Lisa Rogak - Angry Optimist

“He’d been there a long time,” added Karlin. “He was never going to be the host, it was Jon’s show. But we didn’t want to lose him, so we tried to figure out what else someone like Stephen could do.”

They remembered those fake promos for the fake Colbert Report that had aired several times on The Daily Show . One day in the fall of 2003, when working on scripts for The Daily Show , the producers and writers had discovered that one segment was running a bit short.

Why not run a fake ad for a fake show starring a fake news correspondent?

They ran it by Colbert, and it sounded good to him. The writers came up with a promo for the imaginary Colbert Report despite the fact that the show didn’t exist.

“I tried to ape whoever was the loudest and rightest in prime-time cable news,” he said. They produced four of these promos, which ran through 2003 and 2004, and thought nothing more of it.

Executives at Comedy Central were looking to extend The Daily Show franchise, as were Stewart and Karlin for Busboy Productions. Perhaps the fake promos had planted the seed, but building a show around Colbert’s character seemed doable.

The O’Reilly Factor with Stephen Colbert was how they pitched it.

Once they started to flesh out the show, Colbert said, “But I can’t be an asshole.”

“You’re not an asshole,” said Stewart. “You’re an idiot. There’s a difference.”

Colbert agreed. “The audience wouldn’t forgive Jon for saying things most comedians would want to say,” he said. “But we can say almost anything, because it’s coming out of the mouth of this character.”

“The challenge of these things is how to evolve and keep it fresh and keep people from being bored with your voice,” said Stewart. “We were lucky to have the guy as long as we had him. In fact, one year we kept him because we hid his keys.”

The deal was made and announced in the spring of 2005: Stephen Colbert would host his own show starting in the fall. And Stewart’s Busboy Productions would serve as executive producers.

The first episode of The Colbert Report went on the air on October 17, 2005.

“It became so clear so quickly that it was going to work that it was kind of astounding,” said Comedy Central president Doug Herzog. “When the show debuted, I remember thinking that it had been birthed fully baked. That’s so rare. I don’t know if I’ve ever seen it before. The whole thing fits him like a glove. It’s really a virtuoso performance.”

“ The Colbert Report depends on Stephen’s ability to process information as this other person,” said Stewart. “Watch Colbert and it’s like the first time you use broadband: ‘How the fuck did that happen?’ He’s rendering in real time. He’s basically doing his show in a second language.”

After only eight shows, Comedy Central renewed The Colbert Report for an entire year.

For all of the critiquing and finger-pointing he was doing at the media and politicians, it turned out that in his private life—which he still heavily guarded—Stewart was turning into one big softy.

“When I look at Nathan, I think, I could kill someone for him. In fact, I could do it almost every day,” he admitted.

“I am a neutered cat, which is a very contented and warm feeling.”

IN THE SPRING of 2006, Stewart got his chance to perform in the ultimate stand-up venue:

The Oscars.

It was a controversial choice. For the most part, the celebrities chosen to host the annual awards ceremony are reliable middle-of-the-road stars, like Billy Crystal and Johnny Carson. In other words, stars who were considered safe, not automatically detested by a good chunk of the American public, and who wouldn’t run off the rails in front of an audience of up to 55 million people—the audience for the 1998 show when the movie Titanic attracted a record audience. Chris Rock had hosted the 2005 show, and viewership for the night had dropped 3 percent from the year before, going from 43.5 million viewers in 2004 to 42.1 million in 2005.

The Oscar producers also didn’t like the potential for political humor to disrupt the flow of the night—or for a host to unleash a few barbed zingers—and so the selection of Stewart was definitely a risk because they wanted to draw in more young viewers.

“You have to be humorous and able to prick the pomposity of it without coming across as mean-spirited or nasty,” said Damien Bona, author of Inside Oscar .

“It’s a lot of pressure; I’m very glad I’m not getting ready right now,” Chris Rock said in advance of the 2006 broadcast. “This time last year, I was losing my mind.”

For his part, Stewart tried to distract himself from the task at hand. “Free time is death to the anxious, and thank goodness I don’t have any of it right now,” he said.

Stewart fully realized the precarious situation he was in—as well as acknowledging the real honor—and so for the most part he played it safe. The most political joke he told was this: “I do have some sad news to report: Björk couldn’t be here tonight. She was trying on her Oscar dress and Dick Cheney shot her.”

The rest of the time, he stuck to the tried-and-true with quips like, “We’ve got movies about racism, prejudice, censorship, murders. This is why we go to movies, for an escape,” and “The Oscars is really I guess the one night of the year when you can see all your favorite stars without having to donate any money to the Democratic Party. And it’s exciting for the stars as well because it’s the first time many of you have ever voted for a winner.”

The critics were not kind. “It’s hard to believe that professional entertainers could have put together a show less entertaining than this year’s Oscars, hosted with a smug humorlessness by comic Jon Stewart, a sad and pale shadow of great hosts gone by,” said Tom Shales of the Washington Post.

The New York Times hurled the biggest insult anyone could at Stewart: “He wasn’t as funny as he usually is,” wrote the critic.

“He’s such a great performer and that’s what makes it so hard,” said his mentor, Caroline Hirsch. “That audience is an audience of performers, and it’s almost like they’re saying, prove it to me, make me laugh. And that’s hard to do. Doing the Oscars is a really hard gig.”

To be sure, the show didn’t get off to a great start. “The show began with a montage of previous hosts turning down the thankless gig, making Stewart seem like the last guy standing after a game of musical chairs,” wrote Gary Susman, a critic with Moviefone.com.

In his own postmortem, Stewart didn’t beat himself up over the reviews. “When you’re dealing with a group where eighty percent are walking home empty-handed, you want to make sure that when that night is over they don’t feel like they have just wasted twelve hours,” he said. “I actually didn’t think it was such a bad job.”

However, in the wake of the Oscars, some critics—and viewers—began to think that now that he was in his eighth year of meeting the grinding demands of The Daily Show, maybe it was time for Stewart to take a break, maybe look to something different and let someone else take the reins for a while.