Anniversary shows are usually packed with video clips, fond anecdotes, and surprise visits from old friends. Yet Leno had something shocking in store for the half-century birthday of The Tonight Show on Sept. 27, 2004: He used the milestone to announce his retirement — in the year 2009. Despite his convivial statements about how ''the timing was right'' and there was ''no one more qualified than Conan'' to replace him at the desk, few in Hollywood believed that Leno — a tireless performer who does stand-up gigs all over the country when he's not taping — would choose to bolt when he had just won the ratings race for a ninth season in a row. More likely, Leno was edged out, especially since O'Brien, whose contract on Late Night was set to expire soon, had reportedly threatened to leave unless he was given the crown jewel of late night. The industry was in awe. ''They bought themselves five years,'' says the agent of NBC's succession plan. ''It was brilliant.''
Remarkably, NBC insisted then — and continues to do so — that Leno supported the transition plan. (Leno declined to comment for this article.) ''Jay acknowledged that he didn't want to have happen to his successor what happened to him back in 1992,'' says an NBC insider, referring to the cutthroat battle between Leno and David Letterman for The Tonight Show. ''It was also about going out on top. We pride ourselves at this company with smooth transitions, and we wanted this to be another one.'' For Leno, giving the five years' notice was a gentlemanly act, but it has allowed him a lot of time to reconsider the decision. Four years later, he continues to clobber Letterman — with an average of 4.8 million viewers to Letterman's 3.7 million, Leno is about to win his 13th consecutive season. Meanwhile, O'Brien is showing unexpected signs of vulnerability: CBS' Craig Ferguson has narrowed the gap among young viewers at 12:30 a.m., while Jimmy Kimmel has been grabbing the lion's share of buzz with his online video stunts. With 33-year-old Saturday Night Live vet Jimmy Fallon — a virtual novice — scheduled to move into O'Brien's Late Night chair, it's looking like NBC may have overplayed its hand. ''From a business standpoint, the last thing I'd want is the guy walking out the door, pissed at me,'' says one of several executives who will attempt to lure Leno away in November 2009 — the earliest the comedian can entertain offers. ''People like the guy and he's part of their routine. It's going to be tough for a lot of people [when he leaves]. If Jay presents himself as the victim, NBC will be hurt by that.''
Reversing the decision is possible, but at a formidable price. NBC would have to pay O'Brien more than $40 million in penalties if it reneges on its offer to give him the 11:30 p.m. time slot. But since decisions regarding The Tonight Show aren't made in fantasyland, NBC will likely try to keep Leno in the family by offering him alternatives. A 10 p.m. talk show that airs a couple nights a week (yep, in place of Law & Order) is one possibility; so is a program on one of NBC's sister cable networks, like USA or Bravo. Though NBC's entertainment co-chair Ben Silverman has publicly expressed pessimism that Leno will stay put, the network insider is more sanguine. He believes Leno simply won't be able to handle being off the air between the time he signs off of The Tonight Show sometime next spring (an announcement is expected soon) and January 2010, when his contract with NBC expires. ''He'll want to stay in the public eye,'' says the insider. ''Jay is a creature of habit. Part of our pitch will be that he gets to keep the same parking place, the same cluttered office. He likes that.''
Perhaps, but a better option might involve Leno backing one of his classic cars out of that parking space and hightailing it over to another network or TV studio. ''Absolutely, he should get the hell out of that joint,'' says a veteran late-night producer. ''He'll be richer than a sheik and he won't have to eat NBC's s---. What can they possibly offer him that he can do well? Nightly News? Dateline? Heroes?'' (We can hear the voice-over now. Next up on NBC: The showdown you've been waiting for — Leno vs. Sylar.)
NEXT PAGE: 'Honestly, I think if NBC went to Jay today and said, 'We're going to have to pay Conan $40 million to go away but we can't pay you a nickel,' he'd take it without blinking.''
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