Is there a quick way to sum it up? NBC, wanting to avoid the mistakes it had made at the end of Johnny Carson's run on The Tonight Show -- where Jay Leno's manager Helen Kushnick conspired to force Carson out, Carson went "forget this, I'm leaving under my own power," NBC brass wrangled awkwardly over whether the host job should go to Leno or David Letterman, then panicked when Letterman got a legitimate offer to move to CBS so NBC seriously attempted at the 11th hour to give Tonight to Letterman but under surprising and maddening terms that made Letterman go "forget this, I'm leaving under my own power" -- attempted to set up a legitimate line of succession for Tonight so that Leno would pass the baton to Late Night host Conan O'Brien in 2009. And made a whole bunch of new mistakes, pissing off both Leno and O'Brien, and in attempting to please both the hosts and the network affiliates wound up pleasing no one with Leno's misbegotten 10:00 p.m. nightly show. That thing ran from fall 2009 to January 2010; the network had hoped it would run for years.
In the aftermath, Conan was gone from the show he'd dreamed for years that he'd host (ultimately, he hosted The Tonight Show for seven months) and was doing the talk-and-be-funny thing on basic cable's TBS, Leno was reinstalled at Tonight, and NBC's ratings were in the toilet. Meanwhile, Letterman was licking self-inflicted wounds due to his affairs finally going public, Leno had become almost-friends with future competitor Jimmy Kimmel (and whether or not Kimmel's BRUTAL Leno impersonation nixed that is something I'm still unsure about -- hard to tell what Leno really feels about stuff), newer late-night hosts Jon Stewart, Stephen Colbert, Craig Ferguson, and Jimmy Fallon were doing what they could to make their names...and, overall, everyone's late night ratings were down. It was complicated, but in the end no one was really happy and they're all still recovering. To the point that many pundits who follow TV wonder if late-night talk shows will ever be a true pop-cultural force again. Is the 21st-century Tonight Show likely to make or break careers the way the show did last century? The jury's still out.
I legitimately thought back in 2004, when NBC made and announced the "line of succession" plan, that Leno was mostly OK with retiring from TV so that Conan could be the new Tonight Show host. Silly me: Leno hated the idea from jump but put on the public face that NBC desperately needed him to have, but that public face slipped away as the change came closer. The 10:00 p.m. plan -- considered not just once, but twice, for Letterman* -- was one of a few not-great options NBC then had, and frankly (the book says) the network likely micromanaged the show into not being able to work at all**.
The book isn't as elegant as Carter's earlier book The Late Shift: Lettermnan, Leno and the Network Battle for the Night (which I re-read last summer), partly because this time isn't as elegant a story that Carter's reporting. It's a mess, with a much larger cast of characters this time, with all those hosts and TV show writing-producing teams trying to make a mark. (That included George Lopez. I'd completely forgotten about his show, but of course it's been years since I've had TBS.)
And all of this wrangling, drama and anxiety over people getting paid very, very well to be funny -- day in and day out for years. Comedy's always been neurotic; using national television to make millions of people laugh -- such a subjective reaction, finding something funny -- raises the stakes to ridiculous, crazy-making levels. Be funny, but consistently funny; have a style that will attract enough millions of viewers to make the show profitable; be surprising but not too surprising (you want people to be able to follow your humor); possibly stretch boundaries of taste if you can be funny doing it, but don't break those boundaries too outrageously or you may just offend; DON'T OFFEND FOR THE SAKE OF OFFENDING (okay, that's more a plea from me, as I get tired of it); conversely, keep safe enough that you don't repel too many viewers; don't incur the wrath of censors, which TV still has; and, if possible, say things substantial and worth saying.*** Think of the genuine political points The Daily Show and The Colbert Report make with surprising consistency.
And you have, to, keep, doing it. Letterman's hosted TV shows almost as long as Carson did. Conan's written for TV since the 1980s and has been on camera for 20 years. Saturday Night Live, one of NBC's current ratings bright spots, has been doing 90 minutes of comedy a week, each season, for 38 years. That last half-hour each week is often a dumping ground for half-baked comedy, but it's tradition for SNL to be 90 minutes; that's unlikely to change. Now I'm thinking about I'd go in and out of the habit of watching certain hosts; I was only ever a semi-regular viewer of Late Night with David Letterman in the '80s, thanks to taping it. I'd take breaks. Likely I needed breaks. Vary the comedy diet. But the sources are consistently there...until they get canceled.
I'm surprised there isn't more burnout among comedy show hosts. People so rarely quit these gigs. That Conan ultimately was willing to quit The Tonight Show -- quit his true dream job, without any guarantee that he'd get another job anywhere near comparable -- seems more impressive now that I've read this book. (I definitely felt more for Conan after this book; he comes off as a deeply decent person. I mentioned to a Twitter acquaintance who's happily met Conan that she should read The War For Late Night: "You might like it. And [you] will love Conan O'Brien even more.")
I don't know any national broadcasters, but in thinking about late-night comedy I find myself respecting even more the people I know who are working to be funny on Internet podcasts...and wonder how they do it, so consistently. And how they support themselves. They're usually barely getting paid or not getting paid at all, because earning money with internet content remains such a crapshoot. The stakes are lower, as are the audiences -- audiences of hundreds, thousands, or tens of thousands don't have the same (at least perceived) demands as audiences of millions, the audience size that TV often needs -- but the neurosis of humor is still there. Must be funny, must be funny...
I've never been paid to be funny. And I'm not arrogant enough to think I'd be good at that job. That's a good, needed arrogance; we need at least some people to have it. To be good at making others laugh and think, and to know they're good at it. Which will help them through the pitfalls, insecurity and neuroses that come as they do their best to make more and more people laugh.
Me, I use humor as a seasoning for life. So do many of us. But after The Late Shift and The War For Late Night, I admire and appreciate those who have to make daily or weekly meals out of it.
* Circa 2002, The Late Night War reports, NBC toyed with wooing Letterman back from CBS and into prime time. But Letterman was just as uninterested in regular prime time work then as he'd been before.
** And whether Leno was suited for it, or could've learned to be comfortable in the different format which required even more prepared comedy per episode than Tonight, is an open question. By the way, this feels to me like a telling moment from the first week of The Jay Leno Show: Jay talked to one of his assistants on-camera, asking him how he'd wound up with the job. The assistant began "Well, it's a funny story..." and started to tell it. Leno then said, "You know, that wasn't actually funny."
*** That was one of my big beefs with Bill Maher's Politically Incorrect. (The other big beef was Bill Maher. Yes, I'm a liberal who can't stand Maher.) It made a show of being about Big Issues And Arguments, but it was too easy for guests and Maher to go the one-liner route and cut off what could have possibly been a thoughtful point. Which inspired me to write this.