Remember when Conan O’Brien was the host of The Tonight Show?

It occurred back in 2009, back when the Shattered Lens was just starting out.  After hosting the show for 17 years, Jay Leno stepped down as host of The Tonight Show.  Though he was never popular with critics and I don’t think I’ve ever met anyone who actually made it a point to watch him, The Tonight Show with Jay Leno was the number one in the late night ratings.  David Letterman may have had more cultural cachet but Jay Leno was the host that most late night viewers were watching.  Other comedians may have mocked Leno for his safe and non-controversial hosting but, obviously, it worked.

When Leno first left The Tonight Show, no one was surprised by Leno’s retirement because he had announced it five years earlier.  In 2004, NBC renewed Leno’s contract as host with the condition that Leno would step down in 2009 and that Conan O’Brien would become the new host of the Tonight Show.  The fear was that, otherwise, Conan would switch to another network and compete directly against Leno.  At the time, Leno privately complained that he felt he was being fired but, publicly, he announced that he was happy to hand the show over to Conan in 2009.  In words that would come back to haunt him, Leno announced, “It’s yours, buddy!”

In 2009, Conan took over last night while Jay Leno got his own primetime talk show, which aired every weeknight.  It was an odd arrangement, one that was undertaken to keep Leno from going to another network.  (NBC was apparently very paranoid about its talent hopping to to other networks.)  Not only did NBC have to rearrange its schedule to make room for 5 days of Leno but many observers suspected that the whole thing was essentially some Machiavellian network scheme to eventually once again make Leno host of The Tonight Show while destroying Conan’s viability as a potential competitor.  Regardless of why NBC did what they did, it didn’t work out.  Leno’s primetime ratings quickly tanked.  So did that ratings for The Tonight Show with Conan O’Brien.  O’Brien’s supporters said that Conan’s bad ratings were due to Jay being a bad lead-in.  Jay’s supporters said that Conan just wasn’t ready for the 11:30 slot and that Conan’s ratings had been going down for a while.  And while most television critics sided with Conan, NBC obviously sided with Jay, who had always been viewed as being a good and loyal company man.

NBC’s solution to the problem made about as much sense as any of their other actions.  It was announced that Jay would have a new late night show, a thirty-minute variety show that would air before The Tonight Show.  The Tonight Show would be bumped back by half-an-hour.  O’Brien objected to getting stuck with a later start time but it turned out that his contract gave NBC the right to move the show back by 30 minutes.  O’Brien resigned, writing an open letter to “the people of Earth,” in which he said that he would not take part in the “destruction” of The Tonight Show.  Depending on which side you were on, Conan was either being heroic or overdramatic.

How big was this story?  It was so big that even I knew about it, despite the fact that I didn’t watch any of the late night shows.  It was one of the first big cultural conflicts that I can remember blowing up on Twitter.  Twitter was almost 100% pro-Conan.  Meanwhile, Leno’s supporters tended to be older, they tended to not have much use for social media, and they tended to be a bit more pragmatic.  Jerry Seinfeld sided with Jay, saying that the only problem was that Conan wasn’t getting the ratings.  Jimmy Kimmel very publicly sided with Conan.  David Letterman let everyone know that they were now seeing the Jay Leno that he had always known.

It was a mess and no one came out of it untouched.  Leno returned to hosting The Tonight Show but his reputation with now irreversibly tarnished.  Conan moved to TBS and, while the critics respected him and his fans continued to love him, he never quite regained the cultural prominence that he had before The Tonight Show debacle.  Most of all, NBC came out of it looking worse than ever.  The entire reason for Jay’s early retirement announcement was to avoid conflict and controversy.  Needless to say, that didn’t work out.

Looking over it all, one can’t help but wonder how a group of industry professionals, people with television experience who were paid to know what they were doing, could have so dramatically screwed everything up.

Bill Carter’s The War For Late Night is probably the best place to look for the answer.  Published in 2010, mere months after Leno replaced Conan as the host of The Tonight Show, The War For Late Night provides an insider’s look at what went down in the corporate offices of NBC as well as what was happening in both the O’Brien and the Leno camps.  Carter also examines what was going on with the other late night hosts while O’Brien and Leno was battling for the future of Late Night.  The book deals with the unsuccessful attempt to blackmail Letterman (remember that?) and also provides an interesting reminder of how likable Jimmy Kimmel was before he got all self-important.

Though Carter appears to be Team Coco, the book itself is relatively even-handed.  Leno is not portrayed a monster and Conan is not transformed into a saint.  (Indeed, the books makes clear that the real villains were the NBC executives, who first screwed Leno by forcing him out when he was at the top of the ratings and then screwed Conan by refusing to give his version of The Tonight Show time to grow.)  Instead, the book suggests that the main reason for the conflict between the two hosts was that Leno and Conan had two very differing ways of looking at their job as host of The Tonight Show.  Jay viewed it as a job.  Conan viewed it as almost a holy calling.  In the end, Jay was incapable of understanding why Conan was so upset about what was happening while Conan couldn’t understand how anyone couldn’t be upset.  After reading Carter’s book, it seems like a foregone conclusion that NBC would side with Jay.  Management always prefers an employee who doesn’t make waves compared to one who does.

Towards the end of the book, when David Letterman tries to arrange for Conan to appear in a Super Bowl commercial with him and Jay, Conan snaps that Letterman doesn’t understand how upset Conan still is over what happened.  Conan says that he will never be ready to laugh about it and, having read The War For Late Night, you don’t doubt it.  The book succeeds at both explaining what happened and also revealing the human beings behind the conflict.  In the end, even if you understand Jay’s position, your heart breaks for Conan.