I'm not a big fan of books and classes that purport to teach comedy writing. First off, way too many of them are taught by folks who are trying to make money that way because they can't make it by actually writing comedy. Secondly, there is an aspect of Being Funny that can't be taught, or at least can't be taught to someone who does not already have at least a smidgen of it. And if they do have it, there's an awful lot to say. One of the reasons I stopped teaching Comedy Writing down at U.S.C. was that I felt I couldn't teach enough of substance to my students in two hours a week.
In the past, when people have asked me to recommend a book on the topic, I've balked and said if there is a good one, I haven't seen it. Well, now I've seen a pretty good one, at least about one kind of jokesmithing. It's called Comedy Writing for Late-Night TV and it's an amazingly thorough book on the subject by Joe Toplyn.
This is not me shilling for another of my writer buddies. I don't know Joe beyond a fast handshake and a "nice to meet you" but have heard many good things about him from folks who worked, as he did, over on The Tonight Show with Jay Leno. Joe's first big gig was writing for Letterman, back in what some would describe as Dave's Golden Era. After that, Joe transitioned in and out of sitcoms before returning to late night with Chevy Chase's talk show, a program that could not have been saved by the combined writing prowess of every single Jew who ever worked for Sid Caesar.
After that, Toplyn signed on with Leno…and this was the period when Jay was getting beaten soundly in the ratings by Letterman. From all reports, Joe was a major contributor to the reversal of fortune, especially in increasing the quality and volume of the show's comedy bits apart from the monologue. He writes about that turnaround in the rear of his book and the many pages before discuss the construction of those comedy spots.
What I like about this book is that it doesn't purport to tell you what makes a joke funny. Jokes are like frogs: You can't dissect them without killing them. But there is much to learn about the handling and the organization and the disciplines and most of all, the structure. And if you yearn to write for that kind of TV show, you couldn't find a better book telling you how to go about it. So here's my recommendation and an Amazon link. Use it in good health…and humor.