Comedian Damon Williams Stands Up for Hometown of Chicago

Damon Williams has worked at City Hall, Subway and – for the last 27 years – has been a very busy stand-up comic.

On Friday, Williams performs at a benefit for Teamwork Englewood at the Kennedy-King College Auditorium.

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He joins us in discussion.

Below, a Q&A with the comedian.

Tell us about yourself. Who is Damon Williams?

I’m a very active, stand-up traveling comedian. I tour basically 50 weeks a year including the U.S., Canada, Caribbean. I’m part of the “Tom Joyner Morning Show” which is nationally syndicated, and I’ve been doing stand-up in Chicago for 27 years. I do a feature on Tuesdays [on the Joyner show], but Friday is Damon Williams Friday. I’m a regular on the broadcast. He rotates three or four comedians per week. We all have a day. Which is really a career highlight because I grew up listening to Tom Joyner.

What are some other highlights from your years in comedy?

One of the ultimate highlights was touring with the “Kings of Comedy.” I did 30 dates including two shows at the United Center, so to go around the country with the four of them and then triumphantly return home to the house that Michael built – I’m an avid Bulls fan so that was pretty awesome. The tour also played the hall, not the theater, at Madison Square Garden, so I’ve stood on stage at Madison Square Garden.

Where do you perform locally, and are hometown shows different?

I’m a co-partner with Riddles Comedy Club in Alsip, so that’s predominantly where I work when I’m home. I’m the promoter-slash-booker, basically a partner. But a show like with Teamwork Englewood where I’ll be right in the community, it does have a more personalized feel due to the fact that my references can be local.

And did you know about Teamwork Englewood?

They reached out to me, but after meeting them and hearing their passion and what their initiatives are, I was blown away.

You’re from Chicago, and still live here, correct?

Well I live in the south suburbs now, but I grew up between Woodlawn and Beverly. Attended Lindblom High School in Chicago. They have an active alumni chapter and they do a lot community-wise.

Is it true you owned a Subway store?

Yes, from 1990 to ‘92 in downtown Chicago. It was one of the first Subways in the Midwest, surely I was the youngest franchisee at 25 and the only African American at the time in the Chicago area. I draw on that sometimes [in my stand-up act], depends on the setting, but when I’m doing more of an autobiographical set, those stories come up.

Growing up, were you the class clown, or the shy kid who blossomed later?

More the latter. I was a middle child growing up, and I didn’t really seek to stand out or be the center of attention, especially when it came to trying to make people laugh. That kind of happened later in life when I was working at City Hall. I worked at City Hall from age 18 as a temp, and then I got a permanent position at age 20 and worked there from 20 to 25. I worked in the Purchasing Department, which they now call Procurement. We started out as data entry operator, going back to keypunch cards, until they modernized and brought in computers, so I was there when automation took place in City Hall during the Harold Washington administration. It was cool to see him coming in and out of the building and just as a young person getting my feet wet with the local political landscape, and working with the local campaign office to try to get Harold Washington elected. That was a real momentous occasion.

What’s next for you?

There’s a new streaming network that’s airing in February and it’s called “Urban Flicks.” They’ve greenlit and budgeted a show for me to do here in Chicago and at Riddles in Alsip. It’s a stand-up comedy show plus an interview segment so most of the times you see a comedy show on Comedy Central or HBO the host comes out, there’s three comedians, they do their set and the show goes off. What we’re going to do is, I’m going to do an interview with each comedian prior to the set, and then they’re going to walk to the club and do their set. We’re doing 12 episodes and we’re shooting Oct. 29 through 31 at Riddles. And the name of the show is “Laughs Tonight with Damon Williams.” Also I’m a recurring contributor to “Windy City Live.”

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