The War for Late Night by Bill Carter
One of the main reasons that The Late Shift was so compelling at the time was the internet's infancy meant most people (anyone who didn't subscribe to the New York Times) were reading Bill Carter's behind-the-scenes accounts for the first time. This time around, Carter was on top of every Conan/Leno development as they happened, and likewise anyone with internet access could essentially follow the behind-the-scenes ups and downs in real time as he was publishing numerous stories on the Times web site daily.
The draw of Carter's book is his ability to flesh out the private conversations and characteristics of the key players. Leno isn't a calculating villain as much as he's simply oblivious to anything other than himself. (He utters the mantra "I tell jokes at 11:30 at night" so often that you wonder if he values any other skills in himself.) Conan seems retroactively doomed from the start of things, oblivious to any issues until he was already on his way out.
And then there are the NBC execs. Jeff Gaspin comes off as the most sensible, noting that Conan had turned off a significant number of his Late Night fans (winning them back only when he went for broke the last couple weeks), while failing to attract the broader audience. Jeff Zucker avoids becoming the true antagonist of the book, but only because his shortcomings as an executive and human being are easily trumped by Dick Ebersol. Early in the book, it's pointed out that Conan delivered a handwritten touching letter when Ebersol's son was killed in a plane crash. Throughout the rest of the book, Ebersol acts like a complete asshole, treating O'Brien as a dumb rube for not taking his notes on "improving" the show, and bitching about Pearl Jam playing on his first show. (What's that? An out of touch 62-year-old man doesn't think Pearl Jam are a musical draw? Perfect.) For a guy whose main professional achievements include installing Colin Quinn as SNL Weekend Update anchor, and overseeing an Olympic games that lost "a couple hundred million bucks" for NBC, this guy sure gets upset at people who ignore his terrible advice.
While the mindset of Conan and Jay throughout is fleshed out, it's obvious that Carter was never able to talk to Letterman, as any quotes from Dave are taken directly from Late Show broadcasts, but of course it's unlikely he'd get anything better than this either way.
As far as on-air talent goes, Jimmy Kimmel ends up coming off best. He pointed out to Letterman that he thought Dave threw Jay a life preserver with the Super Bowl ad. And of course, there was this, which can't be seen enough times. WHAT'S THE BEST PRANK YOU EVER PULLED?
Carter's epilogue features an interview with Jerry Seinfeld, who says "What did the network do to him? I don’t think anyone’s preventing people from watching Conan. Once they give you the cameras, it’s on you." This point is entirely correct, though of course it's odd to hear Jerry Seinfeld using this line of reasoning, considering it took four seasons for Seinfeld to become a hit show. Had NBC followed his logic, it would have been pulled after one. But I suppose that would have been his own fault?
From my point of view, the best all-encompassing summary of The Tonight Show with Conan O'Brien comes not from The War For Late Night, but from Louis CK, who hit the nail perfectly on the head.
When Letterman really wanted 'The Tonight Show' I didn't understand it because he has his own show called 'Letterman.' And when they rejected him he went and got 'Letterman' again. He's doing great. Conan had 'Conan.' Nobody really called it 'Late Night' that's how much he had made it his. That was 'Conan.' And I don't know why he'd want to give that up to host 'The Tonight Show,' which is just this old, shitty thing. Let Jay have it. It's a little presumptuous of me to tell Conan that his dreams are misguided... but they are."
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