Lisa Rogak - Angry Optimist

LET’S GET SOMETHING out of the way from the beginning:

Jon Stewart is a bundle of walking contradictions. On the one hand, he makes no bones about exactly how he feels about things at any given moment, delivering his opinions and thoughts to his audience seriously—usually with an eye toward making them laugh—while also hopefully making them question the way the world works.

On the other hand, he is a man who hides in plain sight. Stewart is an enigma who shuns the spotlight, and his contempt for certain people and philosophies sometimes makes him so enraged on the show that he starts to shake and spit.

“[I’m] a bitter little hairy man of comedy,” he has joked.

Actor Denis Leary predicted his friend’s progression way back in 1994 during Stewart’s first talk show: “Jon’s shown more of his nice-guy side so far,” he said. “As the show continues, it will get uglier. Eventually it will just be this raging little Jewish man screaming into the camera.”

Some days, indeed, that man seems not so far away.

At the same time, the man is comprised of a peculiar mix of anger and optimism, in almost equal proportions.

But the inescapable truth is that Stewart is so damn funny that even the targets of his often caustic observations appreciate his jokes and even laugh at their own foibles as expressed through his eyes.

By his own account, Stewart says he was born with an unorthodox sense of humor that needed to be let out. “I can’t remember not being this way,” he said. “I can’t remember one day thinking, ‘You know what might work for me? Humor.’ My brother was smart, so there was no way I was going to cop that title in the family, so I naturally gravitated toward another direction of attention: I was the court jester of the family.”

At the same time, his humor leans toward taking the side of the underdog.

“He has this internal barometer of what’s right and wrong,” said Madeleine Smithberg, former Daily Show producer. “He has a very sensitive justice meter. He’s just way too smart for that little body.”

“My comedy is about anything that, when I was growing up, made me feel different or disenfranchised in any way,” he explained.

As a result, he developed the tendency to constantly look over his shoulder. “I’m nervous about everything,” he admitted.

“Jon is driven by the forces of guilt and shame and fear of being on the outside that give Jews their comic angst,” said Ben Karlin, who worked with Stewart on The Daily Show for many years.

“Jon is a neurotic nut,” added comedy writer Adam Resnick.

Stewart agreed, up to a point. “My comedy is not the comedy of the neurotic,” he said. “It comes from feeling displaced from society… because we’re not in charge.

“But I am probably a lot more critical of things than I should be.”

For someone who is so widely adored and respected, Stewart insists that his rise to stardom was unplanned. “People who worry about where they’re going next generally don’t end up where they think they’re going,” he said. “When you’ve got too much of a master plan, it’s going to fail.

“As a kid, I never thought, ‘I want to be a talk-show host,’” he said. “Some people growing up gazed into the sky and every cloud looked like Johnny Carson. I just wanted to be a good comic. And that was only after I got out of school: ‘Well, what do I do now? I like to sleep late and I don’t like working.’”

Critics, pundits, and fans all try to parse the man, sometimes from surprising corners—Republican congressman Paul Ryan has called Stewart the funniest man in America while New York Times columnist Paul Krugman accused Stewart of “ruining his brand” by dismissing the idea of a trillion-dollar coin—but really, he claims that what makes him tick is pretty simple:

“I think of myself as a comedian who has the pleasure of writing jokes about things that I actually care about, and that’s really it,” he stressed. “I have great respect for people who are in the front lines and the trenches of trying to enact social change, but I am far lazier than that.

“I am a tiny, neurotic man, standing in the back of the room throwing tomatoes at the chalkboard. When we come to work in the morning we say, ‘Did you see that thing last night?’ And then we spend the next eight or nine hours trying to take that thing and turn it into something funny.”

Regular fans of the show know that in Stewart’s eyes, nothing— nothing —is sacred. His rapid-fire wit often paints him into corners with people who have every reason to be offended, but luckily they’re laughing their asses off instead of being outraged. Stewart was a frequent guest on the Larry King show and he liked to poke fun at the host while pointing out societal hypocrisy and expounding on the current topics of the day.

“We think about all the wrong things rather than solve the problems,” he told the oft-married King back in 2004. “And we freak out by gay marriage. I mean, honestly, have you ever been in a gay marriage? I hope I’m not prying.”

King’s response: “No, I have not.”

Stewart: “I just thought, law of averages and all that. I mean, how many out of twenty, how many has it been?”

King: “Stop!”

Stewart: “Ten percent of the country is gay, and you’ve been married twenty times, so I figured two of them had to be—no?”

Stewart couldn’t stop being funny if he tried. After all, his humor has always been fueled by his deep sense of frustration at the injustice, lies, and hypocrisy that are everywhere he looks. “I’m attempting to scratch an itch, and I want to make humor about things I care about,” he said. “People always ask, where do the jokes come from? Really, they come from a place of pulling your hair out seeing things that make you cringe and wanting to turn that into something that will make you laugh.”

At the same time, he has no tolerance for self-analysis or a woe-is-me attitude, which is perfectly understandable since being constantly attuned to something you could feasibly turn into a quick laugh—and ego boost—can’t help but turn your view outward, at least when you’re in front of an audience.

So when Oprah put him on her couch in 2005 and promptly proceeded to start delving into the cause-and-effect of his life, he quickly waved away her probing questions.

“If you looked at anybody’s life, you could find the pain in it and say that what they do is born of that pain,” he patiently explained.

But Oprah wasn’t done. When she asked if he was teased as a child, he’d had enough, and shot back, “ Who wasn’t? ”

But he does admit that his childhood has unalterably shaped his life and sense of humor. “A part of me is probably still trapped in whatever emotional state I was in at fourteen years old, when my nose and head were the same size they are now, but my body was half its weight,” he said. “I think there’s a part of you that’s always stuck in that. And when you look in the mirror, and you evaluate what you’re doing, it’s always fractionally coming from that perspective.”