Sherri Shepherd is a dynamic multi-hyphenate. She is a comedian, an actress, a talk show host and most importantly a mother. The Chicago native has navigated the waters of comedy as a Black woman with many challenges and has achieved much success. Rolling out spoke with Shepherd about her comedic journey, the What’s Funny Comedy Festival and dreaming big.
How do you think the What’s Funny Comedy Festival will contribute to the city’s rich history of comedy and support local talent?
You know, it’s so funny because there’s so much funny that comes out of Chicago. Throughout my time in Hollywood. I have met so many comics from Chicago. … I’m just so proud of my friend Lil Rel Howery, for just saying, you know, we have to do something. We have to acknowledge that this city contributes so much to who we are and where we are, our work ethic, our family ethic, and I just love that he is doing that. He asked me, but I was gonna ask him because he was telling me about it, and I was so glad that he asked me because I was gonna beg him to be a part of it.
What impact do you think a festival like this will have on the careers of Black comedians looking to make a name for themselves in an industry that’s so competitive?
I think this is so great, because, Rel is curating such a large crowd and different people, and because he’s got such a great name in the industry, a respected name in the industry people are going to come out that maybe would not have come out because they may not have recognized the names he’s bringing out.
This is his first year doing it, it’s always hard when it’s the first time. That’s why I really wanted to be a part of it, to use my name to help it out. I think that when people see my name, it’ll be easier the next time around. This is how we get back and use our platform. I’m going to be talking about it on my show. So as soon as we get back on the air, I am certainly going to talk about it, and if there’s any comics that I saw or stand out, I’m going give them a shout out.
What do you think is the most important quality for a comedian to have when performing at a festival like the What’s Funny Comedy Festival?
I just think it’s just being able to get on the stage. You have to be authentic.You have to do things that are personal to you. Those are the things that people can’t steal.
What can we expect from this new season of “The Sherri Shepherd Show”?
I’m very excited about the guests that we have and I will tell you this: I went on a private island for eight days, and I just rested. I did a lot of meditating, and I came back with “I got to dream bigger.” I was on a private island owned by a Black man who dreamed big to have this island, and I said, “I gotta dream bigger, and it’s not too late to dream bigger.” So when I was talking to my staff, I said, “I need whatever you’re dreaming about, I need it to be bigger and I need us to resonate with the audience that we see you, that we challenge you to dream bigger.” So I know that on my show I’m going to be taking on challenges that scare me because I want to show people you can do it. It’s not too late.”
The What’s Funny Comedy Festival in Chicago from Sept. 16-22. Sherri Shepherd’s show will take place Sept. 21, 2024, at The DuSable Museum. Buy tickets here.
