Photo: NBC/Photofest

These are sunny, long-shadowed days in New York City; September is the deceptively glorious season of loss. The city is reborn but perhaps not quite rejuvenated: Our slightly weary-looking mayor is running for a third term, looking not so much like a raffish billionaire as late-issue Mayor Wagner. Our trademarked paragons of wealth and celebrity—Trumps, Hiltons, Diddys—seem either recession-worn or just a little silly. The valiant New York Times, gallant as a Rudyard Kipling regiment, is fighting for its life, waiting for the bugle calls of reinforcements or mini-payments. Wars grind on, the recession spits few gold coins, the one-woman ambition generator named Hillary R. Clinton is exporting her Lucy Van Pelt–like certitude to other nations, her replacement senator a genial mockery of the system. The Yankees are winning, that’s true, with a brutally efficient iteration of the team, but the long summer and the economy have draped gray through the town and even our lovely new mascot president seems careworn and drained.

But up on Broadway and 53rd Street at the Ed Sullivan Theater, a late-middle-aged man is leaping to work each late afternoon. These days, when David Letterman goes to work on his program and the lights go on, he bounds across the stage with the long goofy strides of a Dr. Seuss gazelle. The audience roars, and for one hour a day, the comedian is filled with hemoglobin and the sun shines upon him.

“Well, hi, folks!” he says. “Hello!” And then he snorts a little chuckle of hee-hee-hee in private, self-lacerating conversation with himself.

Four little words and a snort: marinated in history and sensibility, auguring the dread and pleasure that make up the little ongoing narrative of his life, the hour for which he’s paid $32 million a year. In a decade that has seen Tom Brokaw retire and Peter Jennings die, that has seen Carson fade from modern memory, David Letterman might be the last grown-up on network television.

The bad boy of Ball State, Huck Finn grown and weathered, David Letterman has become the national Daddy. He is the ideal dad for the age—not a particularly pristine dad, or full of Cronkitean certitude, but confused and serious and full of conflict, anger, and ambiguity. Letterman is not a fuzzy person; working live he gives off the kind of dangerous electricity of stripped, dangling power lines. But he is a fundamentally serious comedian holding onto the gig of his life—Late Show With David Letterman—the hour in his day that seems to give him purpose. It has never been better.

He has done the old Dave stuff and plenty of it—stupid tricks, top-ten lists, sending dogs off diving boards into a pool on West 53rd Street, hitting fungoes with Mark Teixeira, whacking tennis balls with Andy Roddick, goading guffawing audience members, wheedling a bob-haired, head-bobbing Anna Wintour, doing a nutty tango on marriage with the impressively bonkers Anne Heche, calling out Biff Henderson, accidentally spraying a pregnant lady on the sidewalk by remote-controlled hose, showing blown-up diagrams of the tick-borne disease he contracted in a tree house, indulging Renée Zellweger—but it has been something more.

These ought to be bright, sunny days of sweet victory for Letterman. He has run Late Show on CBS for sixteen years now, making a great deal of money for the network as its franchise player, and suddenly, he has been trouncing Conan O’Brien’s Tonight Show on a regular basis.

But on September 14, the game changes once more.

For anyone who cares, it’s the landscape on which two comedy adversaries do some twilight battle as the ancient world of network television fades. In a weird piece of television trigonometry, David Letterman will be taking on not only young Conan O’Brien but also, somewhat tangentially, his old Super Rival, Jay Leno, who—after fifteen years of generally chinning out Letterman at 11:35 p.m.—will be starting his new five-night-a-week strip show on NBC. The Jay Leno Show is a kind of inverted Tonight Show, with celebrity guests—beginning opening night with Jerry Seinfeld—front-ended by Leno’s monologue, with signature features like “Jaywalking” and “Headlines” news clips at the back end of the show. He will have a nightly monologue and also install a racetrack near the studio so that Tom Cruise can race around and break speed records. It will be American entertainment.

The Jay Leno Show is a huge risk for NBC and an epochal statement in the history of network television. Leno will be the first TV talk-show host to have a prime-time hour since Jack Paar did it Friday night at 10 p.m. in the early sixties. It is also a move that many have said augurs the end of prime-time network television as the main stage of American culture. Even if Leno succeeds triumphantly, he will have a difficult time averaging the almost 5 million viewers a night he had at The Tonight Show—compare that with the 40 million that ER once got at 10 p.m. on NBC—and an implicit statement by NBC Universal president and CEO Jeff Zucker that broadcast television is G.E.’s glorious old frigate and cable its main business: Zucker suggested that a 1.8 Nielsen among young-adult viewers would be a “home run.” That’s a tenth of what a ten o’clock show used to get on network television when TV was TV.

Photo: L-R: George Rose/Getty Images; CBS/Everett Collection; 2009 Worldwide Pants Inc.

Somehow, without anyone looking, David Letterman has superseded the usual TV categories of comic, or talk-show host, or broadcaster. He paces the stage at night worrying about the Afghan-election recount and generally free-associating about the flies and vultures flapping around in his head. His nightly broadcast from Broadway has become a weird and great American entity unto itself, a blurred throwback, an amalgam of the tradition he came from: Johnny Carson, Edward Murrow, Jack Paar. And the most middle-American of talk-show hosts has become the most New York–centric.

He is also an increasingly interesting human being who has absorbed, not evaded, events and recorded, not denied, human experience.

Craggy, bewildered, irascible Dave, with his gray crew cut, designer suits, and white socks—a nightly mind-blowing image in HDTV—has become a persona, a distinctive agglomeration of character traits, even more than his idol Johnny Carson, much more like Carson’s own idol, Jack Benny. His monologues are indifferent as one-liners and jokes, but the character who delivers them is one memorable American. He can reel off dozens of Obama jokes and McCain jokes and Paris Hilton jokes, but it is when Letterman begins to invert and mutter, when his personal neuroses and raw wounds are inflamed by the assaults of everyday life—and whose aren’t?—that is when he becomes something more than a good comedian and something like the scarred protagonist of his own comic novel—a bewildered, gutty mid-lifer at the crash intersection of American culture.

Who can’t identify with that?

Of course, he won’t cop to it. But for sixteen years, he’s been battling his archrival, Jay Leno. The Letterman versus Leno battle, while not as direct as the Late Show versus Tonight Show 11:30 skirmish—is still the most fascinating conflict on television, part Muhammad Ali versus Joe Frazier, two former kid comics, Carson acolytes turned old pros who know each other’s strengths and weaknesses, engaging each other once more, from an hour’s distance.

It is the itch Letterman can’t quite scratch. He has not let the NBC ten o’clock move alone in his monologues. “Spitzer is not only coming back,” he said last Tuesday night, “but they’re gonna give him the 10 p.m. slot.” Letterman has anticipated the battle with riff after riff denigrating the ten o’clock slot but with a scintilla of obvious envy.

As Dave has become a stripped-raw Jack Benny, Leno has become late Bob Hope, playing the State Fair audiences. “Cat jokes work,” The Wall Street Journal reported on him, as he tested new material in Boston this summer. “Edible underwear doesn’t.” His incessant shtick and weightless political attacks have made him a risk-free franchise. Of course President Obama visited his couch in Burbank. “I don’t like the edgy comics out there,” Deb Stoddard of Natick, Massachusetts, told the Journal. But she loves Jay Leno.

Twenty-eight years ago, I was working on a profile of David Letterman, a young, scruffy comedian who at that point had retreated west to Los Angeles after the noble collapse of his critically appreciated, under-watched 10 a.m. talk show. Letterman was considered the next big thing—NBC had decided to pay him a million dollars a year to wait for his next project. He and his writers were advocates of what they called “found comedy.” But suddenly he was lost.

He and I had just gone to the Improv in Hollywood and watched a lot of stand-up acts work. When we came out, he looked down the street and saw a comedian with a spiky wave of black hair and a high whine of a voice surrounded by other comics.

“That,” said David Letterman, “is the funniest stand-up guy working.”

It was Jay Leno doing an ad hoc routine on the street corner: Pat Cooper, the great malevolent Vegas comedian, had been on Tom Snyder’s late-night show the night before and attacked Cher, Tom Jones, and Tony Bennett frontally enough to make sure he would not work west of Allentown, Pennsylvania, for a long time. Leno pantomimed Pat Cooper taking out a razor and slitting his wrists and his own throat as he gave the interview.

It was deeply, viciously funny, and Letterman was floored by it. But neither he nor Leno could have known at that moment that it was a predictive moment and a cautionary one. In the years following, Leno took The Tonight Show and, after a bumpy start, sailed above and ahead of Letterman’s Late Show on CBS to become the processed food of American comedy.

In 1982, Letterman got the 12:30 a.m. slot at NBC and changed American comedy. Leno, meanwhile, became not the King of Late Night as Carson had been but a kind of Viceroy, a holding pattern that became a habit and then a long-term habit, benign and risk-free. He seemed genuinely nice—he once compared himself to Old Fezziwig in A Christmas Carol—building a success but rarely flooring it with the show. He was, he liked to say, a “big-tent guy.”

When NBC and Carson Productions gave Letterman his show, they believed they were establishing another NBC star; they didn’t understand that they were laying the groundwork for a pervasive culture of irony. Letterman’s program created a sensibility that permeated TV, movies, literature, music, art, and magazines: The ceaseless joke of cultural debunking became the surgical tool that guided a generation of college students to strip the showbiz skin of the past 50 years. Letterman played disgusted consumer and truth teller; “Oh, that’s good,” he would say. Or occasionally just, “It’s crap, ladies and gentlemen!”

Long before he took Zsa Zsa Gabor to fast-food restaurants, he hauled out an actor named Calvert DeForest to play Larry “Bud” Melman as a kind of affectless piece of human tofu in the Letterman soup, reading his lines atonally and playing Santa Claus to slightly horrified children. In 1985, he made an enemy of Bryant Gumbel by turning a bullhorn on an outside taping of the Today show. Letterman established himself decisively on April 8, 1986, when he turned up in the lobby of the G.E. Building with a fruit basket to meet NBC’s new owner and was thrown out by security. He became the voice and the face of affectionate disaffection, so that when, six years later, Carson retired, NBC anointed not the scruffy jester but the smoother ward politician, Jay Leno—a man who could be counted on to work the affiliates.

As you know, Jay Leno got the gig and delivered.

But the choice hurt Letterman deeply: When in 2000 he had quintuple-bypass surgery and returned to work after five and a half weeks, one of his first jokes was, “Bypass surgery, it’s when doctors surgically create new blood flow to your heart … A bypass is what happened to me when I didn’t get The Tonight Show.”

David Letterman has become the national daddy—not a particularly pristine dad, or full of Cronkitean certitude, but confused and serious and full of anger and ambiguity.

Nevertheless, a lot of his pain was self-inflicted. He moved three blocks west and three blocks north from Rockefeller Center to the old Ed Sullivan Theater, which CBS renovated for him in 1993 and where he had a short period of intense success and then a long period of mild self-destruction. At first, he could do no wrong on CBS. Every joke hit, and he was trouncing The Tonight Show. But then some mysterious mechanism kicked in, as though he could not endure his success. From a beautifully tuned machine, the springs popped and it seemed to bottom out on a strange night in which he began literally beating the stuffing out of a David Letterman mannequin onstage.

Then something amazing happened to David Letterman, some weird combination of history and biography that moved him from a distinctive oddity of American comedy to something that came strangely close to greatness. It may have happened in three spasms of event.

One thing was his heart surgery elicited a depth of emotion from him that few suspected he had. The night he came back, he looked cadaverously—almost dangerously—thin but throbbingly exuberant. The irony had departed, as had his emotional detachment. Letterman still wasn’t sentimental, but he seemed suddenly grateful for both his life and his gig.

Another was his return to the air on September 17, 2001; he was the first entertainer back on, and his extemporaneous, husky-voiced monologue was a landmark in broadcasting. “As I understand it … we’re told that they were zealots,” he said that night, “fueled by religious fervor. And if you live to be 1,000 years old, will that make any sense to you? Will that make any goddamn sense?” It also fused him to New York City.

The third may have been this year. It was the year in which he had a protracted political participation, bringing the Republican nominee for president, John McCain, to his couch in contrition for having lied to him, the year in which he drew the mad ire of Sarah Palin of Alaska for a sloppy burlesque joke about her daughter for which he has performed a kind of anti-contrition after Governor Palin’s attempts to somehow stitch Letterman to the Eastern Media Establishment and to knit it into a combination of conservatism and feminism. He apologized immediately, but his long recoil has been a giddy froth of nightly retribution. And he does not appear sated.

“At one of these town-hall meetings,” Letterman said August 27, pacing back and forth, “McCain had to have a crazy woman removed by security … And I’m thinking, well geez, he should have done that a year ago.”

It didn’t reek of self-righteousness; he seemed to be protecting his program like a frontier landowner with a rifle. He wasn’t wrong—the right wing was getting ready to light bonfires and demonize him. There actually was a Fire Dave rally. Maybe it wasn’t a good idea to say that Sarah Palin’s daughter had been knocked up by Alex Rodriguez during the seventh-inning stretch. The first night of the controversy, he said, “You know, this very well could be my last show. I don’t know why we all find that amusing.” Then later: “Would I do anything to advocate or contribute to underage sexual abuse or misconduct? Absolutely not. Not in a thousand years! Look at me. Do I look like I’m trying to make trouble?”

He looked genuinely, deeply upset. A couple of days passed. CBS affiliates roiled and yahoos wrote to Les Moonves. Letterman made a second apology more gauged to the affiliates. When Sarah Palin grudgingly accepted the apology, she did it through Fox News.

But he snapped back. He seemed to compensate with a new onslaught of Palin jokes, then back to Dick Cheney for a comfort stop. Mostly he had just entered some stage of his career as a kind of crabby eccentric, complaining about his new wife’s friends, setting up tales of sleeping in the tree house with his 5-year-old son, Harry, and picking up a virus that brought him into work for four nights with a 103-degree fever. He put himself in a video triptych with Regis Philbin and Larry King as the three oldest men in TV. He imagined being elder-abused by subway bullies and imagined the distaste with which his open-heart-surgery scars would be viewed on the beach.

He had become something out of James Thurber or Twain, a satisfyingly complete humorist, telling satisfying character tales that didn’t seem to have an endpoint. His pursuit of dinner with Barack Obama and Oprah Winfrey on Martha’s Vineyard spanned many nights, epic in its statement of Dave’s injury. “Oprah—a national treasure,” he said, looking us straight in the camera. “Me—a … guy with a television show.” A look of confusion and hurt narcissism filled every crevice of his 62-year-old face. “I’ll tell you what I’m going to do, I’m going to borrow a busboy’s uniform and find out where Obama and Oprah are eating dinner and then … ” He pantomimed carrying the tray over to the table where they were eating, sure that he would then be invited to sit down with them. Later in the week, he insisted that the Secret Service had banned him from the entire island and that he had to explain it to his son Harry, who had his heart set on a shell-seeking vacation.

Jack Paar used to do something like this on The Tonight Show in the fifties, the program that personalized and revolutionized late-night television. Paar would shock and delight his audience with his persona—stuttering and assuring them by putting his hand on his chest, “This is true, I swear, I mean I could not make this up. I kid you not”—then telling a story about his daughter shopping for a training bra or what he thought of Fidel Castro, or he would self-flagellate his own neurotic inability to negotiate modern life. Johnny Carson—mentholated and surgical—followed Paar in 1962, and it was he, of course, whom Letterman idolized. Finally, Letterman had merged Steve Allen’s absurdity, Jack Paar’s neurotic confessionalism, and Carson’s topicality.

The Conan part of the battle is easier. Dave has become the tenured Ol’ Professor of American comedy, and Conan O’Brien, brilliant and delightful as he is, seems to be playing the graduate student. On August 31, as Letterman was sending dogs off a diving board and running through a bramble bush of madness with Howie Mandel, Conan was struggling manfully with the deliriously funny but audience-inscrutable Norm MacDonald, who had silenced his audience by performing a cruel mockery of Jay Leno’s “Headlines” routine, the deadness of which was the joke itself. O’Brien, on his magnificent new set in a beautiful new suit, was almost breaking a sweat and visibly exhaled when the segment was done. Over on CBS, Dave was giggling and whinnying away.

It’s a late-inning victory, but apparently Letterman is incapable on some level of believing it or accepting it. And the numbers are not unambiguous: Dave is winning significantly, but he seems to be the King of Geezer Nation; Letterman is beating Conan by close to a million viewers in the Nielsens despite O’Brien’s legitimate demographic claims. Conan has time on his side. Letterman will almost certainly hang it up at the end of this contract. He’ll be 65 in 2012, and Carson hung it up at 66 in 1992.

When he does, he will have been on late night for 30 years, the same length of time as Johnny Carson. When Carson died, David Letterman gave the classiest tribute to the man to whom he said he owed his career, an elegant Viking funeral. He came out onstage and did his monologue brilliantly, squeezing it for each laugh he could, returning to the desk and eulogizing his mentor. He then told the audience—separating the laughs from the attendant sentimentality—that each joke he had told had been written and submitted to the show by Carson himself in the previous months. He may have been losing to Leno in the ratings, but he K.O.’d him on lineage.

In 1895, Mark Twain, another dapper crabapple discoursing on politics and society, prepared a worldwide lecture tour that he began in New York City—actually using inmates at Randalls Island House of Refuge as his warm-up audience. A little like Letterman complaining about Oprah and Obama, in a modern nod to the coming new century, he planned to put up photos of all the celebrities who had decided not to show at his first lecture: General Sherman, General Lee, Gladstone, and Disraeli. “Every one of these illustrious men was sorry, and sent regrets; even lamentations.”

Then the speech went: “As soon as a man recognizes that he has drifted into age, he gets reminiscent. He wants to talk and talk; and not about the present or the future, but about his old times. For there is where the pathos of his life lies—and the charm of it.”

David Letterman has hit the part of life where he wants to talk and talk. But he seems to be still speaking of the present and the future. He is 62 and has chosen not to drift but to floor it, a boy of autumn, Huck Finn in September, the last American codger, the crabby voice of American reason, heedless, uncompromising, and driven. Long may he chortle.