The War for Late Night Read online

  What separated them—really what separated Colbert from almost everyone else in his youth—was a tragedy. When he was ten, his father and the two brothers closest to him in age (he had eleven siblings in all) were killed in a plane crash on their way to enroll the boys in a boarding school. Colbert could never fully calculate the devastation that the loss wrought, on his family or his own young psyche.

  Stephen all but shut down academically, turning instead to fantasy books, which he escaped into by devouring them at breakneck pace. “Nothing seemed important after that,” Colbert said of the tragedy, a feeling that sparked a lifelong resistance to “blind acceptance of authority.” He felt detached from the standard interests and behavior of children. Nothing a teacher could say could inspire any discipline, because after what had happened to his family “nothing seemed threatening to me.” He did try to make his mother laugh, as humor was respected, even valued in the family. But the young Colbert wanted to be less ham than Hamlet, “so I could share my misery with the world.”

  He started at Hampden-Sydney College in Virginia, where he finally got a little serious about using his intellect—when he wasn’t consumed by playing Dungeons and Dragons, which he later credited with fueling his character-creation skills. After two years he transferred to Northwestern to chase his serious acting muse.

  On his flight to Chicago to enroll, he fell into conversation with a fellow passenger—an unnamed astronaut, in Colbert’s telling—and described how his dad at one time considered shifting the second syllable of their name to the French pronunciation, but didn’t out of deference to his own father, “who lacked the pretentious gene I have.” Advised by his seatmate to go for it if he really wanted to change his life, COLE-burt landed in Chicago as Cole-BEAR.

  Acting at Northwestern, he discovered that he appreciated comic roles—and being around the funnier people—more than that grim, tragic stuff. After trying other groups in Chicago, Colbert eventually signed on to the famous Second City improv troupe and truly found his form. He met some significant future contacts there, including Steve Carell (Colbert became his understudy) and Amy Sedaris. With Amy and Paul Dinello, Colbert went on to create a sketch comedy show for Comedy Central in 1995, Exit 57. (Later the threesome would also launch the surreal series Strangers with Candy for the channel, which gained a cult following, mainly for Sedaris.)

  Though Colbert had not quite broken through, he was finding a consistent theme for his characters: totally sure of themselves and completely ignorant, or as he put it, “poorly informed, high-status idiots.” Something about that combination sounded like a perfect profile for television news correspondent, or at least ABC’s Good Morning America thought so. In one of network news’s periodic attempts to try something different—or funny—GMA hired Colbert as a comedy correspondent to play off the serious anchorman Charlie Gibson.

  Colbert certainly looked the part. He had a bookish demeanor behind his spectacles, wore a suit well, like a professional something, and kept his dark hair shortish and precisely in place. Of average height, weight, and appearance, Stephen could have found a niche in the fifties playing Jim Anderson’s best friend from the insurance office on Father Knows Best. Except he was really funny—and, yes, kind of subversive. (That didn’t describe his personal life, which really did seem right out of Father Knows Best. Colbert, happily married to Evelyn McGee, also a South Carolinian, was the father of three and lived in suburban conventionality in Montclair, New Jersey, where he also taught Sunday school in his local Catholic parish.)

  Ultimately Colbert was apparently too funny—or subversive—for Good Morning America, which didn’t dare try many of his ideas on their show. (Two of about twenty he proposed were filmed; only one aired.) But the experience did leave him with a real press credential, which helped land him a tryout on the just emerging Daily Show in 1997, when Craig Kilborn was still the host. The faux, full-of-it correspondent turned out to be the ideal expression of the Colbert character, but he hit his full stride only when Jon Stewart took over the show in 1999 and raised the show’s comedy threat level from broad to biting. Colbert’s smug, know-nothing know-it-all began to take shape, and after the show’s first star correspondent, Colbert’s former Second City mate Steve Carell, left for movie fame, Stephen became the breakout feature player for the show’s growing legion of fans.

  Colbert’s pompous conservative egotist eventually took over for the merely moronic correspondent. Comedy Central had been looking for a companion series to run at eleven thirty following The Daily Show. Stewart had by this time become more or less Colbert’s professional brother (among other things, they also shared an agent, the ultra-ubiquitous James Dixon), and Jon’s Busboy Productions became the producing entity for the new show. Success came instantly; Comedy Central commissioned a study in 2008 showing that the degree of passion and loyalty expressed toward Stewart and Colbert dwarfed anything else in late-night television. For a time Colbert faced some questions about whether he could possibly sustain a talk show essentially acting every night instead of presenting himself and his own views. Five years in, he answered those questions nightly, modifying his character slowly and subtly over time to add dimension to the show—and to the host’s future possibilities.

  Some of those close to Stewart and Colbert suggested that Jon was now well settled and needed nothing more from his career than continuing what had become, professionally and culturally, the job of a lifetime. But Stephen Colbert? He might be up for much bigger ambitions, colleagues said—like reinventing what it was the networks were doing with their late-night shows. If they ever decided to break the form—the couch, the desk, the band, the jokey monologue—Colbert had by 2009 earned a spot high on the candidate list; he had certainly proved he had the creative nerviness to do it.

  A few weeks into Conan’s run, a single dark-shaded cloud began to drift across the Manhattan sky, sinking just low enough to pose a threat of interfering, ever so slightly, with the spectacular views outside the CEOʹs office on the fifty-second floor of 30 Rock. Jeff Zucker was starting to feel less than thrilled with the way The Tonight Show was going, an opinion he had already expressed to NBC’s late-night executives on the West Coast, Rick Ludwin and Nick Bernstein.

  There were two issues, as Zucker saw it. One was Conan’s performance. By his reckoning, Conan looked tentative, not relaxed enough. That could be expected and tolerated, to a point. People get a case of nerves starting a huge career move like this.

  But as far as Zucker was concerned, there was less excuse for the second issue: missteps in guest bookings. Zucker, of course, had a great deal of accrued experience from running Today, where bookings were the lifeblood of the program (and the ratings). While each show had its own booking staff that made most of the calls, landing the biggest names often required the intervention of a star like a Katie Couric (or a star producer, like Jeff Zucker). Even close to ten years past his Today tenure, if there was one thing Zucker knew as well as or better than anybody else in the business, it was how to book for numbers. And he thought Conan and his team weren’t doing it.

  To what extent that was purely Zucker’s view as opposed to how much he was being influenced by what was being murmured in his ear wasn’t totally clear to those on whom Jeff unloaded this opinion. Others at NBC were already aware that Dick Ebersol, the man whose judgment Zucker was most apt to rely on and trust, had tipped over entirely to the negative side about Conan. Ebersol’s reservations—and unhappiness at how Conan had reacted to his voluntary consultant role—had hardened, within days of the premiere.

  As the shows piled up, Ebersol’s critique grew only more pointed. The focus group tape late in the first week was funny, but it almost seemed designed to offend older viewers—however many were left by that point. The music performances in the last act of the show seemed calculated to encourage the nonhip to hit the road. Even Pearl Jam, which seemed like a booking coup on Conan’s first night, had irritated Ebersol. He knew the group had many great songs, but
what they played (“Get Some”) seemed to Dick—admittedly, at sixty-two, not the precise target audience for that brand of rock—to push past entertainment and toward a test of how much hearing loss a human could comfortably suffer. Alienating music acts were not going to help drive Tonight audiences into Jimmy Fallon either, Ebersol, who was already most impressed with Fallon’s early efforts, concluded.

  Dick’s concerns actually started at the very top of the show—with Andy. Conan had managed just fine, it seemed to Dick, after Richter left the Late Night show in 2000. That Conan had decided to bring him back when he was starting up Tonight boggled Ebersol’s mind. He could not conceive of a thing Andy brought to the show, other than serving as a baby blanket for Conan. The interaction between Conan and Andy made Ebersol wince. During the monologue Conan would hit a joke, and Andy—off camera, to Conan’s right, audibly mic’d—would occasionally respond with a comeback, almost every one of which cracked Conan up. (Indeed, one star of another late-night show was in awe of Richter because “he scored every time he opened his mouth.”)

  Andy didn’t crack up Ebersol. Worse, Dick thought the nightly remarks from Andy, which Conan would then respond to, had the effect of a bouncer shooing would-be attendees away. Their exchanges played to Dick like two guys having a conversation the audience wasn’t a part of, with Conan glancing off camera for a significant portion of his monologue, checking Andy’s reaction. Every second he was doing that, he wasn’t talking directly to the people lying in their beds with the TV on.

  But more than anything else, what had raised Ebersol’s finely attuned late-night hackles was precisely what had alarmed Zucker: the booking issue. Here was Conan, assuming control of the biggest platform in show business, and in his second week—on only his ninth Tonight Show—his lead guest was, incredibly, Norm MacDonald. The onetime SNL player had not, as far as Ebersol knew, had a prominent show-business job in years. Ebersol thought the show might as well have booked Norm Crosby.

  Of course, for Conan’s true fans, the MacDonald booking was cause for real excitement. He had always been one of O’Brien’s signature guests, and he always seemed to delight Conan. (And that night, he killed Conan again, at one point driving the host to stand up and flee the desk after some banter with Andy.) To not appreciate Norm, and what he brought every time he visited, was to not be a Conan fan at all.

  Again, to Ebersol, that attitude seemed a signal that Conan had circled the wagons and was including within the circle only those who shared the faith and had signed a religious pact to travel west with him. That did not include Jay’s fans, of course, who were effectively being disinvited. When Kevin Nealon, another long-absent SNL vet, turned up on the couch the next night, Ebersol was simply dumbfounded.

  In general, Ludwin did not disagree with these concerns. But he always approached his role in trying to manage Conan and his team from a point of unfettered admiration for the comic’s talent. He believed Conan was brilliant, pure and simple; he saw Conan as the future. Still, even in the Late Night days, Ludwin himself had felt the need to prod the staff in terms of bookings. It seemed to Rick that Conan’s booking department still had a 12:35 mentality, that they sought out what he saw as the more quirky, less mainstream kind of showbiz guest. He wasn’t sure they understood, or simply didn’t embrace, the arm-twisting clout that The Tonight Show could wield over top guests.

  In theory Ludwin had no issue with someone like Norm MacDonald as a lead guest. He knew how funny Norm had been with Conan on many occasions, and every host had those guests who simply played so well with them that they made for attractive and frequent bookings. For years Letterman had booked Charles Grodin because of the killer shtick the two of them had developed, not because Grodin was a big star. Rick’s own reservation was about the approach Norm sometimes took to his visitations with Conan, when he would come on and simply tell old jokes, rather than extending himself a bit and being more topical, which might lure in a larger audience.

  The disconnect over booking policy did not spring from arrogance, Ludwin was sure. Conan and his staff wanted the show to be organic, he believed, always consistent within Conan’s sensibility. Nothing should look as though he was merely taking network notes, because then the fans really might believe he was selling out. And Ludwin never underestimated the effects of the heat from the cauldron Conan had stepped into. The Tonight Show remained the pinnacle of show business for the NBC late-night executive. As he saw it, only five men could ever really know what it was like to assume the mantle of hosting that institution—and how much pressure that inflicted. So he continued to nudge Conan and Jeff Ross gently toward broader, more 11:35-style guests, toward finding ways to “make the show bigger.”

  Lorne Michaels, meanwhile, was watching the show and having a different reaction: In some ways it looked too big. The move to a soundstage had undoubtedly opened up the show, but maybe not all to the good. In New York, with its tight quarters, set builders and directors did everything they could to make studios look larger, the same way New Yorkers try to use space wisely to make their apartments look more spacious. In LA, the soundstage space was so wide open, the show did not look intimate anyway. Michaels knew the center of the show was always going to be Conan O’Brien, not some sprawling set that some viewers might suspect came from a page in Architectural Digest.

  Once, when filming a scene from a movie in an Indian casino in the Southwest, Michaels and his cast and crew had been struck by how grim and tawdry the setting seemed, with old women betting quarters and six-hundred-pound people playing slots. But in that room at night, on every TV monitor, Lorne noticed that Leno was playing—and that seemed right. “Oh, this is America,” Michaels concluded. Picturing Conan on those monitors threw the imagery off somehow, for Michaels. Something about it sent a message that this old familiar show had gone upmarket.

  Knowing and recognizing television was like knowing and recognizing candy bars, Michaels reasoned. You anticipated what you would get for your dime or quarter or dollar (depending on how old you were). Snickers? That was the one with nuts. If somehow that relationship changed, because the wrapper made it odder or more expensive looking, you might get confused and think maybe that wasn’t the candy bar you wanted after all. It might still be a good one, of course, but it wasn’t the one you knew. If it had the look of having gone upmarket, maybe you’d look around for a different candy bar.

  The accumulated wisdom of all this analysis reached the Conan team in drips and splashes. Jeff Ross was having lunch a lot at the Grill on the Universal lot with Marc Graboff and listening to what Marc was hearing from New York—nothing really different from what was in the notes Ludwin and Bernstein were delivering in LA. Graboff didn’t think Jeff had slipped on a pair of rose-colored glasses; he always seemed to appreciate the inside intelligence.

  But the heavy-rotation concentration on the bookings drove Ross a little mad. Of course they were trying to book the best names they could; they weren’t idiots. They always sought the A-list. But it was early summer, and how many A-list stars were making the rounds unless they were in summer popcorn movies, which were usually about robots anyway?

  The music complaints seemed even sillier to Ross. The notes said, put on more music with wide appeal. Like who? Ross asked. There were only so many American Idol losers available. He checked his list: The music acts seemed to have a high quotient of crossover artists, with many singers Leno had previously booked.

  One note from the network did get addressed quickly. As early as the first night no one had liked the way Andy did the voice-over opening. To many inside NBC it sounded like Richter was putting a little ironic top-spin in his inflection of “Conan OʹBriiii-en,” with the last syllable trailing off like the fade-out at the end of a song—as though Andy was partly spoofing the role of the announcer. That element got fixed

  One other element—and a significant one, as far as Jeff Zucker was concerned—did not.

  Jeff Zucker had never completely hung up his Today show
cleats—the ones he had used, with recurring glee, to stomp on competitors when he produced the show in the nineties. Even as CEO of the far-flung NBC Universal entertainment empire (cable channels, broadcast network, movie studio, theme parks), he was still known to check in on occasion with the Today producer Jim Bell to suggest a segment—or, more frequently, a booking. Zucker prided himself on knowing a great story when he saw one, and the best way for a television show to take advantage of that story.

  So as June rolled by with the press taking note of Conan’s shrinking margins over Letterman—and by week three Dave had edged past Conan in viewers for a full week (though Conan continued to crush Dave in the young demos)—Zucker saw the kind of wide-open opportunity that used to ring his wake-up alarm in the mornings:

  Sarah Palin.

  Always a magnet for press attention, Palin had jumped on an insult to her young daughter to launch a summer publicity offensive. And the target of her righteous parental wrath was none other than David Letterman, who had stumbled into Palin’s PR gunsights by cracking a joke that would have wandered dangerously close to offensive even if it had been accurate. The fact that it wasn’t only set Letterman up as easy prey for the former governor of Alaska.

  On June 9, with Conan just starting his second week on his show, Dave told a joke about Palin’s visiting Yankee Stadium with her daughter. “One awkward moment for Sarah Palin,” Letterman said. “During the seventh-inning stretch her daughter was knocked up by Alex Rodriguez.”

  Everyone knew Palin’s unmarried eighteen-year-old daughter, Bristol, had gotten pregnant by her boyfriend and now had a child. Bristol wasn’t the daughter who accompanied Palin to the stadium, however. It was Palin’s fourteen-year-old, Willow.