8 top comedians visit Lexington over 6 weeks and you can play ‘Office’ trivia with one

As summer begins to come to a close, Lexington is about to fall into comedy season.

Over the next six weeks, eight big-name, experienced stand-up comedians will play the city’s venues, big and small, from the intimate Comedy Off Broadway to the revered Rupp Arena. Some are in the middle of nation-wide tours while others are getting out to work on new material, something Comedy Off Broadway embraces, having welcomed many A-list comedians to its 250-seat club since it opened in 1987.

These well-known names have hosted White House Correspondents Dinners, headlined hit movies, racked up Netflix specials, starred in or created popular network TV shows, spawned viral moments you’ve probably shared on your social media and hosted weekly podcasts for millions of listeners.

Plus, you can even play a round of trivia with one of them.

But why are so many great comics coming and why do so many of them keep coming back to Lexington? The shows are part of a priority for downtown Lexington’s Central Bank Center, which runs Rupp Arena and the Opera House. Thanks to years of groundwork laid by Comedy Off Broadway, Central Bank Center has recently ramped up their comedy offerings with big name arena shows like Jo Koy, Bert Kreischer, Jeff Dunham and Jim Gaffigan. And they have been taking advantage of the 950-seat Lexington Opera House for more intimate shows including being the setting for a Netflix taping for comedians Heather McMahan.

Roy Wood Jr.

When: Aug. 18-19

Where: Comedy Off Broadway

Since we last spoke to veteran stand-up comedian Roy Wood Jr. back in 2019, some globe-altering events that affected everyone definitely took place and had everyone talking.

“I had my third hour(-long) special in 2021. That’s what it is,” he joked.

All kidding aside, Wood Jr.’s career has continued upward, going from a correspondent on “The Daily Show” to being asked to host the White House Correspondents Dinner in 2023. As he takes time away from the news desk and occasional podcasting to take his new hour of material on the road, he said he will soon begin to shift from his forte of tackling topics from varied and unexpected perspectives to examining himself and his own life in future material.

“I’m talking about things that make me laugh, and I hope you will join me,” he said.

Carlos Mencia

When: Sept. 1-2

Where: Comedy Off Broadway

The man who first found mainstream fame on television as the brain behind Comedy Central’s “Mind of Mencia” is back on TV as a voice actor for the popular Disney+ animated show “The Proud Family: Louder and Prouder.” And he continues to tour doing stand-up, his first love in comedy, and is touring to bring his latest material to smaller clubs across the country.

Dave Chappelle

When: Sept. 12

Where: Rupp Arena

A lot has happened since Dave Chappell last headlined Rupp Arena. The man behind one of the most popular sketch comedy shows of all time, “The Chappelle Show,” has now become one of the biggest and, occasionally, most controversial comedians on the planet.

He brings his singular voice to Lexington this year for his “It’s A Celebration” comedy tour. Ticket prices start at $39 and the show will use every seat in Rupp. But be warned, the show comes with restrictions: No cellphones, cameras or recording devices will be allowed; all phones and smart watches must be secured in locked Yondr pouches.

David Koechner featuring ‘The Office’ Trivia

When: Sept. 14-16

Where: Comedy Off-Broadway

People have the choice of two unique experiences if they decide to come to see comedic actor David Koechner perform in Lexington. The first is a more traditional evening of stand-up comedy where the actor of “Anchorman” fame talks about everything from love and divorce to manatees and gravediggers. The other is an afternoon trivia night centered around the popular NBC comedy “The Office,” where Koechner dons his beloved Todd Packer persona to host.

“I always thought ‘Anchorman’ was the greatest thing I’d ever done,” Koechner said. “Then, it started saying David Koechner from ‘The Office,’ and I was like, ‘Really?’”

Koechner said he came up with the idea to do a fun service to the faithful fan base that includes trivia and even a showdown between the Top 2 teams that will involve acting out a scene with Koechner in character to determine the winner. This event is also followed by a meet-and-greet. Whether you go to his stand-up, the trivia night or both, Koechner promises to give people an experience to remember.

“I like to feel like I never short-changed any audience,” he said.

Tim Dillon

When: Sept. 21

Where: Lexington Opera House

As a podcaster, cultural commentator and comedic provocateur, Tim Dillon has garnered millions of devoted listeners with “The Tim Dillon Show” and plans to publish his upcoming book “Death to Boomers” this fall. Until then, he plans to bring his “American Royalty” comedy tour to the regal setting of the Opera House.

Kevin James

When: Sept. 28

Where: Lexington Opera House

Many people know Kevin James from the hit sitcom “The King of Queens,” various movie collaborations with fellow comedian/actor Adam Sandler and solo hits like “Paul Blart Mall Cop” and “Zookeeper.” But James started as a hard-hitting stand-up comedian and is returning to his roots with his latest outing, “The Irregardless Tour.”

Trae Crowder

When: Sept. 29

Where: Lexington Opera House

The Tennessee native, who first went viral with his comedic and insightful rants on political issues with his Liberal Redneck persona, later found himself pursuing stand-up comedy full-time. On stage and in media appearances, he became a fan favorite, offering comedic takes on politics and culture. Crowder was originally supposed to perform at the Opera House in July but had to reschedule due to structural issues in the venues balcony. He will honor his commitment in the space next month in his “Just Me and Y’all” comedy tour.

Tom Segura

When: Sept. 29-30

Where: Comedy Off Broadway

Tom Segura is fresh off the success of his latest Netflix comedy special, “Sledgehammer,” and riding high as a popular podcaster from shows like “Your Mom’s House” with wife and fellow comic Christina Pazsitzky and “2 Bears 1 Cave” with popular comedian Bert Kreischer. While Segura played numerous theaters and arenas on his most recent world tour, he is giving fans a unique opportunity as he tours smaller clubs to work out new material for his next tour and hour-long special.

Tickets for his four shows at Comedy Off Broadway sold-out fast, but you could always try the secondary market.