The term “late-night wars” entered the vernacular in 1992, when Jay Leno and David Letterman ferociously jockeyed to take over The Tonight Show. The use of “wars” underlined just how dramatic the passing of the Tonight desk was in America: This was Johnny Carson’s stage, the one that allowed a host to talk to the bulk of America. The silly pulpit, if you will. The term has resurfaced every time there is unrest in the Dave/Jay hour, though by now its usage is purely ceremonial and habitual, as the real battle is elsewhere: Comedy Central and Adult Swim have been beating the broadcasters among viewers under 50 at least since 2011. But now, after 21 years, the war can be declared over, with NBC announcing Leno’s second (and likely final) retirement from Tonight, this time to make room for Jimmy Fallon. Because this is America, a victor will need to be declared. The Nielsen verdict will be decisive, of course: Jay has drawn more viewers (old and young) almost every year he and Dave have faced each other at 11:35. But history's judgment could be different. While he may have rarely worn a ratings crown, David Letterman will be remembered as the last true King of Late Night, the final legend of a TV genre – the network talk show – that is quickly going the way of the soap opera.
This is not to bash or demean or belittle Leno. (Sadly, he's done enough on his own to diminish his reputation, particularly with his continued insistence that he never agreed to turn over The Tonight Show to Conan O'Brien). Maintaining a lead over Letterman (and now Jimmy Kimmel), even as NBC's prime-time lineup has collapsed around him, is no small feat. By all accounts, he's been commendably loyal to his writers and staff, fighting as long as he could to keep their salaries high and jobs secure even as ratings for all the late-night shows plunged. And while Letterman almost never lifts a finger to promote Late Show, Leno has been relatively accessible to the media through most of his tenure, even showing up at NBC Entertainment chief Bob Greenblatt's Christmas party two years ago (not that Greenblatt appreciated that). I've talked to Jay a few times by phone, and will never forget the time, about fifteen years ago, when I was visiting Tonight's Burbank offices and Leno surprised me by popping into the break room … just as I was shoving a jelly donut into my piehole. (He didn't miss a beat, rattling off a couple jokes at my expense; it was awesome.) But the final judgment on Leno and Letterman has nothing to do with what kind of man either is. If it did, Letterman's Don Draper dalliances wouldn't help his cause.
Unlike with real wars, the history of pop culture isn’t written by the victors. The Wire didn't win anything when it was on the air: Emmys, ratings, or much respect from HBO. But five years after its last episode aired, the show is widely regarded as one of TV's best dramas ever and pops up as a pop-culture reference in everything from Salmon Fishing in the Yemen to Lil Wayne lyrics. Ratings rock star Two and a Half Men, on the other hand, only pops up elsewhere as a punchline. Dave has been a critical darling since his short-lived 1980 NBC morning show and cemented his legacy as a comedy innovator during the early years of Late Night. His refusal to lobby for Carson's gig cost him the Tonight job, but it also cast him as the underdog, the man who wouldn't play the corporate game. He mocked NBC execs on air, and later, at CBS, Les Moonves. It doesn't matter that Letterman has been every bit as money-hungry as Leno, repeatedly forcing CBS to break the bank during the 1990s and early 2000s to keep him happy or prevent him from jumping to ABC or Fox. Dave's a rebel, and we love rebels. We remember rebels.
Leno hurt his chances at leaving a legacy by opting to do a show that, almost by design, has been completely disposable. His Tonight had a couple sketch franchises – "Headlines" and "Jaywalking" — but neither is particularly inspired or enduring. The main reason he first jumped ahead of Dave in the ratings was because he focused on (and super-sized) his monologue, to the detriment of almost everything else on Tonight. It was a smart move for Leno for the near-term: Everyone watched Jay to hear his O.J. jokes, to see him skewer Clinton during the Lewinsky scandal. But monologues don’t stick in the mind. Making the first fifteen minutes of Tonight must-see TV was the right move for winning the ratings race, but it contributed nothing to defining Leno for history, except perhaps introducing his Dancing Itos. Johnny Carson’s monologue was also a core staple of his show, something no one missed. But his interplay with Ed McMahon and his frequent sketches were just as important: When you think of the endless tribute reels to Carson, you think of Ed Ames and the tomahawk and Carson doing Carnac, you don’t think of any of his jokes. Letterman too does a monologue, but it’s more obligatory: In the early years he would only do four or five jokes, and they served more as a parody of a monologue. In recent years it has grown longer, most likely because the notoriously rehearsal-phobic host seems no longer interested in innovating any kind of desk bit. But if you take a longer-range look at his late-night career, you can instantly fondly conjure many memorable moments, whether ongoing segments (Stupid Human Tricks, Viewer Mail, Will It Float?) or frequent guests with whom he had such memorable – and often confrontational – chemistry (Rupert Jee, Jack Hanna, Kamarr the Discount Magician). His recurring bits will linger because they were conceptual, not topical; Jay told jokes.
Ironically, another reason Letterman will be remembered as an icon rather than just a popular personality may be because he lost the Tonight gig: Dave has created two TV franchises from whole cloth, injecting both Late Night and Late Show with his comic DNA. Leno got to replace Carson on Tonight, but that condemned him to be caretaker instead of creator. Johnny's shadow hasn't hung over Jay for years, but that's mostly because the shadow faded, not because Leno established another enduring personality. I have no idea whether Letterman has finally shaken off the bitterness from not getting Tonight, but he should be forever grateful he "lost." That so-called failure forced Letterman (and his team) to build something new, taking his Late Night sensibility and amping it up for a larger crowd and bigger stage, free of worrying about whether they were honoring the history of Dave’s idol Johnny. And Letterman allowed CBS to finally be a competitor in late night. While NBC has been the late-night leader since at least the advent of color television, CBS was a pathetic also-ran for decades, trying everything from giving Pat Sajak a talk show (really!) to cheaply produced crime shows. Letterman instantly transformed the Eye into a late-night contender and opened up a profit spigot from which hundreds of millions in profits flowed for years. And while Letterman has had years when his relationship with CBS has been icy, for the most part, CBS has let Dave do whatever he wants, however he wants. It stood by him during the scandals and the heart surgery. And while Leno has now been battered and bullied by two different NBC regimes and forced to give up his throne twice, CBS has wisely said Dave can stay for as long as he wants. (In part, that's because CBS wisely realizes what NBC doesn't: There may be talk show hosts after Dave and Jay, but the replacements are likely to score lower ratings. Better to hold on to the legacy franchises as long as you can.)
It's quite possible that Letterman won't stay on when his contract expires at the end of next year. He may only outlast Leno by a few months. But it doesn't matter. The winner of Leno-Letterman won't be judged on how many years each man lasted, or who got the bigger ratings. It will all come down to who built a legacy. I bet it won't even be close.