Deon Cole gives audiences a glimpse into what it takes to create material for a comedy special — even when the jokes don't work

CHICAGO — Comedians will spend months in comedy clubs trying out new material to see what works and what flops. The good stuff stays. The rest is usually discarded and never seen by a wider audience. But what if a comedian let you see that process?

Late last fall, Deon Cole

“For every 15 jokes I write, only one works,” Cole says in the non-special, called “Workin’ It Out.”

It’s available for free

I caught up with Cole, the South Side native who also co-stars on “Black-ish” and “Grown-ish,”

Q: Walk me through the basics of what we’re seeing here: How do you start to build a show?

A: You start from scratch. You write down a couple premises. You observe different things going on around you and write that down. You might have an old joke that didn’t work before that you might want to bring back out to see if you can find a new way into it. And then you go into the club and see what works and what doesn’t.

So I was at the Hollywood Improv every Sunday night from November to February, until I was about to tour. Every Sunday I was there, in front of 40 people, and would just work on material for an hour to an hour-and-forty-minutes each time.

Q: What’s it like going on stage knowing for a fact that a certain percentage of your material is not going to work? Is that daunting or do you like the challenge?

A: No, it’s nerve wracking! I’m just as embarrassed as you would be trying this for the first time. But it’s the process. That’s the job. You have to bomb in order to rip.

Every time I go work out material, I bomb more than I do good. So I’m showing you all the nights that it doesn’t work. And I have to go through that process in order to chip away at it. One night I’ll go, “Oh this is funny and I’ll keep that,” and it might only be three minutes out of an hourlong set. I’ll go the next week and get another five minutes that work. And it keeps adding up until I have an hour that I’m ready to tour with and then tape a special.

Q: How did this end up on Netflix’s YouTube channel?

A: Netflix asked me about using a clip I had posted online and I was like, “Sure, you guys can use it, I’m doing nothing with it anyway.” And then I started thinking, what other stuff do I have that I just haven’t done anything with?

So I went and looked at all this stuff I shot when I was preparing to tour. And I thought, I have my set ready for the tour, I don’t want to give away that material. But I have all this other material that I should package up and give it to the people because it’s still funny. And I can also give you some insights into how it goes, as far as putting a special together. When you watch a comedy special, you see the glitz and glamour. But what you don’t see is when it doesn’t work and I’m getting heckled and all of that. So I was like, yeah, let me do that!

So I called up Netflix and told them about it and they were like, “Hell, yeah.” And I said, “Let’s not do it on the streaming site, let’s keep it light and put it on YouTube and see what happens” because I didn’t want people going into it like, “Check out this comedy special,” I wanted people to understand what they were watching — and they actually did. And man, a week after it went up I think it had 420,000 views.

Q: One night you’re wearing a wool beanie and sweater with black-and-white horizontal stripes. I’m wondering if anyone’s mentioned that you sort of look like …

A: … I already know where you’re going with that! All of my DM’s have been like, “Where’s Waldo?” I get it all day! The hat was in my car and it got chilly outside that night, so I was like, man, I don’t have a jacket, let me put this hat on. I didn’t even realize I looked like “Where’s Waldo” until after this went up on YouTube.

Q: You also talk about your beef with Stevie Wonder

A: True story. This happened maybe 10 years ago and I would tell people this story — not even on stage, I would just tell people this story. So when I was working on stuff at the Improv, my friend was like, “You gotta try to work on that Stevie Wonder story.” So I did it and it’s funny but I didn’t put in my repertoire to tour with. People have really loved it, I should have kept it!

The woman from the story who was my date, she saw that part. I hadn’t heard from her in years and she reached out to me and she actually texted — and I’m quoting — “I did not know you were going to tell the whole story!” I mean, you did this to me though! You know what I mean? You gave me $100 to leave, what’d you think I was going to do? I’m going to talk about it!

Q: Have you been performing standup at all during the pandemic?

A: I have not. I have not performed anywhere, I’ve just been filming a lot. This is the longest I’ve gone not performing standup and I’m actually terrified (laughs). I know I have to go back. But I’m terrified.

I’m definitely not going to no clubs, that doesn’t feel safe. But they’ve been having stuff in parking lots and outside and those are places I could go. And they’ve been asking me. But I’ve just been like, nah. I just don’t want to do it halfway; I’m not going to feel the energy that I think I really want to feel. So I’d rather just wait.

Q: What is it like to film “Black-ish” these days?

A: Our days are longer, definitely. It takes longer for us to shoot because they have to sanitize each time we come in a room and then go out. Or they have to sanitize every time they move a camera around. They have to sanitize our wardrobe; we have to put our clothes in a special bag before they can wash them. Our makeup takes longer and we all have to be in different cubicles to get our makeup done; and you can only get it done once, so you can’t just be walking around getting touch-ups all the time.

You’re wearing a mask all the time except when you’re shooting a scene. And when they call cut, we put our PPE back on. We’re tested everyday. Even when we don’t film we have to be tested. I’m not filming tomorrow but I have to be there in the morning to go test.

I’m glad to be working. But man, it’s so high risk and so different. But as long as everybody stays on their game — which they have been — and stays responsible, we’re going to be good.

Deon Cole’s “Workin’ It Out” is available on the Netflix Is a Joke YouTube channel.

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