Go for the killer set or churn out new material?

For a while, I was constantly churning through new material. Why? 1) I get bored doing the same jokes over and over. 2) I didn't like the idea of other comics seeing me do the same joke multiple times. 3) I wanted to do fresh material at each Flying Carpet show (which happened once a month). 4) I figured the best way to learn about creating funny was to try to keep making it from scratch. 5) I was also working on characters like DJ Underground or The White Collar Comedian which would sidetrack me from my "normal" bits.

So I was always writing and trying new stuff, rarely saving a joke for longer than a couple of months. But one night this summer, my attitude changed. I showed up to do a set and it was (surprisingly) a great crowd. And they were filming the whole show too. I got up and was doing really well for the first four minutes. And then I kinda fell apart. Nothing terrible but a chance at a great tape slipped through my hands.

I got offstage and was really pissed off at myself. I decided to take a different approach. So for the past few months I've been working a lot more on honing jokes and trying to wittle my best stuff into a killer 7-10 minute set...even if that means repeating jokes that I've been doing for a while.

In this interview, comic Ophira Eisenberg — I've never seen her but I think this quote is interesting — says you have to work on seven minutes for a year to make it perfect.

I do my material four times and I'm bored with it. But, I've learned that I can't do that. When I was pursuing Premium Blend, I learned you really have to work on seven minutes for a year to make it perfect. You have to be able to say, 'I know how this works and you can count on it.' Then they'll say, 'Of course!' I used to try something new every second day and that was great. But I never honed stuff. Jim MacAleese, a comic from Canada, once told me, 'It's called a routine for a reason.'

I think there are lots of comics who take this approach. I just dislike the idea of intentionally viewing your act as being "routine." That feels overly stiff to me. There's gotta be a middle ground here, right?

Lately, I've been taking a two tier approach. I've got my A material. If there's a decent crowd, I go for it and try to have the set of the night. If there are comics in the back who have heard all those jokes before, oh well.

Then I've got my "undertow." A constantly changing series of bits that I try at open mics or shows with meager audiences. In those places, I often throw in some more personal stuff, talk about the room, etc. Sometimes I intentionally go into stuff that is unformed just to see if I can riff into some gold. (At the very least, this keeps me conversational...which I've found to be the best approach in a dead room.)

Some benefits to going back to the same jokes over and over: You get an air of confidence. When you know a joke works, the audience can sense it. Also, you start seeing ways to stretch jokes. You add in a new tag or figure out a way to fold a good joke into an existing bit. Or you keep going deeper and deeper on a subject (one good technique: keep asking "Why?"). Sometimes it's the 20th time you tell a joke that the perfect callback or end line comes to mind. And thankfully, that one extra line or change of wording can make telling an old bit feel fresh again.