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Will Miles was one of the funniest stand ups in Chicago. Now he’s one of the hosts of the most buzzed about weekly show in Brooklyn, Comedy Night at the Knitting Factory. He’ll be at the Black Cat this Saturday with Giulia Rozzi. -ed.

I love doing comedy. When a show is great, a comedian holds onto that feeling of having a great show for almost 24 hours. When a show is bad, a comedian never forgets that show for the rest of his/her life. One example of a bad show is the time I did a show in a casino room where the only audience was my friends family, my family, and two men in a conversation in the corner smoking cigars while blowing the most smoke humanly possible directly toward the stage. At another show, I was told, “Alright you’re next” right before I watched an audience member throw a chair onstage at my friend, beginning an entire bar brawl. Less than one minute after the chairs were picked up and certain audience members were escorted out, I heard, “Your next comedian coming to the stage….Will Miles!” Those could be considered “nightmares,” but none as much of a personal nightmare as a show I did in Chicago. It was maybe my fifth time onstage doing stand up comedy. Ever.

The stage was set. I had done a few shows to varying amounts of success for a beginner. My first comedy show was a competition that I won because I brought most of the audience. My second show I came in third place because other people brought audience, but I still brought a lot of them. My third show was in front of mostly friends at what would become the place I performed the most, Town Hall Pub in Chicago. My fourth was at a small show put on by some people who saw me at my third show. And that set went on YouTube, so I felt like I was ready for anything. In my head, once you were on YouTube, you were a famous comedian and deserved money at clubs and colleges all over the country. I was stupid and wrong. My fifth show is how I found out I was stupid and wrong. My fifth show was a fundraiser that a friend of my fathers was putting together. I figured it would just be a regular show in front of some people who wanted to see comedy, and that much like the other shows, it would be easy and pressure free. Then I got an email telling me that they would be on the radio promoting the show.

“A little higher stakes than I had planned, but based on my previous four comedy shows, I should be fine..” I thought immaturely.

When I got to the venue, my picture was on flyers all around the theatre, right next to comedians who all had television credits and had been doing it for at least ten years.

“Shit. I will not be fine,” I thought. “I’m in way over my head.”

I was definitely in way over my head. To add to my anxiety, another acquaintance of my father was in the audience. Only he happened to be legendary filmmaker and comedian Robert Townsend, who hadn’t seen me since he almost cast me in Meteor Man 15 years before. He didn’t cast me in Meteor Man because I got too shy when he and the crew said all I really had to do was show them a dance and say a line in order to be in the movie. I watched as my father told him about my new life 15 years later, my new career ambitions, and my commitment to the craft and the art of stand up comedy. I watched him say these nice things, and the whole time I watched, I knew I was about to bomb horribly. And I repeat….horribly.

So I hit the stage. My first line was “How are you guys doing tonight?” and by the time I said “tonight” I was in the middle of a full panic attack. Sweat was dripping inside and outside of my shirt. I continued to bomb. I sat in my bomb and got used to it. I got to know my bomb. We became good friends. I left the stage. The host, as hosts often do, came back out and commented on the bomb. He brought an urn with him, and said the line, “This urn is for that last comedian who just died up here.” I bombed in front of my largest crowd yet. I bombed in front of my proud parents. I bombed in front of their friends. I bombed in front of their famous friends. That set will haunt me forever, reminding me that no matter what I do, I will always have that bomb that day in front of all of those people. It also reminds me that I have really dope parents. They just acknowledged my bomb, supported my career, and dropped me off at the next show that night. I owe my parents and that show for any success I have in this business (but I will not be paying any money back to the bomb).

That night, I lived a nightmare. It wouldn’t be my last nightmare. However, much like the night I lost my virginity, I will never forget those six minutes. Ok…maybe five and a half minutes. Ok…maybe five minutes. For those four and a half minutes onstage that night, I was trying desperately to wake up out of my nightmare show.

Photos by Mindy Tucker, courtesy of Will Miles