Updated: Oct 24, 2019
To be honest, it's probably a few thousand. That's the process of developing comedy material. In order to grow you need to try new material in front of a live audience. And most times the new material DOES NOT WORK. At least not in the way or to the level you want it to. Trying new material is scary for everyone. I've seen many successful, even famous comedians nervously reviewing new material before a show. Even asking me or someone else backstage, "Hey is this funny?", or "Is it funnier like this or like this?" - looking for reassurance from just about anyone before trying it in front of a live audience.
You try and give your new material the very best chance to succeed. You surround it with strong bits, because it's easier to keep the laughs rolling than starting from zero. And you deliver it with as much confidence as you can. But very often it just doesn't land. Nobody wants to tell a joke and hear silence in return. It's painful. There's a reason why stand up comedians use terms like, "killed", "destroyed", "bombed", and "died". That's what it feels like. I think many of the most successful comedians are also the most fearless - they kind of have to be.
Jerry Seinfeld's documentary, "Comedian" follows the star on his journey to build a brand new hour plus comedy set from scratch. His first few times on stage, Seinfeld - one of the most famous comedians in the world, attempts five minutes of new material and struggles. Some might say he bombs. It's uncomfortable to watch. When Seinfeld was asked about it later, he dismisses it saying, "It wasn't bad."
When I attended Mike Birbiglia's "Working it Out" tour he spent the first ten minutes reading from a notebook, getting very few laughs from the crowd of 500. It was uncomfortable. A heckler yelled out, "Why are you reading your jokes?". Birbiglia could not have been more calm. He explained: "This is how comedians develop new material. I literally wrote this today and the tour is called “Working it Out." " He went on to explain that it will probably take him four years of working it out until he's ready to record his next special. By the way, much of his hour long set was already very strong but he knew it would take a few more years to get it just how he wanted.
Comedian Neil Brennan (co-creator of "Chappelle's Show") puts it this way, "The most successful comedians are the ones that write the most failed jokes."
It's true. You can't have a lot of great jokes without writing a lot of failed jokes.
Your favorite comedian's Netflix special took a lot of work. It also took a lot of failure.
So, if you want to succeed - find a way to fail more.