With all the hubbub this week re: Jimmy Fallon finally ascending to the role of “Tonight Show” host on NBC, I read Bill Carter’s 2010 chronicle of the last disastrous “Tonight Show” host transition, “The War for Late Night: When Leno Went Early and Television Went Crazy.”  In my mind, it’s the equal of Carter’s earlier book about the late night wars “The Late Shift,” and one of the best books about show business ever written … with an emphasis on “the business” part of that phrase.  It’s a great primer on why “win-win” solutions that look good on paper oftentimes result in disaster.  And it’s the perfect illustration of that old cliche: “You can’t have your cake and eat it too.”

Let’s go down memory lane to the early 2000s… and forgive me if I’m skipping over several key events because I don’t want this to sidetrack my main point:  Jay Leno’s “Tonight Show” was at the top of the ratings for late night talk shows.  However, Conan O’Brien, who hosted the show that came on after the “Tonight Show” (“Late Night”), was scoring bigger ratings among younger viewers, the most prized demographic for advertisers.  It’s the reason why the “Red Skelton Hour” (a Top 10 show) was dropped by CBS in the early 1970s, because the audiences were not the type that brought in big advertising dollars.   Other networks noticed Conan’s appeal among younger viewers  and offered him as much as $20 million a year to leave NBC.  As a result, NBC was desperate to keep Conan. 

At the time, NBC wasn’t about to pay that kind of money to keep Conan (Jay still earned less than $20 million per year), but they had a huge ace up their sleeve:  Conan’s dream of hosting the “Tonight Show” one day.  They did not match what other networks were offering Conan dollar-wise, but agreed to give Conan the “Tonight Show” in 2009, in order to extend his stay at “Late Night” further … with a huge financial penalty (approximately $45 million)  if NBC reneged.  Conan readily agreed.   First problem solved.

Second problem?  What to do about Jay.  Jay was not only scoring the highest ratings in late night, but he genuinely loved his job hosting the “Tonight Show” and most importantly, was in no hurry to leave.  Like Conan, Leno could have made a lot more money going elsewhere (David Letterman’s salary was substantially higher on CBS), but stayed on as the “Tonight Show” host because of his genuine love for the prestige such a gig had.  They told Leno they would extend his contract, but with the agreement in 2009 that he would step down.  The decision hit Jay like a sledgehammer to the gut.  He warily agreed, but started making his resentment clear by making sharp remarks about the situation in his “Tonight Show” monologues and started negotiating behind the scenes to go to another network.

The suits at NBC panicked.  While they wanted to keep Conan, they didn’t want to lose Jay to another network and have Jay potentially come out on top elsewhere.  Their solution?  To give Jay a 10:00 pm show where he could still do his monologue and other comedy bits, but Conan could keep the “Tonight Show.”  Since NBC was in the ratings cellar, moving Jay to 10:00 pm five nights a week, even with paying him more money per year, was substantially cheaper than developing and producing five new dramatic shows.  Plus, since Jay’s audience was skewing older, it made sense at the time to put him in prime time.  The solution first struck both Jay and Conan as unorthodox, but they agreed.   The decision was announced with much fanfare and the NBC suits appeared to be geniuses, averting the ugliness that prevailed in 1993 during the prior “Tonight Show” transition between Johnny Carson and Jay.  Ah … but reality has a funny way of spoiling the best laid plans.

The reality?  Jay’s show bombed at 10:00 pm.  While Jay’s new show was not that radically different than his old “Tonight Show,” it became clear that what works in one time slot may not work well in another. Affiliates were up in arms over the low ratings and threatened to yank the show off their stations.  Conan, on the other hand, was doing merely OK on the “Tonight Show.”  While he was still pulling in the more prized demographic, he was losing in overall viewership to Letterman’s show, which was on top for the first time in several years.  The suits proposed moving Jay’s show to 11:35 pm and moving Conan’s show to 12:05 am.  Jay agreed, but Conan balked.  Yes, Conan would still technically be hosting “Tonight Show,” but it would be on at 12:05 am … rendering the title “Tonight Show” technically meaningless and in Conan’s mind, diminishing the prestige and history of the long-time late night show.

I should point out the fatal flaw Conan’s team made in signing their contract.  While Conan was specifically given the “Tonight Show” in his contract, there was no time-slot protection, a major clause in all major late night host’s contracts.  Which means that NBC could technically stick the “Tonight Show” almost anywhere in the schedule and they would still be in compliance of their contract.  Conan was not pleased with things, but was still mulling things over when NBC made a fatal mistake.  Desperate to get Conan’s thumbs-up before an affiliate’s meeting, NBC head Jeffrey Zucker started playing hardball with Conan’s team. That, plus the fact that Conan’s team was literally the last to know about these plans (even Jimmy Fallon, who took over “Late Night” after Conan went to the “Tonight Show,” knew of this plan before Conan did), finally, in Conan’s words, cured him of his “Tonight Show” addiction.

As we all know, things got extremely ugly amongst all parties involved.  Jay’s fans wondered why Conan would be making such a big deal about doing his show 30 minutes later.  Conan’s fans painted Jay as the Baby Boomer who stayed too long at the party and refused to get off the stage.  And remembering the Machiavellian way Jay … or his management team at the time … beat Letterman for the “Tonight Show” gig in 1993 indicated this was another example of Jay’s treachery.   Conan’s side definitely got the most favorable press at the time and for good reason: Conan was treated abysmally in this situation by NBC and Conan did have a good point about the new plan diminishing the legacy and history of the “Tonight Show.” But objectively, Jay was not the bad guy in this situation either.  As Jay indicated, there was another side to this story: the older guy who’s doing well in his job, but is asked to step aside by the bosses at the top to make way for someone younger.   Jay’s grumblings about going elsewhere during the “lame duck” period between 2005 and 2009 is perfectly understandable.  And NBC trying to find a solution to keep Jay in the fold does make sense, especially since Jay could have potentially done very well going elsewhere.

To be fair to the much maligned Zucker, the initial solution to keep Jay on NBC by giving him a 10:00 pm show was not hastily decided.  The decision did make a lot of sense based on the research they conducted and the network’s financial realities.   And, had both Jay’s and Conan’s shows had more time to work out their bugs and get into a groove, there’s a possibility both shows may eventually would have survived and thrived.   But affiliates were losing viewers and money, and their threatened boycott did not allow enough time for this to happen.

As we all know, a solution was worked out between all parties, but resulted in a lot of bad feelings.  Carter’s account of this debacle  (which includes many other fascinating subplots and characters) is a terrific examination of how pleasing everyone oftentimes leads to pleasing no one.