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Jay Leno's Last Show and Lasting Legacy: Saving a Tear for the Third Act

The comedian got what he always wanted -- "The Tonight Show" -- but at what cost? His ambition hurt his place in TV history and made secondary his stewardship of the venerable institution.

What He Will Miss Most
Austin Hargrave
Jay Leno

Jay Leno's second goodbye is -- and has been -- absolutely fascinating from the standpoint that it's mostly an irrelevant story. That's what happens when you leave -- no matter how you leave, it should be noted -- and then come back, before leaving again.

The fanfare is diminished. And in Leno's case, there's that added element of him having forced his way back in. It's messy and it ruins the narrative. Johnny Carson never did that. And Carson, for everybody currently playing the game, is the gold standard. For Leno, this will always be his legacy, whether he thinks that's fair or not.

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What is most fascinating to me is that Leno's universally agreed-upon greatest strength -- his tremendous work ethic -- is directly tied to the trait that many of his detractors (and friends) say is his worst: a need to be loved. Nobody gets universal approval for anything they do, but Leno has always seemed like a guy trying to get it every day of his life.

But on Thursday night, Leno's final night (that we know of) as host of The Tonight Show, he went out for the most part pleasing himself. He invited Billy Crystal, his first guest from his first show 22 years ago, to be his final and only guest. He invited Garth Brooks, a longtime friend and favorite, to be his final musical act. It's what Leno wanted, and there was something nice about seeing someone who tries so hard to please others do something for himself.

Of course, a television critic can't watch any of that without thinking (what to me is) the obvious: old-school classic in Crystal, mainstream American country in Brooks … welcome to your new demo, Jimmy Fallon!

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It was a strangely unemotional show until the final few minutes, when Leno teared up and said, "This has been the greatest 22 years of my life." First there was the standard Leno monologue, stretching past 12 minutes. "I don't like goodbyes -- NBC does" Leno said, his only direct knock about his departure. He also used the phrase "the worst part about losing this job" -- a string of words that, if you're still interested in reading the tea leaves, might say something telling.

Otherwise, Leno's last night was a parade of taped and live cameos: President Obama; Dana Carvey doing Leno; Matt Damon (an odd choice since he's a Jimmy Kimmel favorite); Tyler Perry; Mark Wahlberg, whose disinterest in giving Leno career advice was one of the funniest bits of the night; Martha Stewart poking fun at her persona and offering Leno a one-night stand if his wife, Mavis, ever gave him a one-time-only free pass; Fallon continuing his at-this-point wince-inducing genuflection routine; and a song-and-dance number from Crystal that featured Jack Black, Kim Kardashian, Carol Burnett and Oprah, among others.

It was as oddly retro as the O.J. Simpson joke in the monologue -- but in fairness, all rules and matters of taste shouldn't apply when it comes to a finale because a finale is personal. And whether it was Crystal calling Leno America's night light or Bob Costas, during a Winter Olympics segment that aired prior to the final show, saying that Leno was America's favorite based on the ratings (he was), the whole thing felt a little cobbled together. Yes, finales are like that. It's almost impertinent to question choices at such a time.

The show began with Crystal and Leno recalling their time together as unknown, make-it-or-break-it comics with no money and ended in real tears from Leno. Instead of something that went beyond thanking the people who worked on the show, he chose to quote Carson on his last show and say, "I bid you all a heartfelt goodnight." He then tossed it to Brooks to close the show with "Friends in Low Places."

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Just prior to the Carson quote, Leno acknowledged that Johnny was the best to ever do the job.

And yet, Leno's legacy -- which many critics will now try to sum up for a second time -- will always be tied to his infamous wheeling and dealing to assume Carson's coveted chair. That Carson preferred Letterman and stayed close with his rejected replacement through the years right up until he died (even writing jokes, in secret, for Letterman's monologue) is extraordinarily telling.

Johnny chose Dave. And from that moment on, after Leno got what he desperately wanted, there wasn't much change to the story. In fact, through the years it only got worse.

Leno hated being kicked out in 2009 in favor of Conan O'Brien -- and we all know how that ended, with NBC mucking that scenario up for years on end, from telling Leno he'd be out in five years no matter what because they had to pass the mantle to this kid Conan, to how badly the transition was handled, and again when the painfully ugly recoronation occurred and the Team CoCo term was invented. You may remember this period as the one periodically punctuated by Jimmy Kimmel pulling no punches in his disdain for Leno -- up to the now-legendary punking of Leno on Leno's own show -- or Letterman moving from the occasional eyebrow-raising snark about Leno to more regular, in-your-face bits of brutal honesty. The gloves were off.

Those were dark times marked by Leno getting back what he never wanted to give up in the first place. Getting back what he fought for so cloak-and-daggerishly before the Carson retirement. Yes, he remained the king on the coveted Tonight Show throne, but at what cost?

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Oh, that's easy. His reputation, and his legacy.

Yes, all of his friends have rallied to his side, including last guest Crystal. Jay's friends and supporters have been loyal. And by all (or most) personal accounts, why wouldn't they? Outside of wanting this one thing in real life so badly he'd do almost anything to get it, a good many people say that Leno is one of the nicest people they've ever met. Humble, dedicated, giving and really good at a lot of things. In fact, one of the things Leno has been best at is being the No. 1 late-night talk show host since he got the job. He's proud of that, as he should be. And he ultimately seemed, long after that early skirmish to replace Carson, the better fit for an older, more mainstream national audience than Letterman did. I would argue that, for both men, their fates led to the absolute best possible professional life. Letterman probably couldn't have invented and maintained many of his legendary bits and running gags, his love of dropping things off roofs or having such great video bits if he had immediately inherited the job from Carson. I think we would have seen a much less caustic, much less oddball Letterman -- and that's the kind of history I wouldn't want rewritten. And Leno was, in many ways, perfect for the very job he's succeeded at for so long.

He loved his monologue. He was absolutely a pushover with his guests. He had zero right angles. His safety guaranteed A-list stars, many who were wary of Letterman. Even when confronted with a situation where his disdain for contentious interviewing could have hurt him the most -- e.g., having Hugh Grant on post-hooker incident -- Leno hit it out of the park. It was his signature moment.

Leno was also great at doing silly stuff -- silly humor. The kind of "Can you believe this?" material that generated chuckles from the masses. He made his comedy mainstream (when, in the early days, it wasn't as gooey-soft as you might think from later history).

By far Leno's greatest achievement was coveting Carson's job so much that he protected it at all costs -- to the point of becoming the kind of nonincendiary bit of vanilla that Middle America went to bed with every night. In the very definition of broadcasting, Leno was a hero to the masses. He aced being benign.

You (and I) can't take that away from him. It will absolutely be part of his legacy. But, do you recall that aphorism about what the first sentence of your obituary will be? If you win a Nobel Prize, an Academy Award, a Pulitzer Prize, etc. -- it will be in the first sentence of your obituary. Disgrace yourself in some way, even if there's debate about its validity -- from Richard Nixon to John Edwards to Anthony Weiner; from "Shoeless" Joe Jackson to Pete Rose to Barry Bonds -- and that will be the first line of your obituary.

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Leno? He got what he wanted most in life, but there was a cost. From Carson to Letterman and O'Brien until this final departure, his is a reputation based on conniving and mistrust; of being the guy you had to watch out for when your back was turned. Relentlessly driven and with a need for approval that bordered on insatiable, Leno will always be the guy who wouldn't leave.

It's not his whole legacy. But the scandals of the departures and the returns, of the vociferous slams from peers, they will always be part of the memory -- large headlines in the history.

And it goes without saying -- except that it doesn't, because it can't possibly be unspoken -- this may not be Leno's last goodbye. Maybe that's why it was hard to feel emotional about his leaving. You always want to save that last tear for the right moment.

Email: Tim.Goodman@THR.com
Twitter: @BastardMachine