Q. You are David Letterman. How do you beat Conan O'Brien's Tonight Show in the ratings?
First of all, these can't be good times for Dave. His grudge against Leno was real and enduring, and if he softened a little bit recently that doesn't mean he didn't retain a competitive nature. The sweet revenge of outlasting Jay at 11:30 (well it's 10:30 Central for me, and has been my whole life) is undercut by the weird-and-possibly-doomed deal Jay just cut for his primetime experiment.
Meanwhile, Letterman finds himself in the unprecedented situation of not having the most critically respected talk show in his time slot. Does he care? I remember when a beef flared up over ratings and Letterman's producer said:
There are two parts of the so-called late-night war. One is: who's the best. That part of the war is over. Dave won.Could he say that against Conan?
Well, maybe. Maybe Conan's show simply won't work at the new time. The quirk and surrealism that were Conan's calling cards at Late Night could be flattened out by the demands of the Tonight Show franchise. I don't think that's what's going to happen, and apparently neither does Conan. But you never know. Ratings are unpredictable and my understanding is that network execs can be nervous people.
In that case, Letterman probably just does what he's been doing and no matter what the ratings he wins because he's never taken any guff from anybody.
But let's say you're David Letterman and you really want to make a play for ratings dominance now. Here is the option that interests me: What if Dave decided to, as it were, run to Conan's right? Can he turn himself into the ratings-winning Leno to Conan's critical-darling Letterman?
Consider: Conan is young. He's weird. He's hip. That might not be the best way to build an audience at 11:30. How can Letterman go about targeting some of the ex-Leno-viewers who don't cotton to Conan? Could he woo them by doing more lame, Lenoesque gags and fewer strange, Lettermanesque stunts? It seems to me that this could work. Of course the risk is that you make your show lamer and then you still don't win in the ratings.
To be honest, I'm not sure at this point how much Letterman really cares -- he could buy an island nation with his "Everybody Loves Raymond" money alone. But let's say he did. What would be his best shot at beating Conan?