
Shay Webbie, fledging funny lady, has hit the ground running, earning a solid reputation in Twin Cities comedy.
Her uproarious stylings get the unabashed seal of approval from the area’s dean of the club scene Fancy Ray McCloney. “Shay is intensely funny,” said McCloney. “This game is all about the work ethic. I see her diligently hitting stages, creating material. The sky is her limit.”
Veteran cutup K Jay the Comedian reflected, “She brings a rare level of enthusiasm and has passion for stand up. I can see her figuring it out at a lot of different open mics, working on material.”
It started with a nudge from Webbie’s homegirl. “My friend Alena,” she recalled, “had told me for years that I’m funny. So, I signed up for a competition I didn’t get into, but, I wound up doing a lot of open mics at House of Comedy in June of last year and from there fell in love.” She loves the craft as much for its therapeutic release as for the desire to entertain.
“I was able to [express] what I was going through and turn it into humor, make people laugh. I tell people, ‘I’m glad you laugh at it, but, it’s more of a release from what I’m going through on a particular day. I’m happy that you can relate.’
“I ran into another comedian who recognized me. He said, ‘I’ve heard so much about you.’ Then, he called me rookie of the year. I was like, ‘Why?’ He said, ‘In the amount of time you’ve been doing comedy, you’re moving so quickly. What it took others three and four years to do, you’re doing it like that.’”
Sure enough, after roughly 14 months, she’s opened for Kelly Kills, Adrian Washington, Kenny Howell and a few others who while not household names are steady headliners.

This August, after being invited to play The Red Carpet in St. Cloud, she was hit with a realization and reflected on how ironic the demographics of her trade can be. “It was between 275 and 300 white people and they loved me. The support was amazing. I was nervous at first and told them, ‘I don’t know if this is a Donald Trump rally and I’m Condoleezza Rice.’ They ate it up. It was dope.”
She’s also been well-received at House of Comedy and Baddies and would love to enjoy that sort of reception in the metro area, where she’s a regular at The Red Sea. “I guess there’s a war going on between Popeye’s Kitchen and Chick-fil-A. Black people can get on Google, Facebook re-sharing, race around to see which place has the better chicken sandwich, but what they’re paying for that they can’t take and support Black talent.
“To come and have a good time. Or just watch [an Internet] video clip and ‘like’ or comment. We don’t support each other like we should,” said Webbie. Nonetheless, currently competing for the prestigious title of Funniest Person in Minnesota, she’s made it to the semi-finals.
Among her influences, Webbie points to Whoopi Goldberg “for so many different reasons, but I’ve always found her funny.” It harks to her teen years as a film extra in her native Oakland, where she worked in movies with stars like Sandra Bullock, Goldberg and Ted Danson. “I was going to audition for Sister Act 2 but got in trouble with my granny. Tracey Ashley is also amazing. I love Tiffany Haddish. I saw a Netflix special and she talks about being a foster kid and living out her car. I grew up in that same kind of environment.”
Following the example, she has turned her troubles into triumph. “It saved me from things like depression, anxiety and suicide.” She added, tongue-in-cheek, “And homicide.” Not all of her drive is about dodging desperation. “Growing up as a product of the system I never had a sense of home until my children, 16-year-old Lyana and 14-year-old Antonio, entered my world [and] taught me to push through, never give up!”
Webbie came by her present, steady gig alongside what could hardly be considered advisable means. She was in the Red Sea audience, basically being a pain to performers. “I’ve always been a smart mouth, that class clown. I was heckling from the sideline and afterward, got added to the show. “So, now, I work each week with Sterling Brown, Jay Boog and Enonesence. They consider me the first woman of the crew. It looks good on my resume that I’ve got a place I’m at every week.”
It won’t hurt, either, in establishing her as a rising star.
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