How Jon Stewart went from frat boy joker to a giant of political humor

It's not easy to startle Jon Stewart, but it happened one evening shortly after he had finished taping his program in front of a New York audience.

"Are you serious with all these questions about talk shows?" said Stewart while tossing a baseball in the air and chain-smoking Camels in an office whose decor appeared to be inspired by Frat Boy magazine. "People don't usually ask me about these kind of things."

These days, anyone would ask Stewart how he became the most award-winning, influential political comedian of the past 15 years, especially as he heads into his final four episodes as one of the last remaining grown-ups on Comedy Central.

But this was 1995. The program was "The Jon Stewart Show," a syndicated series in which sharp, contemporary humor took a back seat to his Moron Walk — a bit in which he killed time by speed-walking across stage while swinging his arms like a spastic drum major.

The show lasted less than a year, but drew some die-hard fans, including David Letterman, who put aside his allergy to social graces by appearing on the finale.

I also thought the kid had something special, which is why I went out of my way to pay my respects to him in New York. At the time, I praised him for delivering locker-room humor with a I-know-better-than-this attitude.

But the future master of ceremonies for two Academy Awards? The director and writer of the hard-hitting drama "Rosewater"? The benevolent king who knighted Stephen Colbert, John Oliver and Larry Wilmore? The man who shamed CNN's "Crossfire" into cancellation? A two-time guest at the White House for private meetings with President Obama because senior staffers considered him the Walter Cronkite for the millennial generation?

Not even dear ol' Dave could have seen all that coming.

"My first thought when he got the job was, 'Is he really the guy?' " said veteran stand-up Mike Brody, who emcees open-mike nights at Rick Bronson's House of Comedy in the Mall of America in Bloomington. Brody had gotten used to "The Daily Show With Craig Kilborn," in which the Hastings native used his Ted Baxter persona to satirize mainstream media — and little else.

"I just didn't think Stewart was serious or intelligent enough to host that show," Broday said. "That just shows you how good my instincts are."

Stewart's most distinct departure from the Kilborn version, co-created by Minnesotan Lizz Winstead, was to stop parodying the news and start pulverizing it.

By 2000, just one season into his stint, Stewart was anchoring segments for "Indecision 2000," a scathing indictment of political convention coverage, peppered with Lewis Black's I'm-mad-as-hell-and-I'm not-going-to-take-it-anymore rants.

The Peabody award-winning shakedown was quickly followed by a return to the airwaves after the 9/11 tragedy with Stewart choking back tears in the most emotionally stirring commentary in all of late night TV.

"The view from my apartment was the World Trade Center. And now it's gone," he said. "And they attacked it, this symbol of American ingenuity and strength and labor and imagination and commerce, and it is gone.

"But you know what the view is now? The Statue of Liberty. The view from the south of Manhattan is now the Statue of Liberty. You can't beat that."

Like his recent joke-free monologue on the Charleston church shootings, Stewart chose truthfulness over "truthiness" — and it paid off.

"Viewers can sniff out authenticity and they love it," said Brave New Workshop veteran Lauren Anderson, one of the best political satirists on the local improv scene. "He has had the ability to say to audiences, 'Can we just talk about this for a minute? Can we agree that this is screwed up?' I don't think people necessarily trust news anchors anymore, but they trust Jon Stewart."

One of the greatest attributes of "The Daily Show" is its unwillingness to talk down to audiences.

Just last week, Stewart put the Donald Trump bashing on hold to go deep on the proposed Iran nuclear deal, a topic that's over the heads of even some Washington lawmakers. No matter. Viewers may not understand all the wonkish details, but they appreciate the fact they're not being treated like Moron Walkers.

"Stewart never dumbed it down," said Tane Danger, co-founder of the Theater of Public Policy, a Twin Cities troupe that uses improv comedy to tackle complex issues. "The biggest thing he proved is that you can be smart and funny at the same time. You can play to people's highest intelligence."

That approach failed to revolutionize the comedy scene.

Brody points out that most club comics are too gun-shy to enter the increasingly divisive arena of political humor. Plus, a routine riffing off the latest headlines is stale in a matter of weeks, a drawback for beginning stand-ups who may need months to hone 20 minutes of material.

Stewart also didn't appear to have much influence on the current late night princes — Jimmy Fallon, Jimmy Kimmel, James Corden — who are more interested in playing parlor games with Justin Bieber than skewering Sean Hannity.

Could upcoming "Late Show" host Colbert and Stewart's replacement, Trevor Noah, completely fill the void? Sure — and Nancy Pelosi and John Boehner could run off together and open a B&B in Vermont.

"He was more than just a comedian," Danger said. "There isn't a model for what he was."

So savor Stewart's final week. This moment of Zen may not come again.

neal.justin@startribune.com • 612-673-7431