As 1998 was coming to an end, I was approaching my 30th birthday. I had thought about trying stand-up comedy for many years. Like, 6 years. Never had the courage to try it. Kept putting it on the back burner.
As 1999 was approaching, I made a vow to myself to try it. On Jan. 17, 1999 I signed up for an open mic at @yukyuks at Yonge and Eglinton. It was the first step.
You see, the way it worked was that you called and left your name on a voice message before Monday and then you would call back after 3 pm on Monday to see if you had been chosen to go up that night. About 15 amateurs would get up.
Most were regular amateurs, so I knew I would have to call back for many more weeks until they started to see the regularity of my calls. At least that what I was told. So, it bought me time. The call was made, I had weeks to prepare for my 5 minute set. And weeks to back out.
WELL, a friend who I was waitering with at @TheKeg had been doing a few amateur nights for weeks weeks so when he called to see if he got up, and heard my name was on the list. WHAT! This meant I now had my 5 hours to prepare these “jokes” I’d been scribbling on paper for 6 yrs
There was no way I was going to do it but that friend encouraged me to go. Without that push, I bail for sure. You see, it’s one thing to think you are funny or be told by your friends you are funny, but the thought of doing it in 5 hours at a comedy club was terrifying.
I knew if I didn’t go this time I’d never do it. So, I went. Told two friends and nobody else. Not my family, not my teacher friends, nobody. I was always comfortable speaking in front of people. School speeches and presentations were my forte.
However, when I walked into that club I was terrified. TERRIFIED. It’s a feeling I had never experienced before. But again, I knew I had one chance at this. After all, I was 30 years old. Most of the other comics were mid twenties and some had been doing this for 5 yrs already.
I walked over to the list and saw my name on the list. 13 th out of 17. Not my full name, of course, because I wanted nobody to know I was doing this. You’d think I was stripping but it was just stand up comedy and I was afraid anyone would find out.
So, I went with “Gerry D.” Stevie B. was big at the time and it worked for him. Dumb. As I paced back and forth at the back of the room convincing myself I could do this, another comic would go up on stage. My turn was coming up. Thought about leaving about 25 times.
But, again, I was so close and knew this was it. I knew I would never try this again. Then my name was called. The MC made fun of the “Gerry D.” name. The first laugh. At my expense. Not off to great start. So nervous. Go on stage. Didn’t say hi. Just started my set. My awful set
I bombed. Badly. It was like talking to a wall. 5 mins felt like 50. Beads of sweat rolling down my face. Was supposed to end on a big Lionel Ritchie, “Say You, Say Me” bit, but they couldn’t play it because someone was in the office. Then a voice of God told me my time was up.
I was embarrassed but also a bit relieved. As I was walking off stage, I heard a comic yell, “stick to teaching”. I know who it was. We spoke about it years later. I will never forget that. “Stick. To. Teaching”. It bothered me that I bombed but that bothered me more.
I knew I could do this. I knew I could. I could easily have listened to him and never done it again but I knew I just needed time to figure it out. Funny is funny. I just needed to figure it out. So, I kept signing up. Kept bombing and kept getting on stage as much as I could.
I started to get laughs here and there and there was no feeling like it. And slowly, but surely, I started to figure some things out. As, “Gerry Dee” now.

I tell you all this story In case there is something you have always thought about doing as we enter a new year.
I was so close to never pursuing this career. So close. I’m so glad I did. I can tell you it took a lot of hard work as well as some lucky breaks but most of all it came from never wanting to fail again like I did that first night. I also knew I could do it.
Happy New Year everyone. May you try something new, chase dreams and work towards new goals. You never know where it will lead you. Take it from me, it can lead to some wonderful things but taking that first step is always the hardest. So start walking...good luck.
You can follow @gerrydee.
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