I watch a lot of late night television, mainly due to the fact that I work overnights and thus am awake when the shows start at 11:35.

If you’re a connoisseur of the genre and know me at all, it’s probably no surprise I gravitate towards David Letterman and Jimmy Fallon. But for a short time, I at least had to make a choice in that early time slot. That’s when Conan O’Brien hosted the “Tonight Show.”

I just finished reading Bill Carter’s “The War For Late Night” which chronicles the rise and fall of Conan’s “Tonight Show” run, from his initial guarantee to host to the day last year when he accepted a settlement from NBC and took his show to TBS.

I knew all the big-picture stuff about this saga from having watched it play out on TV at the time, and also read about some of the insider stuff as well. It was fascinating to read Carter’s description of how everything was working inside NBC, as well as the Leno and Conan camps, as all the decisions and negotiations were taking place.

If you’re not familiar, here’s a very basic timeline of what happened:

-NBC gave Conan a guarantee that he would host the “Tonight Show” after a set number of years, upon which they told Leno he would be done

-Leno wanted to stay on TV, and combined with NBC’s fear he would bolt to compete with them at say ABC, he ended up with an ill-fated show at 10 p.m. on NBC

-Neither show did great in ratings, and NBC affiliate stations complained their news ratings were being crushed

-NBC reacted by floating a plan to move Leno back to 11:35, and shifting Conan and the “Tonight Show” to 12:05

-Conan balked, the network chose to stay with Leno and pay Conan a multi-million dollar settlement

Throughout the entire process, and especially in the accounts in the book, Conan comes across as sort of the righteous character in the story. He didn’t do everything perfectly, and maybe what NBC was asking wasn’t so bad, but people generally felt Conan was being screwed.

The shame is that in the end Conan is now stuck on TBS while Leno continues to dominate the late night ratings on NBC. Carter talked to many of the other players, who gave really candid assessments of the situation and their colleagues. Many of the major names are Letterman disciples and don’t get Leno’s appeal. Jimmy Kimmel, who hosts a show on ABC at 12:05 describes Leno’s brand of comedy saying, “I think he turned comedy into factory work–and it comes across.”

Sure, there are “Leno people” and everyone is definitely entitled to their opinion about which shows are more entertaining. But I think actor and one-time Conan roommate Jeff Garlin sums up my view pretty well:

“It’s like comparing John Coltrane to Kenny G,” he says in the book. “One of Kenny G’s albums probably sold more than all of John Coltrane’s library. But you can’t tell me for a second that Kenny G is better than John Coltrane.”

While I knew a lot about this set of events, a lot of what I enjoyed about this book was learning more about Conan. I was vaguely aware that he had written for Saturday Night Live and The Simpsons, but even as a total Simpsons nerd I had no idea he wrote the amazing “Marge vs. the Monorail” episode and the one where Homer goes back to college.

But there is also a lot of real insight into Conan’s mind as a creative individual, particularly with the self-doubt that often comes along with the process. Carter describes it as “imposter syndrome” saying that as eager as Conan was to take over the “Tonight Show,” there was always “the thought that, no matter how successful you became, ‘they’re about to catch up to you.'”

I don’t know many creative people who don’t think that way. As much as we are proud of our work and know that some things we do rock, hitting the “publish” button and sending our stuff out into the world can be extremely nerve-wracking. There’s always a sense that it could be better, and that there has to be some kind of luck to people thinking what we are doing is special. I know that when I was in school, no matter how good my grades were I had the feeling that some day, someone was going to figure out I’m really not that smart.

I’ll close with Conan’s closing to his “Tonight Show” run. He spent his final days absolutely lampooning NBC in a string of shows that belongs in some kind of entertainment hall of fame. The process crushed him. NBC was ripping away something he had dreamed of since he was a kid sitting and watching the show with his father. And yet, while his legion of young fans who don’t need much to be pushed into a cynical view of the world rallied behind him, Conan said this:

“Please don’t be cynical. I hate cynicism — it’s my least favorite quality and it doesn’t lead anywhere. Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you’re kind, amazing things will happen.”

Amen.