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Cover Story: Time to Produce at 11:35

Jeff Ross is newly installed as executive producer of The Tonight Show, beginning June 1, and already industry followers are talking about the presumed booking war between his guy, Conan O'Brien, and Jay Leno's new 10 p.m. show.

“I'm in touch with [Leno's producer] Debbie Vickers, and we talk all the time and we'll just figure it out,” Ross says. Then, with the dry wit that has helped guide O'Brien to the huge 11:35 promotion, he adds, “It won't be a war; maybe just a skirmish.”

Joking aside, Ross understands the magnitude of what he is about to take on. While he is anxious, supplanting a late-night giant is nothing new to him or his host. It was O'Brien who, in 1993, began hosting Late Night, stepping in for David Letterman after he'd famously jumped to CBS.

“Of course I am nervous,” Ross acknowledges. “It's daunting. But there seems to be a lot less pressure than there was for us in 1993. Nobody ever replaced Letterman when he was the hottest thing in show business.”

But replacing Jay Leno on one of network television's most storied franchises will train plenty of spotlight on O'Brien. And behind the scenes, as he has done for 16 years, it will be up to Ross to make sure everything goes smoothly.

“Conan's been a huge success, but I think Jeff has made him even better,” says NBC Universal chief Jeff Zucker. “He may be the coolest and clearest-thinking exec in show business.”

Born on Manhattan's Upper West Side, Ross attended NYU, where he booked incoming concerts. From there, he went on the road with musical acts including AC/DC and Diana Ross (no relation).

When given the chance to transition into TV production, he jumped, working on both musical and comedy specials. Things changed considerably when he met Lorne Michaels on the same Universal lot on which he will be producing The Tonight Show. It was there Michaels asked him to start a show based on the Canadian sketch series, The Kids in the Hall.

A New Guy Gets the Desk Job

Then in 1993, Michaels asked Ross to produce Late Night, even before they knew who the talent replacing Letterman was going to be. Soon after, Michaels introduced Ross to a virtual unknown named Conan O'Brien. Michaels wanted to test him on the set of The Tonight Show to see if he could do the job.

The two set up a meeting at The Four Seasons Hotel in Beverly Hills, where Ross was staying. O'Brien walked the few blocks from his nearby apartment and called up to Ross' room.

When Ross came down to the lounge, O'Brien was sitting at a chair behind a table with a couch pushed next to it, the arrangement of a talk show set. O'Brien looked up at Ross and said, “What do you think, this looks good, huh?” Their versions of Ross' reaction vary. Ross says he remembers thinking O'Brien looked good there. O'Brien says Ross just “made a face like, 'You're kidding, right?'”

But O'Brien believes he won Ross over at the audition—judging by one brief encounter. During a break, Ross walked up to a “disheveled” O'Brien, as the host describes himself on that day, when he was sporting a brand new suit jacket (he hadn't owned one before, so Lisa Kudrow helped him pick one out that day). Ross approached O'Brien, straightened his tie and said, “You're doing pretty good.” Not exactly effusive praise from many, but O'Brien could tell that the low-key Ross was starting to think this could just work.

But the decision wasn't his, and Ross was realistic: If a bigger name were chosen—and plenty were rumored—he might not get to produce. If Conan got the gig, however, Ross knew he was in.

Three weeks later, after the Late Night host decision had been made, Ross came back from a lunch to more than 20 messages from people like O'Brien, Michaels and several NBC executives. “We thought Garry Shandling was going to get it,” Ross remembers. “When I got back from lunch, it was obvious that didn't happen.”

Sixteen years later, O'Brien is now a household name, but that was hardly the case at the beginning. “We always knew we could get canceled at any time,” Ross recalls. “I honestly think we were a few times and then got lucky. There were a few regime changes. Plus, I don't think anyone at the network other than [late-night chief] Rick Ludwin actually watched the show and he just said, 'Leave them alone and they'll figure it out.' That was the beauty of being on at 12:30.”

But Ross and O'Brien built a unique franchise of their own—from masturbating bears to a famous show from Finland. And they also built a very complementary relationship.

“Jeff and I are completely different rhythms,” O'Brien says. “I'm high-strung and moody, and my highs are really high and my lows really low. Like I said on-air my last night, he cheers me up when I'm down and depresses me when I'm up.”

O'Brien also likes that Ross is not afraid to give him dissenting opinions. “When I started, Garry Shandling asked me if I have too many yes-men,” O'Brien remembers. “Sometimes I would kill for a yes-man. Jeff is completely honest with me. We argue, but Jeff doesn't trade in compliments, doesn't waste time stroking my ego.”

And with Ross behind him, O'Brien had built up enough power that NBC, when faced with losing him, made the unprecedented decision in 2004 to announce O'Brien as eventual Tonight Show host—five years before he would take over. After watching all the fireworks around the 1993 shakeup that saw Leno get the big chair and Letterman bail to CBS, Ross suddenly was living it. O'Brien had other suitors, but NBC wanted him to trust that they would deliver The Tonight Show in 2009.

“It all happened so fast, and was so surreal when it was happening,” Ross says. “When someone comes and says, 'Do you want The Tonight Show or do you want a lot of money to go somewhere else?' it's fun. Stress-inducing, but fun.”

And O'Brien says Ross was a huge part of the decision. “He didn't push me in one direction or anything, but all the conversations were pretty much Jeff and myself,” O'Brien says. “We do have similarities, and we both had the same feeling about The Tonight Show and what it meant.”

Ludwin also could tell how important Ross was in the decision-making process. “I wasn't privy to all their conversations, of course, but they seemed very concerned with whether the offer was real and we were going to go forward with it,” he says. “We just assured them it wasn't going to be a bait-and-switch, and it seemed like Jeff was very influential in the decision.”

More Than Money

Even after the announcement that O'Brien would stay with NBC, there were doubts around the industry. NBC could have written O'Brien a fat check (said to be around $45 million) and kept Leno at 11:35.

“I had heads of networks say to me, 'You realize [The Tonight Show] will never happen, you're going to get paid off,'” Ross says. “But I never believed it, truly.”

And then NBC shocked the TV world by getting Leno to stay and host a nightly show at 10 p.m. O'Brien and Ross found out when Zucker and Ludwin came to tell them last December in the producer's office. The executives broke the news, and Ludwin remembers watching O'Brien and Ross take it all in. And then Ross spoke up and was the first to say to O'Brien that it was going to be good for them.

“We always knew they were trying to make a deal with Leno to stay, but it was a little bit of a surprise it was every night at 10,” Ross acknowledges. “At the end of the day, it was have him on at 10, or have him up against us at ABC.”

Now Ross is ready to get back on the air. Really ready. He hasn't done a show since O'Brien handed the Late Night reigns to Jimmy Fallon on Feb. 20, the longest he's gone without doing a show in 16 years. “Enough meetings, let's do a show already,” he says.

But this week, it's not any show. It's The Tonight Show.