Show has garnered ten Emmy nominations and five wins, taking in 1.5 million viewers a night in the U.S., and nearly just as many here on CTV, which by Canadian standards are pretty impressive numbers.

But through it all, the comedian has remained unfazed by the hype. A multi-millionaire whose face is beamed nightly into houses all over the world, Stewart still comes across as the kind of guy who wouldn’t be out of place at a hole-in-the-wall bar in his native New Jersey, watching the game with friends.

So it’s an odd thing when one realizes that the man on stage-the one who, in between sips of his Heineken, just related the story of his dog’s bout with explosive diarrhea and told a tale of sex with piñatas-is the same person who has sparred with some of today’s most influential minds. But perhaps therein lies the secret to his success.

Stewart stands apart from the Jimmy Kimmels and Adam Corollas-both courtiers of the same demographics-of late-night television because of his ability to be highly inappropriate (and certainly irreverent) without ever being offensive. Indeed, Stewart mixes cheeky with enough charm to get away with almost anything.

When interviewing former senator John Edwards last week, for instance, Stewart asked if meeting former running mate John Kerry in the halls of Congress was for Edwards akin to the meeting of two kids “who had a gay experience at camp.” Edwards, with equal parts shock and amusement, took it all in stride.

Certainly, Stewart’s ability to discuss topics that wouldn’t be out of place on CNN while at the same time keeping the conversation unpretentious-and, frankly, hilarious-has spelled immense success for the funnyman. He comes across as one of us-a kid in a politician’s suit, someone who can mention Playstation and the Patriot Act in the same breath, a relevant and important voice for both the detached teen and the Capitol Hill veteran.

Which helps to explain the markedly mixed-bag audience that filled both his shows at Massey Hall (promoters added a second late set after the first show sold out). Fathers and sons, middle-aged couples, and as many youngsters as could afford tickets filled the rows, howling together and enjoying a night in with one of America’s top-and most unlikely-social voices.