Catching Up with Comedian Sheryl Underwood

by Andre Ash

Comedian Sheryl Underwood is a legend on the comedy scene. Gracing stages, television screens, and television, the multihyphenate star has tapped into a career of longevity both as a comedian and even a daytime talk show host. She has become a household name in Black America, but her talent and unique ability to create connections with people from all walks of life have made her a cherished figure across a wide range of demographics throughout the country. Michigan Chronicle caught up with the beloved comic during the Cincinnati Music Festival as she weighed in on her time in Detroit, staying healthy and surviving the sometimes-brutal realities of comedy.

Michigan Chronicle: How much love you got for Detroit?

Sheryl Underwood: Detroit is my spot! I used to go to Inkster, a club called the Star Dusk. Best food in the world!

MC: So, have been your favorite hangout spots in Detroit?

SU: Well, I like the after-hours because you really get to talk to both sides of Detroit. You get to talk to the movers, the shakers, the politicians, and the different sides of the world.

MC: Let’s talk about your partnership and collaboration with Metamucil and the Divine Nine (Black Greek Letter Organizations) and your ambition to stay healthy.

Kids go off to college; they’re not eating right, so they need more fiber. So, for me, I think a gummy and you each just three of them, you’ve got the equivalent of two servings of broccoli in your system. For somebody like me to be talking about Metamucil, people have been watching me since Def Comedy Jam, BET Comic View; they know Auntie Sheryl, but I do like more that I have my guy friends and different comedians I know…talking about it, and that’s important to me.

MC: After many years of standup, when you look at the comedy scene today, do you still love it?

SU: I love it dearly. I think comedy is my man – is, will always be, my man, and will never separate. We are on tour now. We started at Johnny T’s Bistro in Jackson, Mississippi, so we will be on tour going into comedy clubs. One thing I like about comedy is that it’s portable, and for most comics, we’re the visionary; we’re the eyes and ears of the street, the movement. When you talk about what Dick Gregory did, he was making $10,000 a week and decided he was going to put his money and his heart into the movement. We can do that again. So now we’ve got the Dave Chappelles, the Chris Rocks, the Kevin Harts, the Steve Harveys, the Sheryl Underwoods, the Moniques …Tiffany Haddish.

The one thing I love about it, too, you can take comedy into any nightclub or comedy club and bring people together. It’s a little dicey right now, but sometimes you have to figure out how do you want to make that joke but also make that point.

When I did Laughapalooza in Atlanta, I was doing a political set in an urban way. I’m coming out back into comedy as old school Sherly Underwood – Def Comedy Jam, BET Comic View, all the language. The Sheryl that everybody grew up with and recognized. As God gives me the message, the things I need to say to touch the hearts that I need to touch. We’ve got to tell people that you’ve got to vote, you’ve got to participate in the growth of your city, you’ve got to participate in the growth of your family, and you’ve to reach out to people that you don’t know so that we can make this country even better than what it was. It’s doing alright, we cool, but it could be much, much better, and sometimes comedians can articulate that in a different way.

MC: As your career trajectory has evolved as a host now on daytime television on CBS ‘The Talk,’ so has society evolved into what is known as cancel culture. Comics also can’t comfortably say the things they once said before to say today. What’s your take on cancel culture?

SU: Well, I had a concern at some point, which is why I haven’t been on the road since COVID. About three or four years and, I just asked GOD to order my steps and asked, ‘is this where I should go? Is there a message I should give?’ I will say this: I was saying wild stuff that parts of my audience didn’t agree with. But as the audience came together, as the audience became more diverse, then people said, ‘wait a minute, I like the jokes.’

When I first got on ‘The Talk’ and my audience demographic started changing, them little white ladies were like, ‘we want to hear Sheryl’, so I was like, ‘OK.’ To me, you take the risk, you try not to disrespect someone. I’ve been in situations where things have happened, but you’ve got to test the joke and let the world see your heart, and if you step in it, ask for forgiveness. Just say, ‘I was wrong.’

I think the only thing that is different is technology. It’s social media. When we were coming up, you didn’t have a gadget, so when we went to the Earth, Wind, and Fire concert, nobody was holding up a gadget. We might’ve been holding up a light, but nobody was holding up a gadget. So that means nobody would’ve seen Usher dancing up on KeKe.

In the same token, you’ve got to use technology for the power of good because it documents things so when someone tries to say it didn’t happen, oh yes, it did.

So, it’s a bittersweet relationship; you have to have it because it is the civil rights movement of this generation. But in comedy, it’s the spoken word, it’s the joke. I would joke that people would understand that the jokes are meant to make you feel good. I’ve been telling diverse jokes for a while, and I like to layer them with getting us to buy stock because you won’t buy stock, but you’ll buy a lottery ticket every Friday.

You have to have courage to do comedy, write the jokes well, and people don’t take it so personally. We live in a country where you have a right to say what you feel, but you also have a responsibility to that response, and it should bring us together.