The Power of 11:30: On "The War for Late Night" by Bill Carter

I'm still trying to get my old reading groove back, which was, for better or for worse, altered permanently by law school. I'm only recently easing my way back into my old habits of enjoying sentences, taking my time, and not feeling like highlighting everything in preparation for a recitation or an exam. Reading a new book with the purpose of writing a review about it - instead of being quizzed on it - hopefully readjusts my lenses.

When I was a teenager, one of the biggest perks of finally sleeping in my own room was getting to stay up late. Back then, getting lost in the peculiar algorithms of YouTube was not a thing yet. Instead, what excited me the most was getting to catch all these "adult" shows on cable which, at the time, were beginning to be understandable to me. Adult Swim, Sex and the City, and yes, the three late night shows: Late Show with David Letterman, The Tonight Show with Jay Leno, and Late Night with Conan O'Brien.

Late night shows were a particularly endearing breed for me. It had celebrity interviews, sure, but the real draw was the personality behind the table. I've always taken these shows at face value and liked them for the different flavors each one gave. Dave, for his sardonic, cynical humor especially in his Top Ten. Jay, for his rapid-fire monologue and Headlines. And Conan. Oh Conan. I learned the words "shenanigans," "moral outrage," and "noches de pasion" because of Late Night. I had the softest spot for him even when he was the one that most confounded me. He was too quick, too sharp for fifteen-year-old me, but it was always a delight trying to catch up with him and be in on the ride.

When the whole Tonight Show controversy erupted in 2010, I followed it obsessively online. At the time, none of my other friends watched these shows, so it felt like this devastating blow that I couldn't share with anyone. I liked Jay, sure, but the whole shake up was not a good look on him at all. It only solidified what I've always felt through the years: Team Conan all the way. He wasn't given enough leeway with his version of the Tonight Show. And it was so unfair.

After that, the late night scene was no longer the same. Since then, new players have come into the fray. Fallon, Meyers, Corden, Colbert, Kimmel, Noah - these guys are now holding the fort. But the format has changed in so many ways - and necessarily so, given the changes in technology and the way audiences consume media. They now have more sketches and gimmicks, and rely on the virality of each individual segment rather than the cohesiveness of one whole show. Which isn't entirely bad, per se. I do like their content too. It's just different.

Which, I guess, is why I felt the need to read this book when I got an epub copy. I wanted to know what really went behind the scenes, what changed the network's mind, and at what point NBC realized that the late night landscape was going to be significantly shaken again. (Incidentally, I was also really curious to know how the contracts were drafted in the negotiations.)

It's quite ironic that all this went down precisely because they were trying to avoid the exact same thing that happened between David Letterman and Jay Leno back in the 1990s, following Johnny Carson's retirement from The Tonight Show. In the early 2000s, NBC wanted to have a "Prince of Wales" succession clause to secure the person who will "inherit" the throne of The Tonight Show and avoid any drama. The idea was brilliant and the identity of who the successor will be was clear: Conan. What did them all in was the timing.

I'll save you the trouble of reading the book and just refer you to the Wikipedia page linked above if you want to know the timeline of how it all went. But more than just the narration of events, what stood out more in the The War for Late Night was the very personal, and authentic depiction of the actual people involved in the fray. The network executives, the agents, the producers, even the competition at the time. (There's a great chapter on Letterman, but also a recognition of the other key players like Kimmel, Fallon, Colbert, and Stewart.) Most importantly, Conan and Jay.

I've always been Team Conan. He's loved by all, from young intellectuals to fellow comedians and artists. I love the guy, I admire the guy, I binge-consume any content of his that I can get my hands on (Podcast? check; Late Night classics? check; interviews on YouTube? check; Conan without Borders? check.) And the book is actually very sympathetic towards him, showing that in many ways, he really was the victim here. Many other factors were at play: the timing, the ratings, the lead-in, the bind that NBC head Gaspin was in considering the network's descent from the ranks. But it still all boils down to the fact that NBC didn't want him enough. They didn't want him to go elsewhere, but they were willing to break a promise made to him just to make more money. He didn't deserve to have The Tonight Show taken away from him like that.

But, the book also did a good job of showing Jay's side. He's a no nonsense kind of comedian. He wasn't innovative, he wasn't a genius. He didn't go to Harvard like Conan. But - and this is crucial - people loved him. He didn't appeal to the intellectuals, sure, but he is certainly well-liked by even the simplest of folks in Nebraska. He had mass appeal. And to top that off, he worked hard. Really hard. He didn't play into the celebrity schtick, he didn't mind not winning awards. He ran The Tonight Show like a ship, and it always landed at the same place: the top. He consistently beat Letterman in the ratings, something Conan couldn't do. You can't fault the network for wanting to give the keys back to him, especially after the variety show they offered him did not work.

Conan got a shitty lead-in during his stint at The Tonight Show because the network botched it with The Jay Leno show at 10:00 pm. But the fault here is to be placed squarely on the lawyers. Jay had the leverage between the two of them because his lawyers were able to secure for him a "pay-and-play" contract, as opposed to the usual "pay-or-play" (which was what Conan had). This contract guaranteed NBC would both air his program and pay him for up to two years, whether the program continued or not. This is completely different from Conan's The Tonight Show contract, which provided that NBC can either play his program for two years or pull the plug on the show and just pay him off, by network prerogative. Comparing both, NBC stood to lose more if they broke the contract with Jay than with Conan. The pay-and-play was unusual in the TV setting at the time, and there was no way Conan's lawyers could have anticipated that that was possible, because it wasn't an industry standard. But Jay's lawyers did. So his ass was saved by the network instead.

The book was published in 2010. Reading it now, in 2020, it's easy to say that Conan still eventually got the better end of the deal in the long run. Sure he never got to fully enjoy his tenure as the host of The Tonight Show. But he was able to diversify his content: he got to set up his own production company, has a podcast, shoots for a Netflix docuseries, has mockumentary shorts involving his staff, and still has a late night talk show, albeit on a cable channel now. He has the freedom to do whatever he wants, and that has only resulted in more hilarious, genre-bending, and entertaining content since then. In particular, his podcast and travel series show a different side of him, one that allows him to flesh out his conversations with his interviewee because he has more time to breathe and just be. The interviews he does now no longer focus on just, say, promoting a movie, or rehashing an oft-repeated anecdote. He has the opportunity to really get to know them, find out their stories, and all while sharing a little part of himself. Even in other forms of media, he's still somehow changing the game.

But at the same time, I can't help but wonder - what could have been? If he had remained at The Tonight Show, I think he would have eventually veered towards the same content (aimed at virality), while still maintaining his identity. Breaking the norms, making people uncomfortable, finding the silver lining even at the perverse. He may not be doing a Lipsync Battle or Carpool Karaoke - but I think audiences would have loved an updated Triumph the Insult Comic Dog just the same. He could have been breaking even more barriers, given the timeslot's reach.

Alas, it wasn't meant to be. And as with most things, we have no other choice but to look at it as a glass-half-full kind of situation. The late night format as we knew it had to end somehow. It was just unfortunate that it had to claim one of the greats as its victim.

One of my favorite post-Tonight Show Conan content though, is his speech for the 2010 graduating class of Dartmouth. It has all the ingredients of everything Conan: hilarious, ridiculous, well-researched, self-deprecating, and full of wit. But what stood out about this speech - and what makes me re-watch it from time to time - is his honesty. And the ability to turn his heartbreak into a catalyst for something more meaningful.

There are few things more liberating in this life than having your worst fear realized.
It is our failure to become our perceived ideal that ultimately defines us and makes us unique. It’s not easy, but if you accept your misfortune and handle it right, your perceived failure can become a catalyst for profound re-invention.

So, at the age of 47, after 25 years of obsessively pursuing my dream, that dream changed. For decades, in show business, the ultimate goal of every comedian was to host The Tonight Show. It was the Holy Grail, and like many people I thought that achieving that goal would define me as successful. But that is not true.

No specific job or career goal defines me, and it should not define you. In 2000 — in 2000, I told graduates to not be afraid to fail, and I still believe that.

But today I tell you that whether you fear it or not, disappointment will come. The beauty is that through disappointment you can gain clarity, and with clarity comes conviction and true originality.
Many of you here today are getting your diploma at this Ivy League school because you have committed yourself to a dream and worked hard to achieve it. And there is no greater cliché in a commencement address than “follow your dream.” Well I am here to tell you that whatever you think your dream is now, it will probably change. And that’s okay.

It's definitely a beautiful way of looking at failure. The road to success will always be paved with disappointments. That's a fact of life that we all have to come to terms with. But real success isn't solely measured by your ability to reach the top. It's also about the kind of person you've become while you were at it. Did you take advantage of someone else? Did you steal? Did you cause pain? I guess, my biggest take away from this book is that when things like this happen, there are no clear winners. On paper, there might be. But victory lies with whoever walked away with grace, humility, and compassion. So, with every triumph, we must never forget to ask: "At what cost?"

Forever echoing my favorite sign off from Conan:

Work hard, be kind, and amazing things will happen.

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