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THR Cover: Conan O'Brien: End of the Pity Party

This story first appeared in the June 1 issue of The Hollywood Reporter magazine.

Conan O'Brien sits inside Prosecco, a trattoria in L.A.'s Toluca Lake, sipping Pinot Noir on the night of April 17 and ponders the reality that his 49th birthday is just hours away.

"Tall people getting older is funny because they often don't," says the 6-foot-4 O'Brien, postshow in a striped V-neck sweater and black slacks, his leather jacket draped over a chair. "I'm like those junk trees that grow really tall, really fast, then fall to pieces. I'll be doing a monologue five years from now, and there will be an audible crackling sound."

As if on cue, a waiter appears with a birthday candle-embellished dessert of panna cotta.

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"How lovely and embarrassing!" says O'Brien.

"Do you want us to sing to you?" asks a stylish fiftysomething woman at the next table with her husband and another couple.

During the next few minutes, O'Brien chats with the couples about schools, bar mitzvahs, his two young children, the work he and his wife, Liza, have done with the Children's Defense Fund.

This reporter interrupts to point out that the wax on his birthday candle is melting away.

"OK. … I wish a good year for all of us!" says O'Brien, blowing out the candle. "By the way," he adds: "I lied about caring about the underprivileged because there's a reporter here. I'm looking out for No. 1. Me and Mitt Romney."

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After the diners leave, he says: "That was nice. I like talking to people. It's tough to be in this business if you don't enjoy those moments."

♦♦♦♦♦

Back in January 2010, there weren't many moments to savor following his spectacularly acrimonious exit from NBC -- one that netted O'Brien a reported $30 million buyout but cost him his dream job as host of The Tonight Show. On May 17, when he and fellow NBC exile David Letterman sat down together on Late Show -- O'Brien's first guest spot on the CBS show in 13 years -- things seemed to have come full circle as the two discussed the worst 10 days of O'Brien's career or, as Letterman put it about the NBC debacle, "some kind of mix-up." With Letterman baiting, they playfully bashed Tonight's Jay Leno in a way that wouldn't have been nearly as funny only a year ago. At that point, total viewership for the first season of O'Brien's TBS late-night show, Conan, had dropped from a high of 4.2 million the first night of its November 2010 debut to a monthly low of 876,000 -- behind Comedy Central's The Daily Show With Jon Stewart and The Colbert Report and even, on some nights, E!'s Chelsea Lately. Ratings expectations were great when Conan debuted; when the numbers tanked, TBS had to offer advertisers "make goods."

"TBS' pricey Conan O'Brien experiment is flopping," chided the Wall Street Journal in August. Even worse, others were buzzing that he'd given in to self-pity and lost his comic edge. The 2011 documentary Conan O'Brien Can't Stop, about his post-Tonight Legally Prohibited From Being Funny on Television Tour and a 2010 60 Minutes appearance did him no favors with some observers who complained that he'd become "whiny." Vanity Fair's James Wolcott said O'Brien "came off as a peevish straw of nervous energy … a self-involved chatterbox."

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Sitting with Letterman, though, O'Brien looked relaxed and happy. And why not? One day earlier, he had brought down the house at Turner Entertainment's ambitious upfront rollout in New York's Hammerstein Ballroom throwing barbs at execs via Conan's popular fake Craigslist ads. For Les Moonves: "HOUSE SWAP: "My $20 million house in Brentwood for my $30 million house in Malibu. Ha, just kidding! They're both my houses! God, I'm rich!" More significant, TBS announced at the upfront that the Tosh.0-esque Deon Cole's Black Box from O'Brien's Conaco production company would air in 2013; this is on top of a handful of other scripted comedies in various stages of production and development, including a soon-to-be-announced late-night show for the midnight slot following Conan. "Conan is our Mount Rushmore," says Turner chief Steve Koonin, who in February re-upped O'Brien's initial reported $12 million contract through 2014. "We've made him the centerpiece of TBS. If success were only about ratings, we'd just run Westerns all the time. We're never going to be Leno and Letterman, and that's great. To be second to Stewart and Colbert is OK with us."

Yes, Conan's ratings still lag those of Comedy Central's basic cable power duo, but during the past six months, O'Brien's audience has grown to 1.1 million viewers (Letterman and Leno have 3.4 and 3.8 million, respectively). TBS also has carved data from the 18-to-49 demographic to show Conan outperforms every network late-night show in the 18-to-34 demo and has the youngest average viewer age: 35 (57 percent of that audience is male).

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Beyond ratings, O'Brien is exploiting new viewing platforms and invading the digital space with a vigor that has made him a new type of television pioneer. He has the most Twitter followers of any late-night host (5,673,313); more Facebook fans (1,862,368) than Jimmy Kimmel, Leno, Jimmy Fallon, Letterman and Craig Ferguson; and TeamCoco.com streamed more than 12 million videos in March, up 22 percent from 2011. His AT&T-sponsored Conan-synchronized tablet app allows viewers to experience video clips and other bonus content in real time and has streamed 1 million episodes since its February launch.

This is why, instead of backing down when ratings sank, TBS went all in and invested a reported $1.5 million an episode to air The Big Bang Theory reruns as a youth-targeted lead-in for Conan. The cable network best known for Tyler Perry sitcoms is betting its future on the still-youthful-by-late-night-standards O'Brien and hoping to attract his younger, digital-savvy audience and rebrand the network, which has struggled to make a splash with original comedy.

"Here's what Conan is doing that's very smart -- advertisers don't only want large numbers for specific demos; they want an engaged audience," says Larry Chiagouris, marketing professor at Pace University's Lubin School of Business and former chair of the Advertising Research Foundation. "The more you engage with your audience, the more you develop a relationship with them, they tune in and pay attention to the commercial messages. The average Conan viewer is more engaged with his program than the average viewer of Jay Leno's. I would bet on it."

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Certainly, TBS' pro-digital, post-ratings approach is yielding innovative ad dollars from large advertisers like AT&T, which sponsors the Conan sync app. "There are more important things to determine the efficacy of an ad campaign than the ratings of people tuning in on a certain night," says Chet Fenster, managing partner at MEC Entertainment, a division of the global media agency that helped craft AT&T's partnership with Turner. "Advertisers want to be where the consumer is … Facebook, Twitter. The key demo is 18-to-34 -- that's the sweet spot."

It's also an audience that can help create buzz. On the afternoon of March 28, Paramount gave Will Ferrell the go-ahead for the much-anticipated sequel to 2004's Anchorman: The Legend of Ron Burgundy, and the comedian needed to make a fast decision about how to announce the movie. "We had 24 hours to do something before the news leaked," says Ferrell. "Conan was our first call."

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By 4:45 p.m., the actor, in full Burgundian polyblend splendor, made an entrance before O'Brien's audience and proclaimed "to everyone here in the Americas, to our friends in Spain, Turkey and the U.K. -- including England" that there would be an Anchorman sequel.

The bit resonated not only within the studio and for viewers but also generated 3 million Internet views within 24 hours on 700 unique sites. "Conan's show had the perfect vibe for that kind of announcement," says Ferrell. "We were really happy for him to reap the benefits."

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Says O'Brien: "What we are trying to do is a mosaic; you can't really see the whole picture until you back up. At NBC, we were a small comedy club on a cruise ship. At TBS, we're masters of our own pirate ship. It's about so much more than who watches the show at 11 p.m. Who watches it at 1 a.m.? Who watches the clip online the next day? Who sees the ad with that clip? This is where it's all going, so let's get ahead of it rather than pretend it's still about America gathering around the TV to watch Roots or Ed Sullivan. That simply isn't the case anymore."

♦♦♦♦♦

It's a late-April afternoon, and O'Brien is in deep in rehearsal mode on Warner Bros.' Stage 14 in Burbank -- the same place where classic movies such as Casablanca and Ghostbusters filmed and only 2,112 feet from the set where Leno is preparing for The Tonight Show.

A dozen college interns, the show's de facto focus group, watch as O'Brien, relaxed in a striped navy hoodie and jeans, plays riffs from The White Stripes' "Seven Nation Army" on an electric guitar. Squeezed together on the small guest couch are O'Brien's longtime producer Jeff Ross, always in a suit jacket, the most businesslike and soft-spoken of the group; head writer Mike Sweeney, a white-haired but still youthful-looking former attorney whose jeans-and-sneakers affect is less lawyer-producer than high school math teacher; producer Tracy King, a self-described geek and gamer who started on Late Night; and original sidekick Andy Richter, not yet dressed for airtime in a white T-shirt and jeans. While they review notes for tonight's show -- with guests Kathy Griffin and Super Size Me director Morgan Spurlock (the all-redhead lineup purely a coincidence) -- O'Brien tests a bluesy guitar sequence for Jimmy Vivino, the goateed leader of the show's Basic Cable Band.

At 2 p.m., still strapped with his ax, the host settles at his large wooden desk to run through the introduction to Conan's regular Monday segment "Fan Correktions," wherein nerdy YouTubers try, but always fail, to catch O'Brien in an error from an earlier episode.

Tonight, O'Brien is responding to an Ithaca college student who points out that the upcoming Batman sequel is The Dark Knight Rises -- not Rising. "Sorry," says O'Brien, from his desk. "I was actually referencing The Dark Knight Rising, the adult film based on The Dark Knight Rises." The lights dim, and a video clip appears on the monitors featuring three costumed Conan writers mimicking a superhero three-way. The bit -- a perfect example of the type of comedy that alienated Tonight's older, mainstream audience -- kills. The interns explode with laughter, and O'Brien, quite serious until now, chuckles.

"After our first TBS meeting, when the Fox deal was falling apart [O'Brien had been negotiating with Fox], I remember Conan turning to me and saying, 'I want to do something different.' And it has been," says Ross. "These TBS guys are entrepreneurial; they want to grow the network, they promote the shit out of it, and it's a stable place. A completely different vibe."

Adds Michael Wright, president and head of programming at TBS, TNT and Turner Classic Movies: "An executive's job is not to tell an artist how to make his show. My first note to Conan was, 'Do the show as if no one was looking over your shoulder because, oh yeah, there is actually no one looking over your shoulder.' "

A "lifelong fan" of O'Brien's, Wright says he was heartened when he met with O'Brien in late March 2010 and discovered "he was exactly the guy I'd been watching all those years." Although the network already had George Lopez on in late-night (Lopez would be canceled in August 2011), Wright felt that O'Brien could be the embodiment of what he wanted TBS to become. " 'Yes, this is the voice,' " Wright recalls thinking.

♦♦♦♦♦

Back at Prosecco, O'Brien orders another Pinot. "I'm going to need it to talk about NBC. Also, do you have any black-tar heroin?"

The plan seemed simple enough. In 2004, NBC announced that O'Brien would inherit the Tonight mantle from Leno, who, in 1992, had assumed the throne from Johnny Carson. What no one knew then was that Leno would not retire quietly. Instead, not long before O'Brien made the move to Tonight, it was announced that Leno would fill a new primetime spot at 10 p.m. Seven months into O'Brien's tenure, Tonight's ratings were poor, with much of the blame going to a lame lead-in by Leno (others blamed O'Brien's less-than-broad style of humor). But instead of canceling Leno, NBC Universal president and CEO Jeff Zucker offered a murky solution: Move O'Brien's Tonight to 12:05 a.m., and slide Leno into an awkward 30-minute slot at 11:35 p.m.

Jeff Gaspin, then chairman of NBC Universal Television -- on the brink of acquisition by its now-parent company, Comcast -- announced the decision Jan. 10, 2010; two days later, O'Brien issued the statement that would essentially dissolve his 17-year relationship with the network that had first taken a chance on him: "I sincerely believe that delaying The Tonight Show into the next day to accommodate another comedy program will seriously damage what I consider to be the greatest franchise in the history of broadcasting. The Tonight Show at 12:05 simply isn't The Tonight Show."

On Jan. 21, the network announced that O'Brien had accepted a deal (that reported $30 million) to walk away from Tonight; Leno would be reinstated as host. A day later, flanked by celebrity supporters such as Tom Hanks, Neil Young, Steve Carell and Ferrell, O'Brien ended his Tonight run. The conflict played out largely with the "cool kids" siding with O'Brien and Leno vilified (albeit temporarily).

O'Brien's college buddy and longtime friend Greg Daniels, with whom he worked on The Harvard Lampoon and later on The Simpsons, admits he initially thought O'Brien should "swallow the bad treatment and stay at NBC." Then, says the co-creator of Parks and Recreation who also adapted The Office for American audiences, "I felt really happy for him because I knew he was betting on himself. It was a happy ending to the whole Tonight Show mess."

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More than two years later, O'Brien reveals there still are occasional waves of resentment: "There are moments of, 'What the hell happened? Why did that person do that or say that?' But there's also lot of, 'OK, let's file this under There's A Lot I Can't Control.' "

O'Brien says he's had no contact with anyone at NBC since he left, including ousted execs Zucker and Gaspin (who declined comment), and the head of West Coast operations Marc Graboff, who opted to leave his Comcast contract early, in November. "It helps that almost everybody involved in the craziness has been relieved of their jobs," says O'Brien.

As for Leno, "He certainly isn't calling me. It's not like he's going to sneak up on me in traffic. He's a guy you see coming from a ways off because he's usually driving a car made of copper that runs on manure and has gas lanterns," he adds. "The odds are we will both leave this Earth without speaking to each other, which is fine. There's really nothing to say. We both know the deal. He knows; I know. I'd rather just forget."

O'Brien pauses, then adds: "At a certain point, you're doing yourself and the people you love and work with a disservice if you carry it around. I had an amazing partnership with NBC and was very disappointed at the outcome, but I didn't feel entitled to the Late Show or Tonight or to the TBS show. If you're in this business and haven't experienced profound pain at some point, you're not doing it right. I strongly believe that."

O'Brien is also candid about the challenges he's faced during his reinvention. Yes, he says, Big Bang reruns have helped save his show. Yes, "there's a lot of work to do" in shaping his "shtick" on TBS. Yes, his mantra of "Get better or go away" isn't easy to apply in the war for late-night relevance, especially amid criticism that Conan isn't different enough from his previous incarnations.

The naysaying isn't entirely different from where it was in 1993, when Late Night premiered on NBC and critics deemed it a doomed experiment, saying there was no place among late-night's heroes for a gawky, red-haired Harvard snob with a funny name and a rocky premiere.

"I would say the same thing that I said 20 years ago," says Lorne Michaels, who hired O'Brien in 1987 as a Saturday Night Live writer, then plucked him from the Simpsons writers' room six years later to be the heir to Letterman's Late Night. "He is so bright; he always figures it out. You see him figuring it out now on TBS. It's like watching him during the 2008 writers strike when there was nothing but him on the stage. He doesn't need the elaborate apparatus of a show to be good. At the core of it, he is one of the funniest people on the planet."

Ferrell credits a higher power: "For Conan to re-emerge with his reputation and integrity intact, it's like the comedy gods are taking care of him." Says O'Brien: "I have no regrets about any of it. What has saved me are family, my staff and work. It's not just about me."

♦♦♦♦♦

Two days after his birthday, O'Brien sits inside a makeshift greenroom at the University of California, San Diego's RIMAC Arena. It's a narrow space draped on all sides with black cloth. "Dressing rooms can deflate you no matter who you are," he says. "Bob Newhart once said there's always a piece of brown lettuce on the floor no matter where you go. And, you're always 30 seconds away from an audience who doesn't give a shit."

The latter sentiment doesn't apply to tonight's sold-out event in front of 4,300. The unpaid day trip (O'Brien took the train) is partly a favor for a classmate of his from Harvard, Elizabeth Losh, who works at the university.

Many in the crowd are dressed in "I'm With Coco" and "Conan O'Brien College" T-shirts (the university named one of its schools after him for the day), and the buzzy anticipation isn't lost on O'Brien, all casual-cool in a slick brown leather jacket, navy shirt and black slacks. Sipping a Diet Coke, studying material he has written on note cards, he sits in a low squat like a sprinter before a 100-meter dash. His eyes are closed, and the microphone is pressed to his forehead, as if he's exchanging mental notes with the device. At 6:10 p.m., the provost of the university beckons O'Brien to the stage.

"UCSD, I can't hear you!" shouts O'Brien as the crowd explodes in a rock concert-like frenzy.

Pacing back and forth like a gospel preacher, he announces a few promises for his 24-hour tenure as head of Conan O'Brien College. "I will make alcohol free! Pot will be mandatory!" screams O'Brien above the din as it becomes clear that many in the crowd have indulged in both before the event.

He doesn't miss a beat during the Q&A when a charming nerd asks for love advice ("Is she here tonight? Do you want me to call her?" he offers). He politely declines to reveal the number of women he has been with sexually (not many, he admits), fields several inquiries about his hair and erstwhile beard (he lets one woman run her hand through his amber follicles) and, 43 minutes in, invites a giddy young woman to sit next to him onstage, a moment that ends with her accidentally, and harshly, ramming her head into O'Brien's. "That's OK; I'll be fine … there are other celebrities out there. You'll take care of my kids when I'm gone, right?" he asks the girl, who quakes with delight.

"I always tell my wife, 'If I ever have a disease, put me in front of a crowd of college students," says O'Brien. "They will be my cure.' "

That night, a tired O'Brien, with one hell of a hoarse voice, talks about how much he enjoyed visiting with students, many of whom reiterated how much his farewell Tonight speech had meant to them. "I'm asking this particularly of young people that watch," he said in that somber final broadcast in January 2010. "Please do not be cynical. I hate cynicism; for the record, it's my least favorite quality. It doesn't lead anywhere. Nobody in life gets exactly what they thought they were going to get. But if you work really hard, and you're kind, amazing things will happen."

He adds: "When I hear those kind of stories, I think, you know, it was all worth it."

♦♦♦♦♦

THE NBC EXECS: WHERE ARE THEY NOW?

Jeff Zucker, former president and CEO, NBC Universal -- The exec at the center of the Leno-O'Brien brouhaha was fired by Comcast CEO Steve Burke in September 2010. Zucker, who exec produced NBC's Today for eight years, is EP on Katie Couric's talk show, Katie, bowing Sept. 10.

Jeff Gaspin, former chairman, NBC Universal Television -- He served in the position for less than a year before resigning in November 2010 amid the Comcast-takeover reshuffling. Now he serves as president of Gaspin Media, a full-service production and media consulting company.

Marc Graboff, former president of West Coast business operations, NBC Universal --  The last top player from the Zucker era to leave, Graboff, now based in New York, heads CKX, parent company of 19 Entertainment (American Idol, So You Think You Can Dance?) and controller of Elvis Presley Enterprises.

♦♦♦♦♦

HOW THE SHOWS STACK UP: Since December, Conan has gained viewers while their ages have fallen.

Conan (TBS) -- Mon-Thu, 11 PM

  • Median Age of Viewer: 35
  • Viewers per Episode: 1.1 million

Chelsea Lately (E!) -- Mon-Thu, 10 PM

  • Median Age of Viewer: 37
  • Viewers per Episode: 942,000

The Colbert Report (Comedy Central) -- Mon-Thu, 11:30 PM

  • Median Age of Viewer: 41
  • Viewers per Episode: 1.8 million

The Daily Show With Jon Stewart (Comedy Central) -- Mon-Thu, 11 PM

  • Median Age of Viewer: 43
  • Viewers per Episode: 2.6 million

The Late Late Show With Craig Ferguson (CBS) -- Mon-Fri, 12:35 AM

  • Median Age of Viewer: 52
  • Viewers per Episode: 1.5 million

Late Night With Jimmy Fallon (NBC) -- Mon-Fri, 12:35 AM

  • Median Age of Viewer: 52
  • Viewers per Episode: 1.8 million

Jimmy Kimmel Live! (ABC) -- Mon-Fri, 12:05 AM

  • Median Age of Viewer: 53
  • Viewers per Episode: 1.7 million

Late Show With David Letterman (CBS) -- Mon-Fri, 11:35 PM

  • Median Age of Viewer: 55
  • Viewers per Episode: 3.4 million

The Tonight Show With Jay Leno (NBC) -- Mon-Fri, 11:35 PM

  • Median Age of Viewer: 58
  • Viewers per Episode: 3.8 million

Source: Nielsen

♦♦♦♦♦

CONACO'S BUSY SLATE: O'Brien and Jeff Ross' production company has several shows in production and development.

Doen Cole's Black Box

On May 10, Turner announced a six-episode order of this Tosh.0-esque clips series hosted by Emmy-nominated Conan writer Deon Cole. It is slated to premiere in 2013 on TBS.

Eagleheart

Chris Elliott stars in this 15-minute Adult Swim black comedy, in its second season, about a Chuck Norris-like police ranger and his posse -- if Norris were a total idiot and his posse were vacuous dummies.

The Flaming C

Conaco is working on a pilot for an animated series based on a muscle-bound superhero version of O'Brien created by his writers. The company plans to shop the project, produced in partnership with Warner Bros. Animation.

Super Fun Night

This scripted comedy pilot for CBS is filming in Los Angeles and stars Australian Bridesmaids scene-stealer Rebel Wilson as leader of a gaggle of geeky women in pursuit of fun on Friday nights. SNL alum Jenny Slate (Bored to Death) and Groundlings performer Edi Patterson co-star.

IN DEVELOPMENT

Most Likely

Created by writer-producer Josh Heald (Hot Tub Time Machine), this comedy centers on a star student returning home after 10 years who's forced to work for the jock who ruled high school, also with Warner Horizon.

Zone Lord

Three roommates discover an alien has moved into their building in this comedy created by writer-producer Ross Venokur (The Tick) and in partnership with Warner Horizon Television.