I’ve had a lot of fun writing the first two stories in this series. They’ve been fun for a lot of reasons: it’s been great to reminisce about the old days with some of my friends who have read this, I hope I’m presenting some good lessons on what not to do to newer comedians, and it’s been a super-joy to dunk on some assclowns who kinda (absolutely) deserve it.
To start this newest edition, however, I think I’m going to start with the best piece of advice I can give anyone in comedy when dealing with a booker. Not only is it good comedy advice, but it’s good life advice.
Be honest and self-aware.
I know this seems like obvious advice, but the amount of times I see booking emails with outright lies in them has been too many to count for a number of lifetimes. Honesty is not that hard.
If a booker asks you how much time you’ve done, they don’t mean for you to take a guess at the amount of time you could do if you put every joke you’ve ever done together. They want to know what is the longest time you’ve ever done. If that’s five minutes, just say five minutes. We love honesty and might just ask you to come do your five minutes for us!
One of my favorite exchanges with a comedian ever comes from suburban comedian and producer Alex Krochman (whose stage name was Crockman, but I don’t feel like I’m giving away a trade secret). Alex had done a few ten-minute guest sets for my show, and had crushed them. I was a fan and asked Alex when he would want to come and perform twenty minutes for me. I knew he would be thrilled to do so, and I was excited to see it. I still remember what Alex said.
“I’ve never done twenty minutes before, and wouldn’t be comfortable doing that here. Can I let you know when I’m ready?”
I wanted to kiss him on the lips.
Here was a comedian who trusted the relationship he had with me so much that he was willing to turn down time he didn’t feel ready for. At that moment, I knew that I would try and help out Alex however I could. People like him are one in a million.
So, that takes us to today’s story. Unlike my experience with Alex, this goes the other way…
We return to 2010 to the first show I ever produced, at the Clearwater Theater in West Dundee. Man, did I have fun running that show. And man, did we only get an audience, like, three times.
At some point in booking this show, i got a message on MySpace from Tim. Now, Tim is not this man’s real name. Or maybe it is. Honestly, I don’t remember. You’ll see why soon enough.
Tim’s message was everything I like seeing as a booker. It was polite and succinct. Tim told me that he used to do stand-up comedy all of the time in college but hasn’t done it in a little bit and was hoping I would put him onstage for five minutes. Honestly, as a producer, it’s kind of a win-win scenario to get a message like this. If the set goes great, you’ve established a good relationship with a comic you enjoy and that’s something that can build for years. And it the set is a bust? Oh well, it’s only five minutes. No harm and no foul.
A date was set and I was excited to see how Tim would do.
It’s a set I would never forget.
Before we continue, here’s something you should know about the Clearwater.
I tried to find a good google image of the inside of the theater, but struck out, so I’ll try and describe it as best as I can.
I would watch shows from the very back of the theater, where people would enter. Once people came in, they would go down some steps and get to some tables and watch shows on the stage, which was about five feet up in the air. It felt like the comics were towering over the audience and I always hated that.
To get to the stage, I would walk up the side entrance to get to a door where I would wait in the wings until it was my time to go on. From the back of the room to that stage entrance door was about 40 yards or so. The theater was way to big for me to be running a room in, but I didn’t know any better.
Had I even a little more producing experience, I probably would have been able to guess what would happen.
It’s the night of Tim’s show, and he shows up early and is super-excited. He knows that I’m going to host the show, which means I’ll do about ten minutes and then introduce Tim. We’re waiting in the wing and right before I’m about to step onstage, he puts his hand on my shoulder to stop me.
“I’m so sorry,” Tim says. I’m able to see what’s coming now, basically because he looks so nervous.
“I’ve never gone onstage before. I just told you I had because I didn’t think you would let me go onstage unless I lied.”
Keep in mind, at this point the show should have started.
I’m not sure if Tim was telling me this because he wanted to come clean. There is part of me, in hindsight, that thinks he was hoping that I would be so mad at him that I wouldn’t let him get onstage that night.
Instead, I just say, “Well, let’s see how it goes!” and walk onstage to start the show.
I do my time, ask everyone to give a big round of applause for Tim, and then walk offstage where I grab a beer and head to the back of the room to see how he’s doing. Right away, I can tell it’s not going well.
Tim is getting zero laughs. It’s the kind of dead silence where you can feel the judgement of the audience. You can almost hear their inner monologue: “Whoa… is that what this person thinks is funny? Because it is not. I better make sure I make zero noise so this person knows how unfunny they are.”
At some point, Tim tries to start talking in a silly voice. Nothing. Then he starts flop-sweating and talking very fast. The crowd has not made a decibel of sound. He’s been onstage for about seventy seconds.
Then he leaves.
He mumbles something that sounds like, “Thank you,” and makes a beeline offstage. I, the host of the show, now have to sprint from the back of the theater to get back onstage. Because I am not Usain Bolt, it takes a while… longer than I would care to admit.
When someone has done that poorly, you cannot bring the next comedian onstage immediately. You have to try and get the audience engaged again. So, I’m onstage for a few minutes. Because of that, I miss what happens with Tim next.
According to another comic on the show, Tim sprints back to the bathrooms, vomits very loudly, then runs out of the building.
I would never see him again.
The next day, I sent Tim a message. I told him that, as far as first sets went, that was nowhere near the worst I’ve ever seen.
I’m not lying.
I also said that comedy is something that takes work and dedication and, if he ever wanted to try again, I would happily go to a couple of open mics with him.
But Tim never got back to me. I never saw or heard from him again.
I think about Tim sometimes. I hope he’s doing well and is happy. I hope that if he wanted to try comedy again, he found the courage to get up at an open mic and not put that kind of pressure on himself.
And I always remember the lesson it taught me when dealing with comedy producers: Be honest.
Fancy Boys Club 
It is interesting to me to see that many folks who attempt standup don’t understand you have to prepare funny material, practice it, and then have the confidence to execute it. The make up of crowds may differ but if you are any good you can still be interesting if not funny. Some of the comics that I have heard just speak of their miserable lives. While it may be good therapy for them it can be depressing and not entertaining.. I considered trying standup after watching Carrie Fisher”s HBO special. She spoke of her battles with addiction, weight loss, and the time that she woke up in the bed with a dead man. After hearing her sad story, I knew that I could never be less funny than her.
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Interesting post Matt. We (duo) started performing comedy about 5 years ago, it was a charity night and we got dared for a 10 minute open mic set. Around 200 people attended this event in London. We practised the c**p out of our set and on the night, while bricking our pants pulled it off well. But we knew is was a charity event and we were an open mic set, I think everyone was kind on us.
The same year we performed a similar set for another charity night. After that we formed ‘Chucklesinghs’ and have performed and hosted our comedy nights across the UK. Where possible we will see a comedian a few times to get a taster. Only once did we not see a comedian (saw her material online) and it was a tough watch from the side. She was a smart comedian but I had told her the crowd for our night liked slap-stick comedy. Since then we bind our cast carefully to give as much flavour as possible.
We are insistent on two things – how much time and how much. We tell them the max audience size and demographic…then that’s where we expect the honesty part.
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Matt,
I’ve just read four of your pieces and I smiled the whole time. Interestingly, at the close of each one, I found myself wanting a few more paragraphs about what else may have happened, a description of how you felt about it, or what you think about it now. Far from a criticism, you left me wanting more. This is likely why you are a good comedian and I would drive any set into the ground. It was so refreshing to hear your voice in these line and a real pick me up today. Love you and trust you are well.
Brian
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