By Jeff Jensen
January 27, 2014 at 09:43 PM EST
Today Show

Jay Leno’s blitz of interviews in advance of his mandatory retirement from The Tonight Show reminds us that a graceful exit is hard to do — especially when people won’t let you.

Anyone expecting or wanting some sour chin music from the iconic comedian during his much-hyped appearance on Sunday’s 60 Minutes was probably disappointed. But it was tart enough, thanks to Steve Kroft’s decision to cast Leno’s story as a cultural flashpoint for a seismic generational shift, with aging baby boomers ceding/losing power to their kids and grandkids. CBS never accused NBC of ageism, but it used some choice factoids and soundbites from Leno to suggest that the network wasn’t doing right by its good and faithful servant, still the No. 1 player in late night. Following an intro in which Kroft cited research showing Leno to be the fifth most popular personality on TV and pitched his twilight-of-the-boomers premise, the piece proper began with Leno — jokingly — telling the story that he says he tells any newbie in the business, that the reason why showbiz pays so well is because “eventually, you are going to get screwed. That’s the way it works… That’s the way these things are.” No effort was made to define “it” or put “these things” in context (or ask NBC for comment) or what fairness looks like or should look like in an ad-supported business in which not all demographic groups are monetized equally. Leno might be the fifth most popular personality on television, but these days, that distinction comes with a trail of tiny little asterisks.

So began a profile that depicted a Leno trying to have it all ways. War-scarred victim. Thick-skinned team player. Relevant cultural icon. Contented soon-to-be retiree. Tireless entertainer. Everyman. Rich man. The only role he resisted was the one 60 Minutes wanted most — a Late Night King Lear, a sad and bitter old man who just doesn’t know when to quit.

Kroft’s piece doted on the “bizarre” “debacle” that was NBC’s first attempt to retire Leno from The Tonight Show at the height of his powers back in 2009 and replace him with Conan O’Brien. Kroft’s chronicle certainly flattered Leno, casting shade on the Team Coco narrative that Leno stole The Tonight Show back from him. Leno certainly appreciated this perspective (so did his wife, Mavis), as it mirrored his own. He was “blindsided”; it was like being dumped by a girlfriend; Conan acted unprofessionally. (I’m curious to see if and how O’Brien might respond to this interview.) During a trip to Leno’s airplane hangars, home to his legendary collection of vintage roadsters and muscle cars (Leno’s only extracurricular activity outside of his career), Kroft confronted Leno on his alarming lack of other interests and emotional growth. Leno balked, and a visiting Tim Allen squirmed. It was awkward for everyone.

If the big “get” here was for Leno to say that his current situation is completely analogous to his previous one and then swing away at NBC and Fallon, Kroft didn’t get it. Fallon, Leno said, is an “extremely qualified guy,” and he singled out Fallon’s ability to connect with audiences in ways that he can’t, like social media and viral video. When Kroft reminded Leno that he was similarly politic and good-sporty during the Conan ordeal, Leno evidenced surprise, then made an impish crack. “I did!? Well, we’ll see what happens.” Did 60 Minutes want to leave us wondering if Leno is rooting for Fallon’s failure? That he covets a third term behind The Tonight Show desk?

The loaded ambiguities of Leno’s 60 Minutes interview were clarified to some degree during a joint Jay-Jimmy interview with Matt Lauer on the Today show Monday morning. It was an excerpt from a longer sit-down that’s scheduled to air next week; NBC either wanted to capitalize on Leno’s 60 Minutes appearance with a next-day follow-up, or do some damage control, or both. Leno insisted that unlike the Conan situation, in which he was told he had to give up The Tonight Show, this time, with the Fallon situation, he was asked, and he agreed, and now, while he’d love to keep working, he is ready to leave. Fallon said he and Leno speak every few weeks, that Jay “roots for me” by praising his work. Both comedians said all the right things, although coming off the 60 Minutes interview, it was easy to question their sincerity.

It sucks getting fired from a job you love, regardless of how wealthy you are, and especially if you find your identity in your work, as Leno clearly does. Leno deserves a dignified exit — and Leno needs to put himself in a position where he can exit with dignity. If the 60 Minutes interview didn’t serve his interest, ultimately, that’s on him. NBC is not making a mistake in replacing him now, with Fallon. Leno is No. 1 now, but the late-night culture and business is changing and evolving; Fallon represents NBC’s best bet, at present, to transform The Tonight Show into the buzzy, transmedia entertainment enterprise that shows its need to be moving forward. Fallon represents the future. That’s a bitter pill to swallow if you’re Jay Leno. But he’s swallowing it. We shouldn’t be surprised if he winces while it’s going down.