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David Letterman, however, had noticed his show and saw a breakout host in the making. Dave’s production company, Worldwide Pants, offered Jon what was known as a holding deal: He would get paid; they would get access to Stewart’s clearly emerging talent. (And, conveniently, for a couple of years Jon would be off the market, just in case NBC fell out of love with Conan again and went looking for other late-night talent.) Surely somewhere a door would open a crack during this stint under Letterman’s aegis, and Jon would finally get a real chance to break through.

And so he did—but only tangentially thanks to Worldwide Pants. Jon actually got little out of his association with Dave’s company, apart from the occasional invitation to guest host Tom Snyder’s The Late Late Show. Given his availability to the Letterman camp, Stewart ought to have been teed up and ready to go when CBS, finally alarmed by Snyder’s sliding ratings and aging audience, sought a change. But when the Pants people went back into the host selection business, they passed over Jon Stewart again and decided instead that Craig Kilborn would be a better choice.

Kilborn, tall, blond, and jocky—he had played basketball at Montana State and made his name in television as an anchor on ESPN’s SportsCenter—was coming off a checkered run as the first anchor of the faux newscast on Comedy Central, The Daily Show. Created by two sharp, funny women, Lizz Winstead and Madeleine Smithberg, TDS quickly established itself as a clever nightly center for topical satire. Kilborn had won some fans with his wiseacre style, but he irritated an almost equal number. The show was a genuine hit by cable standards, though, and Kilborn might have settled in for a long run. But about a year in, he gave an interview to Esquire magazine in which he apparently wanted to underscore his masculinity, telling the reporter, “To be honest, Lizz does find me very attractive. If I wanted her to blow me, she would.”

Kilborn was suspended. Although he apologized, claiming he meant it as a joke, Winstead wasn’t amused—nor were many other women. The show had that hit thing going for it, however, and Comedy Central’s management thought better of letting Kilborn go. Only a year later, the Worldwide Pants organization sought him out to replace Snyder, though internally some members of Letterman’s company were appalled by the choice. Whatever his virtues as an on-air presenter—and Kilborn had a legitimate facility as a broadcaster—he didn’t seem to have a fraction of Stewart’s comedy talent or pure wit. And that magazine interview did not speak well of his judgment.

But Rob Burnett, the executive in charge of the Pants production unit, had his reasons for choosing Kilborn, which mainly had to do with Stewart’s being much like Dave and Kilborn’s being totally unlike Dave. (That was hardly surprising, given that Stewart was another young comic heavily influenced by Letterman.) On the face of it, having a talent with the potential to be the next Dave might seem like a recommendation. Burnett, however, viewed it as a problem. It would require, for one thing, that the show hire another stable of writers similar to the ones who worked for Dave, and to Burnett that seemed a tall order. When the Pants organization made the decision, Kilborn was also arguably better known than Stewart, which may have factored into the thinking. Another suggestion was offered by outsiders: Dave didn’t really want a guy playing immediately after him who might generate talk about succession. The quickwitted Stewart might have been good enough to do that; the preening Kilborn—some critics suggested it looked like he was doing the show in front of a mirror rather than a camera—was not likely to be any threat to Dave’s hegemony at CBS.

So another late-night opening suddenly closed for Jon Stewart. But his friends at the Letterman show had at the same time vacated another late-night chair. Did Jon want the job Craig Kilborn apparently thought