The War for Late Night

by Carter, Bill

  When Debbie Vickers arrived hours later, she would take a reading of Jay’s demeanor. Most days she could discern the familiar attributes: steady, purposeful, joke obsessed. It didn’t mean Jay was no longer feeling the disappointment, resentment, and regret that NBC’s long-range termination notice had planted inside him. It meant only that, for the moment anyway, he was living by what he called “the first rule of show business: Don’t create anything bigger than your act.” Jay interpreted the rule to mean that, if you found yourself consumed by something bigger than what you are known for, your downfall was assured. If something distracting or dispiriting was going on in his life, his duty was to shrug it off, get back in the game of telling jokes, and be funny, day in, day out.

  But after those initial six months passed, Vickers knew that every day would no longer be conventional. There came a morning, and then several mornings, when Jay’s demeanor was clearly different: sullen, chagrined, joke obsessed. On those days Leno would unburden himself to Vickers, spilling out his undissipated confusion over NBCʹs decision. His unhappiness was only exacerbated if he played a gig somewhere and faced bewildered fans asking, “Why are you retiring, Jay?” He would try to laugh it off, tell them of course he wasn’t really retiring, he would still tour and be around plenty. But the exercise was excruciating. So was having to deal with the guests who brought up the subject on the air, with cracks about being put out to pasture or some other dopey expression.

  “I’m just sick of lying,” Leno told Vickers.

  On the bad days he would openly kick around his options. At worst, he would announce, he would end up a really rich person. Or he just might decide to defect; maybe he would go down the road to ABC. They might be interested in him over there.

  That was the scenario that eventually filtered back to Rick Ludwin from his contacts on the show. In his capacity as supervisor of late night for NBC, Ludwin always spent a great deal of time around the Tonight studio, but Jay wasn’t sending a message to NBC about his litany of unhappiness through Rick—maybe because Jay had begun to suspect that Ludwin had been one of the architects of the Conan elevation.

  Inside the confines of the Tonight Show world, Ludwin heard Jay had been telling staff members things like: “Instead of getting off the freeway off-ramp for Bob Hope Drive and turning left, we’ll just turn right and go up to the Disney lot on Buena Vista. We’ll take the whole staff and just move on up to Disney and ABC.”

  Ludwin would dutifully report back to his management about Jay’s prospective driving directions. The news didn’t really surprise anyone; Ludwin and the others at NBC hardly expected Jay was going to pack it in and take up gardening.

  Jay’s message could also come through at times in his monologue. More jokes began to appear about NBCʹs expertise in coming in fourth in the network rankings. A failure by a politician or sports team in the news somehow led to comparisons to NBC. When he returned from a dark week and NBC had done some redecorating on his stage, including installing a new desk, Jay feigned surprise, saying, “It’s not like NBC to get rid of something that’s worked perfectly well for fifteen years.”

  When Brett Favre of the Green Bay Packers was let go by his team after long years of exceptional play, Jay remarked, with an obvious edge, “His bosses don’t want him anymore—even though he was doing a really good job.” Later, during the 2008 presidential primaries, Jay went through the news of the day, which included a story about Hillary Clinton’s camp making a secret offer to Barack Obama to run with her as vice presidential nominee. Jay’s joke: “Obama is wondering why he’s being offered the second position when he’s still in first place.” Pause. “I’ve been wondering the same thing myself.”

  And occasionally Conan would get a pointed reference, as in one holiday-period show when Jay turned to his bandleader, Kevin Eubanks, and asked, “Kev, you ever regift?” (Pause.) “I do. I regifted; I gave Conan something I got fifteen years ago.”

  At least Jay could derive a little cathartic satisfaction from nailing NBC with a good shot every once in a while. It was fun for him—in a small way. But it wasn’t as though it was going to make any difference. Leno had resigned himself to the fact that nobody was going to reverse the decision. The NBC executives were hardly going to change their minds.

  In meetings of his entertainment group, Jeff Zucker enjoyed putting people on the spot, usually in jest, though for the most part the executives under him never really believed he was kidding. When late night was being considered, Zucker truly was only needling his executives through 2005 and 2006, raising questions about how things were shaping up. He was feeling no regrets. Profits were still pouring in from both of his hour-long shows, profits he had protected by locking in both stars; ABC and Fox still weren’t in the entertainment game in late night. All seemed right in that world.

  But as the years rolled by, with all the players back on their isolated islands, the endgame, once a blip on the horizon, began to come into focus, gather shape—and the shape looked dark and smoky, like a distant storm.

  Zucker, whose prime-time headaches had gone from annoying to chronic to blindingly intense, now had to endure a faint but growing buzzing in his ear: the sound of Jay Leno humming, “Na, na, na, na. Na, na, na, na. Hey, hey, hey, good-bye.”

  So as 2006 rolled into 2007, Zucker began calculating what losing Jay Leno might really mean—especially if he landed in the late-night arms of a competitor. Zucker, an eye on the long-range calendar, began foraging for kernels of ideas that might grow into a feasible possibility to keep Jay attached to NBC in some capacity.

  So Zucker, whenever he dropped in on his entertainment staff in Burbank, running the meetings as always, had sharpened his late-night focus. He would turn to Rick Ludwin, employing his usual half-puckish, half-pointed tone.

  “So, Rick, how’re you sleeping at night?” Zucker would ask, and then scan the table, letting the group know how playfully pregnant the question really was. Ludwin, looking bookish as usual, was flanked almost always by his late-night deputy Nick Bernstein, so boyish next to the much taller Ludwin that they were affectionately known as Batman and Robin. Ludwin had a ready answer: “Like a baby.”

  The cause for Zucker’s concern about the degree of Ludwin’s restful-ness was no mystery to anyone at the meetings. Jay was still winning handily; Conan was . . . well, doing fine. Rick—backed by Nick—never backed down, never wavered in supporting Conan’s ascension to The Tonight Show. The two NBC late-night executives had complete faith in OʹBrien and were willing to defend that faith against any doubters.

  In these meetings doubters had begun to speak up with questions about Conan, and they always sprang from the same concern: Should we worry that he’s a little too narrow, a little too hip, a little too New York, a little too young male college guy and not enough middle America, middle age, middle brow?

  Ludwin always went to the same place to answer the doubters. The Conan you will see on The Tonight Show is that guy who stood up on that stage at the Emmy Awards and charmed people with broad, easily accessible humor. Conan went into the Emmys with the intention to entertain not only the audience in the Shrine Auditorium but the millions more watching at home. He killed doing bits that were all Conan, bits that pleased his hard-core fans and yet didn’t require newcomers to know any of the backstory to get the comedy. He would do the same at eleven thirty, Ludwin promised.

  His stout defense may not have swayed everyone at the meeting, but it certainly did persuade them all that Rick Ludwin had strength in his convictions—and he was unalterably convinced that Conan O’Brien was the right guy at the right time for NBC.

  If they had had a vote, a group of television executives from the other networks would have happily stumped for Conan as well. To the hierarchy of ABC and Fox, NBC’s move had the look of a free ticket on the late-night gravy train. Were they really going to usher the dominant late-night star out the door? And leave him open to sign elsewhere, bringing along the $50 million to $100 million in prof
its that had previously gone to NBC? Was there a catch?

  Maybe. It would certainly take strenuous wooing to land Leno, who was famous for his reluctance to change any habit (like those denim shirts and Payless shoes), never mind one as big as whom he would work for. And there was that ungodly long wait. Who knew what NBC might pull in the end, if it really looked as though a competitor was about to grab Leno? Still, it was surely worth trying.

  ABC still had its Nightline issue, but the network had shown its hand in 2002 when it chased Letterman. For the right talent the 11:35 hour would be offered up, no matter how loudly the news division might howl to the moon (and the press). Leno was clearly the right talent. It went beyond a no-brainer; if ABC didn’t pursue Jay, the Disney shareholders would have a right to sue them for malfeasance. Bob Iger, who had been named chief executive of Disney in 2005, personally took charge of supervising the Leno courtship, with help from Anne Sweeney, the top ABC corporate executive, and Steve McPherson, the head of entertainment.

  Over at Fox, Peter Chernin, still eager to fill the network’s late-night void, might still have preferred Conan, in terms of matching the sensibility of his network. But how could any network pass on the opportunity to sign the biggest dog in the yard? How could Fox stay on the sidelines? Chernin decided again to head up the Fox effort to lure away an NBC late-night star.

  Fox’s hunger to grab a slice of late night had not abated since the disappointment of failing to land Conan in 2001. The network had sniffed around for other potential candidates, and in 2007 made a full-frontal assault on what it considered to be a potential game-changing name in late night when Chernin and Fox took a serious run at Billy Crystal.

  The well-respected comic, whose already soaring career went stratospheric thanks to his eight-time much-celebrated hosting performances at the Academy Awards, had not previously been part of the big late-night derbies. With movies, one-man Broadway shows, and Oscar duties, Crystal hardly needed the profile boost of his own talk show. But when Fox came calling, he listened.

  For one thing, Fox presented a compelling case. It had put together a PowerPoint presentation of what it called a late-night deck, which broke down what the comic could expect in terms of station clearances and advertising sales, and even a guess at what size audience might be available. (Once again, the pitch was to launch a show at eleven p.m., giving Crystal a half-hour jump on Leno and Letterman.) And then there was the $20 million-plus potential payday.

  The Fox executives were convinced they had gotten close, really close, to making a deal with Billy. He asked all the right questions; the interest was there. But if he hadn’t already been aware of just how much effort went into these jobs, having done the late-night rounds himself—including, famously, being the first ever guest on Leno’s Tonight Show—it hardly took much due diligence to learn. “When Billy found out how much you have to work,” said one Fox entertainment executive, “he thought, No way.”

  Workload was never going to be an issue with Jay Leno, of course, whose reputation preceded him. The product might not always be fresh or exciting or new to the critics, but it was going to be pumped out on a regular basis and it was going to generate numbers—and dollars. NBC’s competitors knew if they somehow could lure Jay away, the tectonic plates in the late-night world would slide and shift with devastating results.

  But the rules had to be observed. NBC held exclusive rights to Jay Leno’s television work for the full period of his contract. That meant that any flirtations that went over the line into an actual pass—as in, anything resembling a real offer of future employment for Jay elsewhere—would be grounds for a legitimate claim of tampering, or tortious interference, if it ever got to court.

  Hollywood deals generally hold only loosely to such legal niceties. Agents and managers test the waters of future associations for their clients all the time, and studios and networks have their ways of letting talent know how much they love the idea of getting together someday. Everyone in the late-night game remembered how David Letterman’s team had handled his contractual complications with NBC when the star looked to flee in 1993. Though bound by limitations stipulating when Letterman would be free to negotiate any kind of new deal, his agents at CAA simply told suitors to make their best pitch—and all Dave would do was listen.

  Now Leno found himself in a similar position: He was all ears.

  The approaches from ABC and Fox were general at first. Interest was conveyed; discreet conversations were held. Everyone understood the terms. Jay was locked in at NBC through January 1, 2010, and NBC retained exclusive negotiating rights with him until late November 2009. No outside entity could engage in any negotiation with him before that time. Jay, of course, had no formal representation, so the only way to get to him was either directly or through his lawyer, Ken Ziffren. Quiet though it was, none of this activity caught NBC by surprise in the least. “I expect Bob Iger and Peter Chernin are camped out at Leno’s garage,” one top NBC Entertainment executive said.

  If they were not there exactly, they were certainly cruising the neighborhood. And if NBC didn’t get word of Jay’s courtship some other way, Leno had his own means of communication—like the night when he was doing his act two “Headlines” segment and put up a local newspaper’s Sunday TV listings insert. The cover featured a picture of Jay himself, with the tagline “Starring Jay Leno of ABC.”

  Jay, swallowed-canary grin firmly in place, peered into the camera and said: “Like a headline from the future.”

  On November 5, 2007, the monologues stopped—for everybody. Looking to press the networks and studios for a bigger payday from their material being used on new media like Internet videos and webisodes, writers walked off their jobs, shutting down every scripted show on television. That included the late-night shows, all of which relied on a stable of twelve to twenty writers.

  The late-night hosts felt the pressure almost immediately. They were all writers themselves, of course, and members of the Writers Guild of America. But they were also signature stars for their networks, and so usually much closer to the network management than stars of sitcoms in Hollywood were. The top network executives, sensing one way to undermine the solidarity of the union and its supporters among actors, directors, and the other Hollywood guilds, almost immediately pushed for the late-night hosts to return to work. They argued that the hosts could mount shows without the writers.

  The hosts had to add that pressure to the pain the strike was inflicting on their nonwriting staff members. Segment producers, researchers, assistants, and artists would all go without pay as the result of a game in which they had no stake. NBC told the producers of its two late-night shows that it would pay the staff through November, but after that layoffs would begin.

  O’Brien was the first host to pledge that he would pay the staff out of his own pocket, if it came to that. Jeff Ross made that promise public but tried to shame the network a bit by adding, “We’re hoping it will not be necessary because GE’s pockets are a lot deeper than Conan’s.”

  OʹBrien was not the only host taking steps to protect his staff. Jon Stewart had already given his group a similar assurance. David Letterman’s Worldwide Pants was already responsible for paying his staff directly, because in his unique arrangement with CBS, Letterman owned his show. The company announced that the staff of Letterman’s Late Show as well as that of The Late Late Show—which had installed Craig Ferguson as the new host less than a year earlier—would continue to be paid, but not in full. (Rob Burnett was already plotting a special course of action for Worldwide Pants.)

  Quietly several of the shows in New York began back-channel talks among themselves, hoping that there might be safety in numbers if they acted in concert in returning to the air. Letterman had to be looked to as the leader—he was the longest-serving host and obviously the prime mover in New York. All the shows wanted to return to the air, but they also wanted to respect the writers and their cause, and they also didn’t want to run afoul of any union stricture
s about what would be allowed on the air if they did return. (In essence, no written material, only ad libs, would be permitted.)

  Meanwhile, out west, Jay Leno was looking to do a little back-channeling of his own. While he made some gestures of support for the writers, including turning up on the picket lines with a stash of doughnuts, being off the air always drove Jay a little buggy. If there was going to be a way to get back on TV, Jay wanted to explore it. He reached out to a guy he suspected might be a kindred spirit, at least during the strike: ABC’s Jimmy Kimmel.

  That Jay could even have a civil discussion of any kind with Kimmel seemed beyond imagining only a short time earlier. Late-night competitors may have a history of barbed comments about each other; Kimmel’s early remarks about Jay were barbarous. A lifelong Letterman disciple, Jimmy had arrived in the late-night cauldron in 2003 spilling over with disdain for Leno and his brand of comedy.

  First Kimmel gave an interview in which he said of his upcoming ABC show, “I want to do the comedy version of The Tonight Show.ʺ Then, after Jay called Kimmel’s publicist to complain, Kimmel said he had only been goofing around, though he couldn’t help reacting publicly to the phone call by saying, “It’s just amazing how insecure he is.” Kimmel clearly had the prevailing view of most Letterman devotees: “Leno was so great when he was a guest on Letterman. Great, great. I just think he worked it too hard. I think he turned comedy into factory work—and it comes across.”

  Kimmel even rationalized about becoming a competitor to the great Dave himself by turning it against Leno. “I figure this: The people who like Leno are largely the stupid group. The people who root for Letterman are the smarter group. The people who like me? Also stupid. I figure I cut into the dummies.” And he suggested that his greatest fear in starting up his own talk show was the bad example the late-night audience was already setting. “In a world where Jay Leno beats David Letterman every night, you can’t be sure of anything.”