By Jeff Jensen
Updated February 07, 2014 at 10:42 PM EST
Chris Haston/NBC

The Tonight Show

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Jay Leno said goodbye to The Tonight Show for the second time in his career on Thursday. Gone for good? So he joked. “I don’t need to be fired three times! I get the hint!” And so he wept, during his most personal — and arguably best — moment of his 22-year run as the custodian of the hallowed late night institution. “It really is time for me to go and hand it off to the next guy.” His last hour was a pretty good one, highlighted by the pure-pop moment of Billy Crystal bringing out a bunch of stars — Jack Black, Jim Parsons, Carol Burnett, Oprah Winfrey — for a snarky-funny ribbing of NBC for wanting Leno gone, or as the comedian put it earlier this week, in his sarcastic, self-serving way, “dead.” But those minutes, with Leno breaking down at his desk, were undeniably powerful. “This is tricky,” he said as he recalled how he lost his mother, father, and brother during the first three years of hosting The Tonight Show, and how the show and his work filled the void of a man suddenly without family, save for his wife of 34 years, Mavis. “This has been the greatest 22 years of life.”

It was a powerful exit for a man who loved his job and loves to work, perhaps too much, and who served his network faithfully if not always well, and vice versa. As affecting as Leno’s last bow might have been, the episodes that preceded the finale this past week represented a convincing argument that NBC needs a new suit sitting behind the desk, and a whole new creative sensibility in general.

To be fair to Leno, neither of his “retirements” have been easy pills to swallow, and not just because he remains a late night power player. The subtext of both: The future of The Tonight Show would be better served by a younger man. In 2009, it was Conan O’Brien; now, it is Jimmy Fallon.

It’s also hard to serve as both host to and guest of honor at your own weeklong farewell party. The measure of this complexity was the awkwardness that began each of his shows this past week. Leno emerged from backstage, greeted the crowd, and wanted to immediately launch into his monologue. But the audience — his fans — wouldn’t let him; they wanted to celebrate him with long, lingering ovations that Leno didn’t know how to receive. It was all he could to quickly get into tepid joke about how bad the Denver Broncos played in the Super Bowl. It makes sense. By week’s end, we would see, with his tears, the emotions he must have been holding at bay. Leno wasn’t ungrateful; he was probably just trying to hold it together.

Still, he radiated stiffness all week, and it cost him and his show some joy. When Matthew McConaughey visited on Wednesday, the actor told the story of his first Tonight Show appearance, and the advice Leno gave him to calm his nerves: “Just want to be here.” Leno failed to take his own advice during his swan song redux: Instead of engaging the moment, he resisted it, perhaps because he resented it. He finally acknowledged the subtext of the standing ovations in the Wednesday show, but with an off-the-cuff crack: “Where were you when I was renegotiating my contract? Where were you then?” He then hustled into a bit about the Seattle Seahawks. It was a confusing aside and transition. This is our fault? The audience that consistently made you No. 1 for two decades? Can you cool it with the lukewarm Super Bowl jokes so we can process this?!

The week was scattered with bitter cracks like that — the highest concentration of them during the Monday show, when Fallon was the marquee guest in a passing-of-the-torch moment that felt very “Let’s get this and you out of the way so I can move on with my week.” Some of these remarks I can’t begrudge, like Leno’s sarcastic intimations that he’s being put out to pasture because NBC think he’s “old.” Whatever the truth is, that’s exactly the perception, and if the network doesn’t like it, they should have tried harder to avoid it. For some reason, I feel offended for the man on this matter. Look, I’m not the biggest Leno fan. His stand-up and his traditionalist approach to the late night format doesn’t do anything for me. (Translation: I’m a Letterman guy.) He treated The Tonight Show as an entitlement, and then a happy habit, rather than a job and honor to be earned and won every single night. But all that’s irrelevant: I still feel NBC could have found a better way to show him to the door than to make him feel like a demographically undesirable liability. But that’s showbiz. And as Leno joked on 60 Minutes a couple weeks ago: That’s what the money’s for, right?

Other times this week, Leno came off as the poor sport, like his impish, passive-aggressive crack that “it would be a shame” if something unfortunate happened to his replacement during his visit, rendering Fallon incapable of performing his duties. Maybe I’m reading too much into Leno (see: “passive aggressive”), but what can’t be denied is that his potshots — while falling well within the tradition of late night comedians taking shots at their own network — weren’t the rim-shot winners he might have thought they were when he wrote them. They also fed the perception that tarnished him in the eyes of the media and the entertainment industry during the Conan debacle: that Leno was basically rooting for others — a fellow comedian, no less — to fail. Still, if we wanted Leno to be a man of grace in this situation, let’s be such ourselves: These jokes, however artless, simply tell us that Leno is really bummed to be leaving a job he loves, and/or can’t leave on his own terms.

I’m less forgiving of his interview with Sandra Bullock. She and McConaughey were his two bona fide superstar guests this past week. He made a big deal of these choices, both Oscar nominees; they were his picks for Best Actress and Best Actor, respectively, and he was using/abusing the privilege/power of his final week to tout them/showcase them. Leno couldn’t have been kinder to McConaughey. He showed careful respect for his work in Dallas Buyers Club, as well that of Jared Leto, and he set up McConaughey nicely to provide insight into his improvved cameo in The Wolf of Wall Street.

By contrast, Leno’s engagement with Bullock was embarrassing, for host and guest. The most charitable read of the segment was that Leno was trying to stage a chop-busting micro-roast, and perhaps Bullock knew some or all of what was coming. Even then, it all came out wrong, even sexist/misogynist. He jokingly called her a “crazy bitch” when talking with her about how she dealt with post-Speed fame (Bullock, taken aback, was left to quickly calculate how to roll with this and keep it light); then asked her about the long-forgotten fiasco that was Speed 2; then ran old tape of her mooning the camera while shooting Speed 2; then showed a montage of all the different hairstyles she’s worn during her appearances on the show over the years. He eventually got around to saluting her work, past and present, the way he saluted McConaughey, but still: Crazy bitch?! Yes, Leno was just goofin’. And I suspect Bullock gets Leno. We certainly know she can laugh at herself. But The Tonight Show needs a new-century host who’s a bit more in touch, and who is a bit more imaginative in the way he or she plays and banters with his or her guests.

Truth is, Leno was weak all week. His monologues were more scattered, punchless, and something-for-everyone wan than usual. His “topical” humor — the Super Bowl blowout, Brigham Young University’s bad attitude about banning masturbation, food poisoning on Royal Caribbean Cruise Line, Obamamcare — was uninspired. I can’t lie: the “funny headlines” bit always makes me laugh. Kevin Smith picking up his left-behind bong? Okay, clever. But a visit from Carrot Top? Not flattering to his brand.

Which is why I appreciated Billy Crystal’s appearance in the finale. His to-camera, stand-up salute to his friend may have been awkwardly staged, but his speech reminded us of the difficulty of the job: that Leno has been and can be quite funny, and that he has been a good friend to his audience. For a guy who hasn’t ever really been a member of that audience, it was a needed reminder and corrective. I also enjoyed their walk down memory lane, recalling their early stand-up days, and how Leno’s bachelor pad was the place to stay for comics visiting Boston. Crystal’s humanization of Leno got me thinking that Leno might have been better served over the years if he had a real co-host/sidekick — an Andy Richter, an Ed McMahon, someone who really knew him, who knew how to talk to him. It also made me think that Billy Crystal could make a heck of a Tonight Show host. Too bad NBC hates old people.

Watching Leno this week, I couldn’t help but remember the controversy that attended his anointment as Johnny Carson’s successor back in 1992. I think there are some who to this day have never forgiven Leno for getting a job that they think should have gone to Letterman. For those folks, The Tonight Show has been in limbo ever since, and Leno has been an epic placeholder for Carson’s true heir, someone who can lead the show — and late night television — into the future. Maybe this person will be Jimmy Fallon; maybe not. And so we join Jay Leno at home, with arms huffily folded, ready to pass judgment on “the next guy” — and ready to quickly uncross those arms and hold Leno back should Fallon fall.

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The Tonight Show

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