Lisa Rogak - Angry Optimist

Executive producer Ben Karlin—in many eyes, Stewart’s anchor since day one—had been essentially running both shows since he assumed responsibility for the launch of The Colbert Report in 2005, and he had finally confessed he was wrung out from the schedule in 2006.

Plus, maybe the bigger sin was that after almost eight years of full-tilt production, it was simply a lot harder to come up with something funny. “You definitely get more intellectual about comedy,” Karlin admitted. “The laugh impulse has been deadened.”

Part of the problem was that The Daily Show was tried-and-true, while The Colbert Report was fresh and new, and though it was still finding its legs, the format and tone were so radically different from Stewart’s show that viewers increasingly opted to watch Colbert over Stewart.

One critic hit the nail on the head when he suggested the reason why The Daily Show was starting to feel like a chore. “ The Daily Show is like a really good marriage: solid, dependable, and deeply satisfying, but the mystery, wonder, and freshness are gone. I still think The Daily Show suffers from the absence of a Colbert or Carell. The Colbert Report, on the other hand, is like the giddy infatuation of new love. Anything seems possible. The sky’s the limit.”

And so while viewers who were inclined to watch both shows back-to-back may have had Stewart’s show on as background, as soon as 11:30 hit, they turned up the volume on the TV and really focused on Colbert. At that point, you never knew what he would do or say. The novelty of watching him introduce a guest and then run around the studio waving and bowing and accepting the audience’s raucous applause was still fresh. Plus, the caliber of guests he was able to attract was already leagues beyond Stewart’s: one night, Stewart interviewed Ben Stiller, while Colbert spoke with Peter Frampton and Henry Kissinger, both interviewed in his inimitable razor-sharp style.

“The jokes in each episode of The Daily Show now follow a rigid pattern,” wrote another critic. “Either they show a clip of a politician saying something stupid, followed by a cut to Stewart’s shocked/bemused expression, or Stewart has to deal with a fake news ‘correspondent’ who doesn’t quite understand what is going on in the world. While The Colbert Report could be weird to the point of incomprehensibility, it was at least surprising.”

Perhaps it was inevitable, but another problem with the Show was that Stewart’s particular brand of satirical fake news had begun to spread as traditional news programs started to ride Stewart’s coattails and began to adopt some of The Daily Show ’s characteristics. Keith Olbermann, who helped launch the MSNBC show Countdown in 2003, introduced a couple of segments in 2005 and 2006—respectively Worst Person in the World and Special Comments—which could have been lifted directly from a Stewart monologue, often poking fun and criticizing George W. Bush and Fox News. Soon, other news hosts and programs followed suit in both national and smaller markets.

Stewart was also picking some odd fights, and in a very public way. When he hosted financial expert Jim Cramer, host of CNBC’s Mad Money, on the show in the spring of 2009, both Comedy Central and CNBC played it up for the week preceding as being the fight of the century, or at least a good rollicking repeat of Stewart’s Crossfire appearance.

Essentially, Stewart accused Cramer and his network of complicity for misleading his viewers with inaccurate and over-the-top financial advice in the period before the economy began to tank in 2008.

“I understand that you want to make finance entertaining, but it’s not a fucking game,” said Stewart. “We’re both snake-oil salesmen to a certain extent. But we do label the show as snake oil here. Isn’t there a problem selling snake oil as vitamin tonic and saying that it cures impetigo?”

Instead of fighting back like Tucker Carlson had done, however, Cramer meekly nodded and agreed with Stewart’s barbs for the most part. “I try really hard to make as many good calls as I can,” he said. “I, too, like you, want to have a successful show. Should we have been constantly pointing out the mistakes that were made? Absolutely. I truly wish we had done more.”

While some critics—and many financial advisers—applauded Stewart for taking on Cramer, others had had enough of his good-guy tactics.

Regular fans were beginning to turn away. “Typically, I am a fan of The Daily Show, but I honestly believe Jon Stewart has taken a low blow with this verbal scuffle with Jim Cramer,” said one viewer. “Not only is it mean-spirited and unnecessary, but it’s not funny. And just as Cramer is paid to excite us about Wall Street, Stewart is paid to make us laugh. I wish he’d get back to work.”

Was Stewart getting tired? Was he getting so restless that he could no longer hide it? After all, it had been a decade since he had taken over from Craig Kilborn, who himself succumbed to complacency and predictability in the rigors of creating a new show from scratch four nights a week and had left The Late Late Show with Craig Kilborn just five years after ditching The Daily Show .

Though Stewart has never outwardly admitted if he’s been blocked—whether by a lack of creativity or by sheer exhaustion—he has said that the pressure of an insane deadline never fails to spur him on to finding just the right joke or new angle for a sketch.

Or maybe it was just the simple fact that he was so happy and content in his personal life that the pressure and crushing deadlines that he had to endure at the studio on a daily basis were getting harder to take. “When I’m in, I’m in,” he said.

He also had just become a father for the second time. Daughter Maggie Rose Stewart was born in February 2006, and though he had adjusted nicely to life with his son, he was a bit nervous about the prospect of dealing with a daughter.

“I don’t know that much about women,” he said. “A boy child, I feel like I’ll know how to deal with it if he has a problem. I’ll just be able to say to him, ‘Well, repress it,’ and hopefully he’ll swallow that, as I have. And then you figure you have thirty years before it comes out over dinner where somebody spills the gravy and then you’re like ‘I hate you!’

“But a girl, she’s going to want me to have tea with her and her panda. What am I going to do with that?”

To accommodate his growing family, in 2005 he and Tracey had bought a six-thousand-square-foot Tribeca duplex penthouse loft for almost $6 million through a real estate trust named the Shamsky Monkey Trust after his cat and dog. A few years later in 2008, Forbes would estimate his annual income at $14 million.

The loft quickly became his retreat from the world, and after the postmortem on the show wraps, he rushes out the door and heads downtown for home to see his wife and kids and animals. Most surprisingly, he turns into the polar opposite of his TV persona once he closes the door behind him. “He never talks about politics or world events,” Tracey said.

His sense of humor also morphs into something entirely different. “He’s silly, but it’s not like I live with a jokester,” she added. “He’s not annoying and not always on. Jon is not even that smart at home. He’s really all about his family.”

His dogs now included a new third addition, a three-legged pooch named Little Dipper. “The whole family can fit in one bed with three dogs placed strategically,” he said. “And the dogs are all pretty good about going under the covers and curling up. One nice thing is that it does generate a lot of heat. It’s like having one of those brick ovens that they make pizza in. The three of them get in there and it fires us up to thermonuclear levels.”