How to be funny with Charles Duhigg featuring Gary Gulman

by Glenn on August 20, 2019

I came across a podcast called “How to! with Charles Duhigg”. The premise is that someone asks Duhigg how to do something and he finds someone who can explain how to do it.

In the episode titled, “How To Be Funny,” Duhigg wants to help a pastor, Aaron Kirkpatrick, be better at telling jokes. Kirkpatrick wants to use humor to engage his congregation better when he preaches. Duhigg knows that “being funny is really hard to do well” so he goes to a New York comedian, Gary Gulman, for advice. I had never heard of him previously, but he has this really funny comedy routine which he performed on Late Night with Conan O’Brien:

This was a great routine (albeit with an expletive).

The podcast offers some insights. You get a bit of Gulman’s story and Duhigg does a great job narrating. It’s a long path to become a proficient comedian primarily because it’s a hard road to develop material and “to get a new joke to work”. Gulman says that none of the material he used in the early years of his stand-up routines made it into his first television special. He said a great thing about that early material: “It was useless except that it was so useful.” He suggested a metaphor of a musician who has to spend his early years practicing scales.

The thing I enjoyed the most about this podcast, though, was hearing Duhigg analyze the above routine and Gulman explain how he developed it. It took twenty years. Twenty years! Comedy routines need structure and an ending and, in this case, it was difficult to come by. Along the way, Gulman learned that it was okay to lie in the pursuit of comedy—it’s called “artistic license”—and, inspired by the documentary, Helvetica, he created a mythical documentary and dragged in a story from his past about an omelette bar. And now this routine sings, even though Gulman remains critical of it.

The comedian Patton Oswalt was asked if there was a routine that he wishes he could take from another comedian. He referenced this one by Gulman. Someone said that Patton believed doing a routine “on just one idea” was “akin to tightrope-walking without a net.” Patton says:

“Do you know how terrifying that is to risk? As a comedian? If you start down this road and it’s NOT clicking? There’s no ripcord. No bolt-hole to safety. You’ve chosen this track and you better hope it brings you to the next station instead of suddenly ending in warped rails over a crevasse. I’ve only seen a few people pull something like this off. Jake Johannsen did a spot on Letterman back in the 90s where all he talked about was the Midwest kid who got his arms torn off by a thresher and called 9-11 with his nose and teeth. That was the whole routine. And it destroyed.”

The problem for pastors and humor is two-fold: you need new material every week and you are a truth-teller. You’re not developing a routine to take on the road and do over and over. If you tell a story, you have to wait a long time before you can tell it again. And while truth is not that important in comedy, you need to be careful to separate truth from fiction. It’s no problem if people find you entertaining, but you are not an entertainer.