Conan O'Brien's Work in Progress

Business Week

The former Tonight Show host is in play, but prospective TV and cable networks are struggling to find him the right time slot

Illustration by Jim Cooke

The last time America saw Conan O'Brien, the red-haired, late-night talk show host was riffing on an electric guitar as comedian Will Ferrell donned a shoulder-length blond wig to screech his way through the Lynyrd Skynyrd song Freebird. As final shows go it was an appropriately wacky end to NBC's high-profile firing of O'Brien from The Tonight Show. Celebrities denounced NBC. Pro "Coco" fans demonstrated outside the studio.

So you'd think landing another major TV gig would be a snap, right? Actually, no. Since leaving the air on Jan. 22, O'Brien has been flitting from one potential deal to another as network and cable executives struggle to find the right programming slot for his show. Fox wants him for its 11 p.m. slot but hasn't yet convinced its TV affiliates—or even the stations owned by corporate parent News Corp. (NWS)—they should carry it. A 7 p.m. syndicated show against the likes of Jeopardy! or Entertainment Tonight is possible, as is a show on cable, but both face big challenges.

"Getting Conan is a once-in-a-generation opportunity to get a well-known talent with a following," says Bill Carroll, director of programming for Katz Television Group, which advises TV stations on licensing shows. "But the timing couldn't be worse. Every scenario for him has more risks than upside."

Late-Night Crowd

O'Brien's most daunting problem is breaking into a late-night lineup that has grown overcrowded in the last five years. A new show would have to compete against NBC's Jay Leno, CBS's (CBS) David Letterman, and ABC's Nightline. And younger viewers who might flock to O'Brien are instead watching shows like Comedy Central's The Colbert Report or Family Guy on the Cartoon Network's Adult Swim, says Brad Adgate, head of research for the TV ad-buying company Horizon Media. Some of Fox's larger stations meanwhile are airing The Office reruns and have signed expensive deals for reruns of NBC's hit show 30 Rock in some of those late-night time slots.

Fox Entertainment President Kevin Reilly enjoys a strong relationship with O'Brien, with whom he worked while both were at NBC. But Fox first needs to persuade its affiliates to take a chance. "It's been a very challenging environment for the station business coming off a recession," Reilly says. And he acknowledges that if he can strike a deal with affiliates it could take several years to stitch together a single time slot because some stations will continue to run sitcoms after their news programs. One strategy might be to start the show at 11 p.m. in some markets and later in others, according to TV executives with knowledge of Fox's options. News Corp. could also air O'Brien on some of its less watched affiliate group MyNetworkTV's stations in New York, Chicago, and elsewhere. With shows like Glee and The Cleveland Show, Reilly has boosted Fox's ratings by 3% this year and leads in the sought-after 18-to-49-year-old age group. O'Brien would help extend Fox's edgier brand to late night as well, says Horizon's Adgate.

Not everyone at News Corp. agrees. Fox's syndication arm, which sells reruns of The Simpsons and other shows, could lose a late-night market to O'Brien. And Fox-owned stations would likely be forced to swallow losses for reruns they've already licensed. "We're giving it a lot of thought," CEO Rupert Murdoch said in a February conference call. "If the program people can show us that we could do it and be fairly confident of making a profit on it, we'd do it in a flash."

Starz, Showtime Talks

Fox is unlikely to spend the $50 million a year that NBC spent to produce The Tonight Show, say two sources with knowledge of the talks, or to pay its host's $12.5 million salary. O'Brien, who together with his staff left NBC with $45 million in network severance, has been looking for places other than Fox to yuk it up. Team Conan, which includes manager Gavin Polone and William Morris Endeavor Entertainment agent Rick Rosen, has chatted up pay cable channels Starz and Showtime on deals similar to the show Bill Maher hosts on HBO, three sources with knowledge of the talks say.

O'Brien is also considering taking his shtick to an earlier hour. CBS's syndication unit, which distributes Jeopardy! and Wheel of Fortune, has talked with him. So has Debmar-Mercury, a unit of Lions Gate Entertainment (LGF) that syndicates the game show Family Feud and sitcom Tyler Perry's House of Payne, which wants him for 7 p.m. That hour might appeal to O'Brien, who wouldn't face the prospect of coming in fourth in the late-night wars. But a comedy-style talk show has never worked in that time slot, according to Katz Television's Carroll. That's why Sony (SNE) considered, then passed, on the idea.

Leno says he expects O'Brien to return to late night. "He'll come back, and he'll be strong," he told The View co-host Joy Behar in a video interview she posted on the Web. On Apr. 12 a newly bearded O'Brien will begin his 30-city The Legally Prohibited from Being Funny on Television Tour. For now, says Polone, the comedian is "not thinking of anything except opening the tour with the strongest show possible."