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“We all lived through it. But one of the fun or interesting realizations I came to in reporting the book was… Can we curse on your podcast?”

“Yeah. Anything goes.”

“… Is just how much shit happened in the world between 1999 and 2015.”

Chris Smith is the author of The New York Times bestseller, “The Daily Show (The Book): An Oral History as Told by Jon Stewart, the Correspondents, Staff and Guests.”

He interviewed 144 people, including the host Jon Stewart, Craig Kilborn, Steve Carell, Stephen Colbert, Samantha Bee and so many other people.

“You know, Jon Stewart’s a guy who had an upper-middle-ish class upbringing in New Jersey, went to William and Mary, came into comedy sideways. He wasn’t sure exactly what he was going to do after college.”

I needed to know how Jon Stewart did it. How he redefined Late Night. How he broke out and rose to the top of comedy. And how he used humor to disrupt it all mainstream media, mainstream politics, the news.

“He would wear the same thing in the office everyday: a pair of work boots, a pair of chinos, the same t-shirt, the same Mets hat. And well, they’d rag on him about being a slob. There was—and not to get cheaply psychological—something Jon was communicating… He was simplifying a lot of the extraneous stuff and getting to work.”

Here’s what I learned from Chris Smith about comedy, change and the combination that changed the world:

1) Ask the right questions

Jon showed up every day and asked, “What was in the news? What’s funny about it? What’s our point of view?”

Everyday, I ask, “Who can I help today?” It keeps me open to the day. It gives me a fresh perspective. That’s part of reinvention.

Always looking. Always starting over. Always asking, “What’s missing here?” And then filling that gap.

2)  Change the format

Jon did a “Bush vs. Bush” segment.

First you see a clip of Governor Bush talking about Iraq and saying, “We’re not here to nation-build.” Then you see Bush as president saying the complete opposite. “We’re going to nation-build in Iraq.”

Jon didn’t point out the hypocrisy. He could’ve. But that wouldn’t have been funny.

Instead, he played dumb. He pretended he didn’t know it was the same person contradicting himself.

That’s what made it funny.

He removed knowledge from the situation. And got the attention of millions. Eventually, making real change. They even had an effect on some big issues.

“They made an eight or nine-minute mock detective movie. They took one veteran and tried to trace his paperwork through the Veterans Administration. They kept running into ridiculous roadblocks, but it was also moving. It gave you a sense of how much this guy was going through to get medical care,” Chris said. “That ended up shaming the Veterans Administration and changing a lot of those rules and regulations.”

He also transformed media.

“Loosely,” Chris says.

But, in old media you couldn’t find the truth like you can today. It would take weeks of research. Now with the Internet you can search and find anything. And turn it around in 24 hours.

Chris talked to Anderson Cooper. He said the mainstream media world was always aware of “The Daily Show.” They didn’t want to get made fun…

“And, inevitably, you did.”

3) Ignore the traps

“You’ve got, in many cases, a lot of ambitious, competitive, eccentric people,” he said. “You put them in a room and give them a deadline and that can lead to a lot of clashes.” But Jon didn’t get stuck in the trappings of show business.

Which is easy to do in any career.

But if you use your idea of how things could be to fuel creation, you get a leg up.

You get “The Daily Show.”

4) Live in two worlds

“What about when you were writing the book? Did you ever wish you were them? Did you ever feel like, ‘I’m covering them, but I want to be them’?”

I knew my answer. And Chris’s answer was more or less the same.


“In some fantasy world… sure.”

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