Thursday nights spills laughs at Flaco’s with Bootleggers Comedy Speakeasy

Bootleggers Comedy Speakeasy return to Flaco's Cuban Bakery for weekly comedy nights. 

The word “speakeasy” evokes a sense of desired taboo. As live entertainment is spurred as a result of the COVID-19 pandemic, the transition back to an in-person audience has been met with caution. However, comedian AJ Wilkerson is standing firm as the last beacon of laughs with Bootleggers Comedy Speakeasy in Gainesville.  

A slew of local comics is out of lockdown hibernation and performing again Thursdays at Flaco’s Cuban Bakery; Recurring features include Harry Snover, Spencer Acree and Wilkerson himself. 

“Comedy was already gaining in popularity again anyway, standup gets these societal ebbs and flows,” Wilkerson said. “There’s something different about being in the room when the laughter starts in one corner and then works its way across the audience.”  

Wilkerson’s jester journey started a year and a half ago at open mics at the Midnight bar in Gainesville. From there, he encountered Bob Smith, a veteran road comedian who put together the Keg of Laughs comedy club for showcases in Gainesville locations such as World of Beer – 34th and Woodyard Grill in Newberry. Smith conducts workshops for aspiring comics and worked with Chris Cope, who has been featured on Conan and Jimmy Kimmel Live. Wilkerson said that Smith has been instrumental in fostering the comic community in Gainesville.

Outside of Keg of Laughs, Wilkerson has also taken part in shows for University Center and High Dive and was set for an up-and-coming artist tour with Phi Entertainment before pandemic-related closures struck. Alongside dining, music and theaters, comedy took the back burner. 

“For some people, it’s like taking away water,” he said. “I was not having a good time mental health wise, not being able to do comedy. I’m autistic, so I’m very big about having a routine and having paths so not having that anymore was not really good for me.” 

Thursday nights at Flaco’s envelop a socially distanced comedy show. Wilkerson approached the restaurant with a pop-up show idea. With one night June 20 at Silver Q Billiards & Sports Bar under the Speakeasy title, he was itching to get a fresh gig for local comics cut dry in March. 

Places such as World of Beer can't hold the number of people found at previously filled comedy shows due to capacity limitations and indoor spaces. They are also unable to compensate the comics without a full audience, Wilkerson said. Flaco’s provided an opportunity in the meantime. 

“We were trying to boost up the business and we thought ‘Let’s give it a try,’” said Jill Kubisek, manager of Flaco’s.  

Every Thursday since Aug. 20, Wilkerson has gathered a guild to perform in an outdoor space at 7:30 and 10:30 p.m. He said the shows have been well-received, with tables full, all while guests and performers adhere to social distancing guidelines. 

“People want to laugh,” said Bob Smith, who attended the latest Flaco’s show. “There is so much talent it's really inspiring. There're so many people here who I know could go to the next level and higher. And having an opportunity like Flaco’s is helping propel people that way.” 

The Flaco’s appearances will be a recurring event for Bootleggers Comedy Speakeasy, but Wilkerson has plans outside of the state come the end of the year. Joe Rogan, a comedian and podcaster, will move his setup to Austin, Texas, which Wilkerson said he believes will be a new hub for comedy. With a converted camper and a Gainesville lease expiring in November, Wilkerson is making the trip.

“I’m going to Mecca,” he said.