Portsmouth comedian Cletus Kassady gains popularity with comedy bits on City Council meetings

Portsmouth comedian Nicholas Gordon has spent the past 20 years making a name for himself as Cletus Kassady. He’s performed stand-up, written for others and acted in films across the country — with one set to premiere this fall. He’s opened for comedic stars like D. L. Hughley and Mike Epps.

But since May, Kassady’s been growing his local following by turning Portsmouth City Council meetings into comedy bits that poke fun at council members while offering the news of the day.

And the dysfunctional council is the gift that keeps on giving. After each meeting, Kassady can be found on Facebook Live providing a rundown, peppering his analysis with jokes, barbs — and even nicknames for the council members — to the delight of his audience.

“The jokes write themselves,” he said. “You gotta laugh to keep from crying.”

Kassady, 45, has been performing comedy professionally for 16 years, with the past eight full-time. He performs “clean” comedy, which he defines as family-friendly, age-appropriate humor with no cursing.

As a comedian, Kassady stays up-to-date with current events and politics to remain relevant, especially at the local level. A resident of Portsmouth’s Cavalier Manor neighborhood, he’s been following the City Council’s dealings for years — sometimes in person, sometimes by watching the video recordings.

And he said the May 24 council meeting, where a majority of the council voted to terminate City Manager Angel Jones, left him “in pure shock and awe.”

He posted his first recap on Facebook Live later that night. To his surprise, it was so well-received that he committed to posting after each meeting.

“When I did that recap, it was amazing to me the number of people who reached back out to me and they were like, ‘Thank you, ‘cause you gave it to us in a way that’s palatable. You gave us information that we didn’t even know and we can now understand,’” Kassady said.

His videos regularly receive around 100 likes, a couple dozen shares and at least 300 comments, with one video receiving more than 700 comments.

Erine Leigh commented on one video that the “codenames” Kassady assigned to council members has her crying with laughter. Costella B. Williams, who sits on the Portsmouth School Board, commented that Kassady “brings laughter to a crazy situation.” Former Mayor Kenny Wright also commented with laughing emojis, calling the comedian “crazy as hell.”

“You make Portsmouth smile,” Deanna Stanton commented on one recap. “Thanks for giving us a lightened heart in all the craziness!”

When he can, Kassady attends the meetings and has likened the past few to the iconic talent show Amateur Night at the Apollo, with audience members booing, yelling and “talking about folks’ mommas.”

He’s assigned a nickname to most council members, with Vice Mayor De’Andre Barnes labeled “Big Baby Daddy,” Mark Whitaker as “Not Quite Esquire,” Paul Battle as “Sleepy,” Chris Woodard as “Lightbulb” and Lisa Lucas-Burke as “L.L. Cool Burke.”

Kassady primarily directs his jabs at the four-member alliance that ousted Jones and replaced her with former Police Chief Tonya Chapman, asserting that residents are displeased with such actions. He makes noticeably fewer jokes about the other three — and seemingly spares Mayor Shannon Glover altogether. In one video, Kassady said he was texting with Glover during a council meeting.

In a recap of the June 14 meeting, Kassady said Battle woke up long enough to support Whitaker’s motion preventing the mayor from removing Whitaker from the meeting.

“He said, ‘Somebody getting to leave before me? I’m not going to let anybody leave before me,’” Kassady joked about Battle, who has walked out during a couple meetings recently.

Kassady joked in one video that when explaining their reasons for terminating Jones, the “Four Horsemen” — referring to the four council members who voted to fire her — might as well have included that she went to the bathroom one time and left the seat up.

Kassady teased that when Barnes spoke from behind the dais, somehow “people ended up pregnant because he’s the Nick Cannon of Portsmouth.” Cannon has seven children with four women, and another child on the way.

A 2019 Pilot article reported that Barnes, who declined to comment for this story, had five children at the time.

Kassady also quipped that Whitaker, known for viewing issues through the lens of race, likely won’t wear white underwear because he considers it oppressive.

His council recaps are an evolution of a show he did five years ago on Soundcloud, in which he sometimes discussed council happenings minus the comedy infusion.

Lucas-Burke said she’s tuned into a few of Kassady’s recent videos and appreciates the nickname he’s given her, inspired by her expletive-laced outrage when the council fired Jones.

“I think he does a quick and thorough job of providing a humorous overview of our council meetings,” she said. “He’s usually on-point with the topic matter.”

Comedy wasn’t always the plan, though. Kassady and his high school best friend made a pact to one day return to their alma mater, then named Woodrow Wilson, and take on the roles of football coach and band director, respectively, in true “Remember the Titans” fashion.

Instead, Kassady enrolled at Norfolk State University to become a physical education teacher. He started hosting campus events, but his first professional comedy opportunity was a recurring three-hour slot on a hip-hop and R&B radio show, where he came up with his Spider-Man-inspired stage name minutes before their show first aired.

Also in college, Kassady said he hosted Allen Iverson’s celebrity weekend event, which featured B.E.T. stars and athletes like Magic Johnson and Kevin Garnett.

The connections Kassady was making in his early 20s catapulted him into the comedy world, though he worked as a paralegal for 12 years to pay the bills.

Kassady doesn’t spend much time prepping before a gig, but always has a few ideas in mind. He prefers observing the crowd so he can adjust his jokes for a Jewish wedding, a church event or even an all-white older crowd. But Kassady said he also works to find commonality among people, which always outweighs the differences.

“People have kids. People have been kids. Everyone has a grandma so if you talk about your grandma, your grandma may not be exactly like mine, but she has some grandma tendencies,” Kassady said.

Other comedians and performers have tried to convince Kassady to move to New York City, Los Angeles or Atlanta for newer and broader opportunities. But, for now, he’s committed to the community where his two children are growing up. And, jokes aside, Kassady said he wants to see his hometown prosper.

In that vein, Kassady didn’t just lob jokes from afar after Tuesday’s meeting. He attended in person and addressed the council directly — as Nicholas Gordon, not Cletus Kassady. He criticized council for leaving residents in the dark.

“If you all would simply provide us with information, and know that we are, as citizens, smart enough to digest it and know what’s best for our city, sometimes rumors won’t get started,” he said. “Portsmouth is a city that if you don’t tell your story, Portsmouth will tell the story for you.”

Natalie Anderson, 757-732-1133, natalie.anderson@virginiamedia.com