Preview: Conan O'Brien's Tonight Show Debut

A changing of the guard on The Tonight Show is one of those rare television milestones that can't help but lead to commentary about the end of one era and the beginning of another, even in a case where the former host is not only not retiring, but is moving to a slightly earlier timeslot. Still, no host of the show has ever truly failed or been forced off the job on something other than his own terms, and NBC has been the frontrunner on weeknights at 11:30 p.m. for all but a few brief periods in the last fifty years, so the pressure is on for new host Conan O'Brien, who inherits The Tonight Show from Jay Leno beginning Monday.

On Leno's final broadcast last Friday, he and guest O'Brien reminisced about Conan's introduction to America as the new host of Late Night, which took place on a 1993 Tonight Show. O'Brien popped out looking utterly out of place, and addressed viewers in a nervous, high-pitched voice. From that very inauspicious beginning, O'Brien developed a comfort level with the camera and found a style that worked for him. During his tenure hosting Late Night, O'Brien gradually won over the nation's TV critics, including many who had quickly written him off as a disaster. By the time NBC believed it needed to designate a successor to Leno, O'Brien was the only real choice for the position.

But despite O'Brien's demonstrated skill in the 12:30 a.m. hour, there are reasons to worry about whether this transition will work as well as NBC hopes and expects. For starters, this will be the first time that a new Tonight Show host has ever faced more established direct competition on another network. David Letterman, who preceded O'Brien on Late Night and cast a shadow it took years for him to escape, is now the venerable veteran over on CBS, and while Dave has no particular reason to resent Conan, you know he would love to finally stick it to NBC after nearly fifteen years of being beaten soundly by Leno.

There is also reason to wonder if O'Brien, for all of the high esteem people hold him in, is really capable of meeting the high expectations NBC has for The Tonight Show. At the time Leno became permanent host, he had several years under his belt as Johnny Carson's designated guest host, and had not only proven he could handle the job, but shown that ratings would hold up with him in the chair. But O'Brien has not been a ratings juggernaut at 12:30, and in fact had been neck-and-neck for the last year with the less highly touted Craig Ferguson, host of CBS's Late Late Show.

Finally, no one can say for sure what the effect Leno's continuing presence on NBC, once his new 10 p.m. show starts up in September, will have on The Tonight Show. One school of thought is that the new format leaves O'Brien with the worst of all possible worlds: saddled with the expectations that come from hosting the most famous brand name in late night TV, but still playing second fiddle to Leno, who one assumes will get first dibs on the most desirable guests. In fact, since O'Brien is moving to Los Angeles from New York, he is in some respects less complementary with Leno than he once was.

What sort of show might we expect from O'Brien? The example of Letterman, who also made the move from 12:30 to 11:30, may be instructive. Letterman had only done a brief monologue when he hosted Late Night, but extended its length once he started on The Late Show. Likewise, O'Brien has not been famous for his topical monologues to this point, but Carson and especially Leno made them the centerpiece of The Tonight Show, so O'Brien will probably end up following suit to some extent. Also, Letterman cut back on the silly stunts such as throwing watermelons off roofs that characterized his 12:30 tenure once he took the earlier timeslot. How much of O'Brien's trademark frat-boy surrealism will make it onto the new Tonight Show? Conan has not aged as visibly as Letterman did during his time at Late Night (believe it or not, at 46 O'Brien has become the oldest person to ever begin hosting The Tonight Show), so expect a more gradual transition into "maturity."

The most obvious immediate difference between O'Brien and Leno will come via a revival of an old Tonight Show tradition that is also an old Conan tradition: the sidekick. Yes, Andy Richter is back at O'Brien's side, and while it's unfortunate that both of his worthy sitcom efforts were met with such indifference from viewers, his presence figures to lessen any nerves that Conan feels in the early going. O'Brien will have the use of a new studio on the Universal backlot, the first time The Tonight Show has moved since Carson brought his show west in 1972. And he has signaled that he intends to get a lot of mileage out of his own move to L.A., a major shift for the lifelong East Coaster and Harvard man.

O'Brien proved to be a much more versatile host than it first appeared he would be when he took over Late Night, and this ability to roll with the punches (who can forget the classic run of makeshift shows he threw together at Late Night during the writers' strike?) figures to be his best asset as he takes over one of television's toughest, but potentially most rewarding jobs.