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Bill Simmons, ‘the Sports Guy,’ Saw Talkshowgate Coming, and Now He’s Got Advice for Conan

The news that Conan O’Brien would be leaving the Tonight Show was broken by an unlikely source at the end of last week: a tweet from ESPN’s Bill “the Sports Guy” Simmons, which read, “FYI: Next week is Conan's final week hosting the Tonight Show. His staff is trying to book big guests so he goes out with a bang. It's true.” Within hours, NBC was confirming it. Simmons had it first.

For a sportswriter, Simmons knows his late-night talk shows. He was one of the charter writers for Jimmy Kimmel Live — he and Kimmel remain close friends — and back in March, he accurately predicted that Jay Leno would be back in the Tonight Show chair “within a year.” With that kind of track record, we couldn’t resist asking him if he had any advice for Conan, any guesses on the next turn for this story to take, and any predictions on how this will affect his pal, Kimmel.

Do you think Conan worked at 11:30? Do you think if he goes to Fox, he should do the same show? The old show? An entirely new beast?
Conan's show sucked at 11:35. That's the reason the ratings were down — not because of his lead-ins. What's Jon Stewart's lead-in? What's SNL's lead-in? Conan did a watered-down, toothless version of his 12:35 show, and even his die-hard fans weren't crazy about it. These are the facts. Only after they canned him did he show flashes of the old Conan again. Look, he's not Johnny Carson; he's a gawky, super-witty, awkward, hyperactive goofball who isn't going to appeal to everyone. I don't see Fox at 11 working, either. We just saw him fail at 11:35 ... Going head-to-head for the egghead demo with Jon Stewart [at 11] will be better? If he were smart, he'd go to Comedy Central at 12, follow Colbert and Stewart, and just be himself.

Do you think Conan handled this situation the right way?
I thought he was too whiny. Look, it's television. His job was to deliver ratings and revenue; he lost nearly 50 percent of Leno's 11:35 audience in six months, but took none of the blame and made no effort to fix his show. This wasn't his fault? And besides, he's the one who stupidly passed up all that Fox money in 2004. I never understood that. What was so special about a Tonight Show that had twelve years (and counting) of Leno stink on it? How iconic could it have been? Plus, it was foolish of him to think Leno would fade into the sunset in 2009. We're gonna have to chop Leno's head off like Jason Voorhees to get him off TV.

Related: Who Were the Winners in the Late Night Wars? [NYM]

Does it really hurt Leno if the commentariat dislikes him? The people who have made him so popular probably aren't paying any attention to this in the first place.
Yes and no. He dumbed down his show intentionally knowing he'd win the ratings game that way. And he did. You're right, his audience could give a crap: They're too busy applying to be on the next Hoarders. But that same audience splintered when he abandoned that 11:35 slot. Some stayed with Conan, others went to Colbert, Nightline, SportsCenter, online, wherever. Once people stop getting in the habit of seeing you, it's hard to get them back. By the way, the same goes for hookers.

Isn't this all kind of silly? Isn't the theory that everyone just watches everything on Hulu and DVR anyway?
Normally, I'd agree with you, but did you see the numbers? Leno's 11:35 show made $35–40 million profit for NBC; Conan's show was on pace to lose $5 million and had zero critical buzz. So it was a big deal, I think; look at where Conan was five years ago and where he is now. It's one of the biggest falls in TV history. NBC paid $43 million to get rid of him! It was the TV version of the Knicks buying out Stephon Marbury last year, only without tattoos, Kathleen Decker, and a truck party. Anything that leads to a legitimate Conan-Marbury comparison has to mean ... something. Right?

Related: Who Were the Winners in the Late Night Wars? [NYM]

Photo: Photo Illo: Mary-Louise Price; Photos: Bill Winters/Getty Images, iStockPhoto, ESPN.com