The War for Late Night (34 page)

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.