The War for Late Night Read online

  Soon the comparisons delivered by the Letterman camp took a different tack, such as “Dave is a four-star French restaurant; Jay is McDonald’s.” What Jay knew about McDonald’s was he liked to eat there occasionally, and that many more billions of meals were served there than at Le Bernardin. He would even make the analogy himself, describing his comedy as “good food at reasonable prices.”

  Still, Letterman mattered to Jay. Like no one else on television, no one else in show business, no one else even in his life, Letterman mattered. The two comics had been linked since their earliest days as stand-ups in LA; they also broke into television at about the same time, with Letterman opening the way for Jay to emerge into public consciousness by having him as the most frequent guest on his Late Night show.

  And of course they came together like estranged princes in a Shakespeare history play, each seeking to succeed the departing king. When NBC anointed Leno the host of The Tonight Show in 1992, it first played as a usurpation, as Letterman had for far longer been the presumptive heir. Later, when NBC came close to ousting Jay in favor of Dave, it turned into a Restoration drama—but only in one act. Leno survived, and rewrote the ending, but only at the cost of seeing his rival installed in the castle next door. And there they sat for sixteen years, separated by the narrowest of channels. Dave’s realm enjoyed a brief giddy reign before the size and strength of Jay’s historic empire of the night gradually overwhelmed him, leaving him permanently the lesser power.

  By 2005 the outcome was routine: Jay supreme; Dave suppressed. Mercurial and moody in the best of times, a perpetually frustrated Letterman tipped often toward maddening to both his always admiring but usually cowed staff and to any executives at CBS who came into contact with him. Apart from the big boss, Leslie Moonves, whom Dave grew to respect and would sometimes chat with playfully by phone on the air, network interaction tended to be minimal. Little good usually came of any request or suggestion from CBS. Letterman never deigned to try to enhance his position by making some effort to help out affiliates or cater to advertisers—no upfront appearances for him—and he certainly had no interest at all in speaking to the press, even when advantageous moments for publicity arose. Virtually every interview request was declined, unless there was an element of duty involved—paying back guests like Ted Koppel at Nightline, Regis Philbin on his morning show, or Oprah Winfrey on her afternoon show. To even innocuous appeals for his reaction to some development, significant or trivial, Letterman would tell his press representatives, “What I have to say I say on the show.”

  His tenth-year anniversary at CBS? No acknowledgement in the press. His twentieth anniversary as a late-night host—perfect fodder for some high-profile attention—received none. Emmy Awards won five years in a row, from 1998 to 2002? Dave didn’t show up to accept any of them and gave no interviews to express his feelings about them. The end of a famous feud with Oprah (she had resented his jokes about her) was marked by Dave’s publicly escorting her to the theater on Broadway next door to his own, where the musical she had produced, The Color Purple, was opening. While the stunt lifted the ratings for one glorious night, Dave had done no publicity to build up the numbers that night and he let the much covered moment with Oprah pass without taking any further steps to capitalize upon it.

  Sometimes his reluctance was based on his commendable commitment never to play the shameless showbiz shill in situations either intensely private or highly sensitive. So, talking only on the air about the life-threatening heart condition that led to serious bypass surgery in 2000—or even the bout with shingles in 2003 that induced him to call in guest hosts for the first time—became a matter of his personal integrity. And of course, Dave handled the most trying episode of his career—becoming the first entertainment voice to address the horror of the 9/11 attacks on New York and the nation—with such sensitivity and grace that he needed to do nothing else to add to his legend.

  By some sort of tacit agreement, everyone else in late night acknowledged that Dave needed to speak out first on the tragedy. On September 17 he brought his show back. Talking extemporaneously and from the heart, fighting his emotions all the way, Dave, in an eight-minute monologue from his desk, tried to put the reaction to the attack in some context. He praised New York’s mayor, Rudy Giuliani, and the city’s police and fire departments. He observed, “There is only one thing required of any of us and that is to be courageous, because courage, as you may know, defines all other human behavior. I believe, because I’ve done a little of this myself, pretending to be courageous is just as good as the real thing.” He ended with a salute to the city, saying that if anyone didn’t believe it before, they “could absolutely believe it now: New York City . . . is the greatest city in the world.”

  Letterman won unanimous praise for that show and the ones that followed, when he seemingly found just the right moments to weave some wit and comedy into the ongoing gloom. One NBC executive—speaking privately, because his opinion would hardly please the network’s own star—paid Dave the ultimate compliment: “Everybody looked to Dave for the way to do this. If there’s a Johnny out there, it’s Dave.”

  That was a comparison Dave himself would surely have disavowed; but it truly was only valid on the cultural level, not the ratings one. Johnny qualified as the all-time winner. Leno ranked as the current one.

  Jeff Zucker tried to underline that point in red. “There is no more late-night war,” he declared in 2003. There was only a victor and a vanquished—and NBC had the victor, no matter what Dave’s supporters in the media may have tried to argue. “I think the Letterman show appears more tired,” Zucker suggested, not caring if he drew a penalty for taunting. “I think it’s hard for the national media to accept the fact that Jay is so dominant. The national media has always been more drawn to the dark, brooding cynicism of Dave, rather than the populist wit of Jay.”

  How deep in Dave’s craw did comments like that stick? It was impossible to discern from the man himself, silent as always, except when he would let loose on the air with an occasional shot at Jay or NBC. (Every spring brought the Passover joke.) But Letterman did have someone to serve as his public mouthpiece: his executive producer, Rob Burnett. Long the most outspoken Letterman defender, Burnett, in the face of Jay’s continuing ratings superiority, returned fire from a subjective foxhole. “There are two parts of the so-called late-night war,” Burnett said. “One is: Who’s the best? That part of the war is over. Dave won.”

  Of course, that pronouncement was not going to stop people from keeping score. The stats had a different message: Jay was winning not only in the ratings but in financial terms as well. According to a cost analysis by the Nielsen ratings company, The Tonight Show in 2003 was able to charge about $65,000 for each thirty-second commercial; for the Late Show the price was about $53,000. Over the course of a year, that would add up to an advantage of tens of millions of dollars for NBC.

  Letterman, brooding up in his offices above Broadway, could not escape the box scores and balance sheets. Predisposed to kick himself unmercifully for even the slightest mistake or failing he perceived in himself, he punished staff members who disappointed him in less volatile ways, most often by stopping talking to them entirely. Few were ever fired—one exception had been his longtime executive producer Robert Morton, whom Dave dispatched in 1996 with unusual churlishness, declaring him to have been a “diseased limb”—but Dave’s silent treatment could go on for months, sometimes years. Even top producers, once put on ice, found themselves showing up for work but having nothing to do except continue to be paid.

  For his part, Leno never looked away from what Dave was doing. Partly, colleagues said, it was because Jay remained fascinated by Dave, his unpredictable nature, his whipsaw wit. But another part of Leno grew more and more astonished that Dave not only never seemed to pay a price for not making every effort to win, but was outright disdainful of the things Jay did routinely in his pursuit of quantifiable success.

  He couldn’t believe th
e attitude behind comments from the Letterman camp like one from Rob Burnett: “Jay runs The Tonight Show like a political campaign. If he thinks something will attract more viewers, he’ll do it. Jay sees that Arnold Schwarzenegger is hot, so he introduces Arnold at a political rally. He sees that wrestling is hot, so he wrestles for the WWF. Maybe Jay earned himself a few more viewers for doing those things, but you have to ask yourself: Who would you rather be? Jay or Dave?”

  Arrogance in the face of endless losing? In private moments, Jay could not help noting that Dave didn’t do that well anymore and wondering:. Where does all this power come from?

  But he knew the answer. Whenever Jay broke down the differing courses their careers had taken, Jay always acknowledged Dave’s great strength—on television. “I’m a comedian,” Leno said, analyzing their relative assets. “I’m not a talk-show host. I think Dave as a broadcaster is as good as there has ever been. I would say Dave is the better broadcaster and I am the better stand-up comedian.” He felt they had learned from each other. From Dave, Jay had learned to be a wordsmith. From Jay, Dave had learned how to be a performer and be aggressive and “hit the mic hard.”

  But faced with the change proposed by NBC in 2004, Dave didn’t factor much in how Leno parsed out his future. As he surveyed the changing late-night landscape around him, he considered the possible threats to his preeminence if he chose to dig in his heels and decline NBC’s proposed five-year plan. Say no, Leno reasoned, and he would be going up against Conan on Fox or ABC. “It’s not so much Conan—well, it’s Conan and it’s everything I’ve worked for in my career,” Jay said. “Conan would go to ABC, and then I would be fighting a war on two fronts. Dave . . . who knows what Dave was going to do? And whether Jon Stewart would step in for Dave, and then you’re fighting . . . two younger guys.”

  Jon Stewart? Nobody else seemed to be including him in the coming network late-night equation. NBC had not imagined any scenario that would have CBS turning to Stewart to replace Letterman, creating more viable competition for that younger audience they expected Conan to attract. But Jay had been a regular viewer of Jon Stewart dating back to a late-night show Jon had starred in on MTV. It seemed to Jay then that Stewart was reaching every possible person in his chosen demographic group (young, smart, hip) but no one else. It was obvious, though, that the guy was really funny. “You know, you never know,” Jay assessed. “Things come along; you never know what’s going to knock you out of the box.”

  As Jay peered over the horizon of his potential future, he saw a possibility that few others did: the cable guy who was coming into his own.

  Jon Stewart had been buzzing around the late-night airfield for years, usually landing on some auxiliary runway before taking off again in search of a better heading. He had tried out for the Late Night opening post-Dave with the rest of the stand-up community at NBCʹs showcase in early 1993 when he was thirty. Later the same year he successfully pitched MTV a thirty-minute late-night talk show. It only lasted a year but generated enough attention that Paramount stepped up and offered to syndicate it in an hour-long version. That, too, lasted less than a year.

  David Letterman, however, had noticed his show and saw a breakout host in the making. Dave’s production company, Worldwide Pants, offered Jon what was known as a holding deal: He would get paid; they would get access to Stewart’s clearly emerging talent. (And, conveniently, for a couple of years Jon would be off the market, just in case NBC fell out of love with Conan again and went looking for other late-night talent.) Surely somewhere a door would open a crack during this stint under Letterman’s aegis, and Jon would finally get a real chance to break through.

  And so he did—but only tangentially thanks to Worldwide Pants. Jon actually got little out of his association with Dave’s company, apart from the occasional invitation to guest host Tom Snyder’s The Late Late Show. Given his availability to the Letterman camp, Stewart ought to have been teed up and ready to go when CBS, finally alarmed by Snyder’s sliding ratings and aging audience, sought a change. But when the Pants people went back into the host selection business, they passed over Jon Stewart again and decided instead that Craig Kilborn would be a better choice.

  Kilborn, tall, blond, and jocky—he had played basketball at Montana State and made his name in television as an anchor on ESPN’s SportsCenter—was coming off a checkered run as the first anchor of the faux newscast on Comedy Central, The Daily Show. Created by two sharp, funny women, Lizz Winstead and Madeleine Smithberg, TDS quickly established itself as a clever nightly center for topical satire. Kilborn had won some fans with his wiseacre style, but he irritated an almost equal number. The show was a genuine hit by cable standards, though, and Kilborn might have settled in for a long run. But about a year in, he gave an interview to Esquire magazine in which he apparently wanted to underscore his masculinity, telling the reporter, “To be honest, Lizz does find me very attractive. If I wanted her to blow me, she would.”

  Kilborn was suspended. Although he apologized, claiming he meant it as a joke, Winstead wasn’t amused—nor were many other women. The show had that hit thing going for it, however, and Comedy Central’s management thought better of letting Kilborn go. Only a year later, the Worldwide Pants organization sought him out to replace Snyder, though internally some members of Letterman’s company were appalled by the choice. Whatever his virtues as an on-air presenter—and Kilborn had a legitimate facility as a broadcaster—he didn’t seem to have a fraction of Stewart’s comedy talent or pure wit. And that magazine interview did not speak well of his judgment.

  But Rob Burnett, the executive in charge of the Pants production unit, had his reasons for choosing Kilborn, which mainly had to do with Stewart’s being much like Dave and Kilborn’s being totally unlike Dave. (That was hardly surprising, given that Stewart was another young comic heavily influenced by Letterman.) On the face of it, having a talent with the potential to be the next Dave might seem like a recommendation. Burnett, however, viewed it as a problem. It would require, for one thing, that the show hire another stable of writers similar to the ones who worked for Dave, and to Burnett that seemed a tall order. When the Pants organization made the decision, Kilborn was also arguably better known than Stewart, which may have factored into the thinking. Another suggestion was offered by outsiders: Dave didn’t really want a guy playing immediately after him who might generate talk about succession. The quickwitted Stewart might have been good enough to do that; the preening Kilborn—some critics suggested it looked like he was doing the show in front of a mirror rather than a camera—was not likely to be any threat to Dave’s hegemony at CBS.

  So another late-night opening suddenly closed for Jon Stewart. But his friends at the Letterman show had at the same time vacated another late-night chair. Did Jon want the job Craig Kilborn apparently thought was second rate enough to move out of the first chance he got? Stewart had by this point signed a movie deal with Miramax, and while he did get a few cracks in films (most notably a campy horror comedy from Robert Rodriguez called The Faculty), the experience was enough for him to conclude he belonged on television.

  In 1999 Stewart accepted the anchor job on The Daily Show that Kilborn had abandoned—with just one week to prepare for his first appearance. It wasn’t network; it wasn’t after Letterman; it was even kind of sloppy seconds. But it was a nightly comedy show, with a bent toward news. Jon Stewart knew he was a news junkie, but more than anything else, he knew he was a comic.

  Comic came after busboy, waiter, bartender, mosquito sorter, and construction worker, among other temporary roles. Jon Stewart was not preordained to be funny onstage the way Jay Leno had been as a boy in Boston. Stewart grew up in Lawrenceville, New Jersey, near Trenton. He was Jonathan Stuart Leibowitz then, second child of an elementary school teacher mother and physics professor father. The family broke up when Jon was nine, and later jokes left listeners with the impression that Jon did not easily forgive his father. (As late as 2002, Jon told interviewers that his f
ather had never seen him perform.)

  Jon was smart and athletic, ending up at William and Mary, where he played left wing on the soccer team. His only real entertainment background to that point was some horn playing in the high school band. At loose ends after graduation, he fell into a succession of odd—and odder—jobs, highlighted by one that made a real impression: as a puppeteer for children with disabilities. That tapped at least obliquely into the latent streak of humor submerged in Stewart, and the experience inspired him to set out to try stand-up.

  It was a long and brutal initiation. Stewart spent close to a year working up the material—and courage—to appear at New York’s Bitter End club. When he finally did, he barely got through half the act before the flop sweat from the profound bombing he was delivering drove him from the stage—and almost out of the business. He stuck with it because at that point he wasn’t sure what else to do with his life.

  For two years he worked during the day as a bartender at a Mexican restaurant in Manhattan, earning just enough to live on so that he could show up every night at the Comedy Cellar and go on as the last act. Every weeknight, somewhere near two a.m., Jon Stewart performed before the drunk and the lonely of the New York metropolitan area. “I sucked for two straight years,” Jon would later tell aspiring comics, partly as advice and partly as storm warning.

  But slowly, incrementally, it came to him. Performing as Jon Stewart—he would later take the formal legal steps to abandon the name Leibowitz—he put on comedy muscle. His material got sharper, smarter. He landed some writing jobs, finally scoring a crucial gig hosting Comedy Central’s Short-Attention Span Theater. At around the same time, a young agent from William Morris, James Dixon, saw Jon performing stand-up. Sensing enormous appeal and potential in the obviously super-bright young comic, he signed him up. Much good—for both of them—would come from that initial connection.