NBC didn’t even have a photograph of him that could be sent out with its press release, as Conan had never bothered to take a head shot—the principal calling card for any would-be performer. Every story wound up being illustrated with the same picture, lifted off the air: Conan with a goofy smile on his face towering over Leno on the
Tonight
stage. Conan found himself suspecting he was coming off like the Chauncey Gardiner character Peter Sellers played in the movie
Being There
. He pictured the CIA going though his suits in his LA apartment, ordering people to “pull the file on Conan O’Brien! There is no file? Pull the tape! There is no tape?”
NBC scheduled his press debut at the Rainbow Room in 30 Rock for a week later, on May 3. That day Conan proved he had some mettle. When he entered the building, he stepped into an elevator and was immediately confronted by a reporter from the
New York Post
, who taunted, “I counted how many laughs Letterman got in his press conference leaving the show and I’m gonna count how many you get!” Far from throwing Conan, the encounter relaxed him. It was when things were calm that he leaned toward depression or panic. When his back was against the wall, he seemed to do things he didn’t know he could do.
The press was charmed. Far from shrinking in the spotlight, Conan seemed to grow in it. He acknowledged being a “complete unknown.” He sparred with John Melendez, “Stuttering John” from Howard Stern’s radio show, exposing the silly disguise he was wearing. Conan seemed boyish, clever, fast with his wit, and fully appreciative of the absurdity of the position he was in. To buck him up, Lorne told him that day of an observation one of his fellow
SNL
writers, Bonnie Turner, had offered: “All I know is that guy will charm the shit out of any crowd.”
For Conan O’Brien nothing would ever quite match the thrill of that first time—his introduction to the American television audience on September 13, 1993. The first look anyone got of him was a pretaped cold opening—a segment run before the credits—in which young Conan strolled cheerfully through Manhattan, greeted by vendors, cabbies, and passers-by, all of whom had the same helpful message: “Lot of pressure—you better not screw this up.” When he arrived at the NBC building, he ran into the news anchor Tom Brokaw, who was sterner, and more specific: “You better be as good as Letterman—or else.”
Finally alone in his dressing room, showing no ill effects and whistling merrily, Conan pulled out a chair, stepped up on it, and in the same cheerful way swung a noose around his neck. In perhaps an inadvertent callback to the night of the Radcliffe Pitches, a stagehand knocked on the door to say it was time to go on. “Right now?” Conan asked meekly and then climbed down with a shrug, ready to step out onstage.
That introduction stamped him as an entertainer with obvious charm and pluck, and it was those qualities that dominated the early comments about the show. In
The New York Times
John O’Connor assessed the opening night as better than anyone could have expected, observing, “There’s a fine lunacy here that bears watching.” Others interpreted that lunacy as an indication that Conan was jumpy, tense, and ungainly. But in truth, he had not been overly anxious that first night. What looked like nerves was actually excitement. A charge had been lit under him; he was exploding with the thrill of knowing: Yes! This is it!
Of course it was near impossible not to start out rooting for a guy who seemed to have been pulled off the subway and handed a television show. Conan’s other early advantage was his relatively low profile in what had become a barroom brawl between the leading men in late night. Letterman stormed onto the air on CBS—as NBC suspected he would—and was already battering a reeling Leno. A bit later in September, Chevy Chase’s much anticipated new effort on Fox hit the air, but it was accompanied more by a thud than an explosion. A disaster that made for easy skeet-shooting for the critics, it helped keep the spotlight away from the new show on NBC.
Conan had the predictable growing pains—the learning curve was proving expectedly steep. But it occurred to him that even on the nights when the show seemed to be spinning out of his control—or else lying there like a beached tuna—something happened, one little moment, a witty remark or a shtick he tried with the camera—and the promise flashed through. To make Conan more comfortable they had installed one of the show’s new writers, Andy Richter, as a sidekick. It came about organically. The two of them had hit it off screwing around before the test shows. Jeff Ross saw that and guessed having somebody on set who Conan could “fuck around with” would help steady his jittery host. What they were all trying to do was different, even breakthrough, and some nights they did push it too far. “We were cocky,” Smigel said. “We really set out to do weird stuff. We just wanted to blow people away with how different the show was.” To Ross the whole show seemed to be “flying by the seat of our pants.”
In October, after only five weeks on the air, the Chevy Chase show was canceled. One of the writers broke the news to Conan, with a note of glee in his voice: They had already outlasted one of the big guys. Conan didn’t see it that way. “Oh, shit,” he said. “They’re going to reload.”
The mocking fusillade did begin soon after—not in a concentrated way, but more with a random shot here and there. The most persistent assault was coming from a high-profile voice. Tom Shales, the TV critic of
The Washington Post
, who had gained a reputation as the wittiest (if sometimes most purposefully astringent) assessor of the medium, with a special interest in the late-night arena, had already fired a few salvos toward Conan. He was one critic who had hated the opening night, having labeled Conan “a living collage of nervous habits—he giggles and titters, jiggles about and fiddles with his cuffs. He has dark, beady eyes like a rabbit.”
But five weeks later, Shales had poured a new store of powder into his cannon, and Conan was about to walk headfirst into the line of fire.
Looking to capitalize on the demise of Chevy Chase, NBC had set up a round of interviews for Conan, with Charlie Rose of PBS and a host of morning-drive radio DJs, which he would do from a studio in a single marathon session. Blissfully unaware of what had been printed that morning in Washington, he arrived for the round of publicity and discovered that every one of the questioners had seen Shales’s latest commentary about the show, and every one of them opted to read selections from it.
Such as: “Chevy Chase has done the honorable thing. Now Conan O’Brien should follow him off the cliff. . . . Let the host resume his previous identity: Conan O’Blivion. Hey you, Conan O’Brien! Get the heck off TV.”
The piece also managed to brand Andy Richter a “nitwit sidekick” and declared the show “as lifeless and messy as a road kill.” Shales suggested that Conan was “out of his head if he thinks the show is working” and had a firm recommendation for NBC: “Cancel O’Brien now.”
All Conan could do was pretend to find some humor in this drubbing, making as many self-deprecating jokes as possible. For hours worth of interviews the pummeling went on. When it was over, O’Brien walked outside in the rain to a waiting car. It was a weekday; he had a show to do. He slouched into 30 Rock, and in the
Late Night
offices the staff watched him slink past, afraid to say anything. O’Brien, the man who could fly high on comic inspiration, was also capable of the deepest of lows when he spiraled all the way down. He walked into his office, passed his assistant, and closed the inner door behind him. He made his way behind his desk, stood there for a second, then bent, went to his knees, and crawled down under it.
He rolled on his back and just lay there until after a while he heard the door creak open a crack. The door closed, and a few minutes later—Conan still hadn’t moved—it opened again. He recognized the shoes: Ross.
“Are you OK?” Jeff asked, masking the concern with a little touch of playful rue.
“I’m gonna be fine,” the voice from under the desk said. “I just need to be under here for a little bit and just lie here.”
For the most part, all of them—Michaels, Polone, Ross—tried to shield Conan. Not from the press; that was impossible. What they worried about was his getting wind of the building dissatisfaction at the network. The numbers weren’t very good—not awful yet, but clearly a concern. Worse was the network’s assessment of the show. The executives wasted few chances in ripping it in private conversations; Conan was getting no better. The comedy was more weird than funny. He didn’t listen to the guests in the interviews. And Andy . . . He was like an affront to the concept of entertainment. Polone got a call from Warren Littlefield excoriating the show and Conan. “And get that fat, fucking dildo off the couch!” he demanded. Most everybody on the show loved Andy; so, apparently, did the studio audiences. But Polone had little ammunition to fire back. The ratings showed no growth, and the critics were annihilating Conan.
For that, OʹBrien could not fully blame them. He could feel the show coming together in little ways, but he knew it wasn’t there yet—or even close. How could he blame anyone, viewers or critics, who had been accustomed to seeing someone like Letterman at that hour? It struck him that the comparison might be one his dad would have made about the great Red Sox star of his generation: “Ted Williams has departed the field. But here to replace him, ladies and gentlemen, number seventeen and a half, Chip Whitley!” Conan pictured a kid running out onto the field in a diaper and saying in a high-pitched voice: “Hi, everybody! Gee, I’m gonna miss Mr. Williams too, but don’t you worry!” And then the kid would pop out.
The flaws were everywhere. The comedy might miss, and then the distraction would spill over into the guest interviews. About four months in, his old Chicago pal Jeff Garlin called with some advice. “I don’t know what anybody is telling you. You’re doing a great job. You’re funny. But in the interviews you’re just not listening to a word anybody says. You really need to get into listening.”
It was midway through the first year that Ross heard the serious rumblings begin. Affiliates were unhappy; what if they started to preempt? NBC had already hired a young hotshot named Greg Kinnear to succeed Costas as host of
Later
. Word was filtering out about how much the network loved the guy—and why the hell hadn’t they given
him
the 12:35 show in the first place?
In the spring of 1994 Conan was due for a twenty-six-week pickup—Conan had a one-year deal but the show had an original commitment of only twenty-six weeks. Polone dutifully called John Agoglia, the deal guy for NBC, who told him they were picking up Conan for the next six months. Polone said that was great, but the contract required he get the extension in writing.
“I can’t give it to you in writing right now,” Agoglia told him. “We’re having some affiliate problems. But don’t worry about it; you’re picked up.” He said he merely needed another month before committing the deal to writing.
“Well, if we’re picked up, what’s the difference?” Polone said. “You’re just giving me a piece of paper. I’m not sending it to
The New York Times
.”
Agoglia hedged again, assuring Polone that he needn’t worry about it. But Polone did, becoming suspicious that everything with NBC was not what it seemed. The Kinnear talk only made him more uncomfortable, but he had no juice to use against the network. They would simply have to wait for the paperwork.
As spring turned to early summer, Conan remained on the air, but without a document that made his renewal official. Polone went off to Cancun on vacation, but on Friday of his week away he decided to call in to NBC; the time on the extension was up, and all was still quiet at the network.
“Yeah, we got a problem,” Agoglia finally admitted to Polone. “We’re going to be picking him up week to week.”
“Week to week!” Polone exploded. “You told me we were picked up for the twenty-six weeks. You lied to me!”
Agoglia, all business, never thrown by high emotion, shrugged that off. “What are you gonna do?”
Polone called in to New York and broke the news to Ross, who didn’t share it with Conan until after the show that night, honoring a fundamental rule of good show business: Don’t rattle your star before a performance. None of them could believe NBC was pulling this. Week-to-week renewals? No one had ever heard of such a thing. O’Brien, Ross, and Smigel met in Ross’s office after the show and put the speakerphone on the floor. The three of them—partly to hear better, partly just worn down from another week of shows and more disrespect from NBC—sprawled themselves on the rug surrounding the phone as they put in a call to Cancun.
Ross argued that Polone had to make a counter to NBC right away. “If they aren’t going to give us the six-month pickup, we can’t give them week to week. The blood’s in the water then. Everyone will take it that we’re being canceled.” How many people—writers, segment producers, publicists for the guests, anyone—would stick with a show that was on a weekly deathwatch? “We gotta get them to go up to thirteen-week renewals,” Ross insisted.
That was the plea that Gavin made to Don Ohlmeyer, appealing to Don’s sense of fairness. Polone had always been impressed that Ohlmeyer, who started in the business as a sports producer (most famously of
Monday Night Football
in its heyday), was not a typical network executive. “In the entertainment industry,” as Polone assessed it, “you very rarely sit down with someone and have a bacon cheeseburger and then light up a smoke afterward. You’re on a different planet when that happens.”
Ohlmeyer listened to Polone’s plea and granted a reprieve. NBC would extend Conan in thirteen-week increments. At the same time, he set some ratings targets Conan would have to reach. Instead of a vote of no confidence, they now had a vote of minuscule confidence.
To Ross, NBC’s moves felt cheesy—and personally shitty. Conan was making so little by late-night host standards—only about $1 million—that it would have been a minimal risk to NBC to extend him the full six months and pay him off if he didn’t cut it. To make them grovel like this had an edge of purposeful nastiness to it.