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Comedian returns to headline in Tampa

Singleton will perform at 8 p.m. Wednesday at Peabody’s, located at 15333 Amberly Drive in Tampa.  

When USF graduate and Los Angeles-based comedian Jessica Michelle Singleton was about 10 years old, she decided she wanted to be on “Saturday Night Live.”

“I originally tried stand-up just ‘cause I wasn’t sure how one goes about getting on ‘Saturday Night Live,’” Singleton said. “The first time I did stand-up I fell in love with it, so that’s when I decided I really wanted to be a stand-up comedian.”

After graduating from USF with a degree in mass communications, Singleton moved to LA and pursued a career as a stand-up comedian. 

“When I was in Tampa you could maybe see a show once a month,” Singleton said. “Out here, I do shows every night. It’s a really great place for comedy.” 

Now Singleton is getting ready to return to Tampa for a special one-night-only performance at Peabody’s Billiards and Games on Wednesday at 8 p.m. It will be her first time performing in the city where she got her start more than four years ago.

Singleton performed her first stand-up show at Side Splitters in Tampa. At the time, Singleton was unaware her first experience with open mic was part of the opening round for Florida’s Funniest Comedian. 

“The first time I got on stage was incredible,” Singleton said. “The second time … they told me I had to be clean and I didn’t know what that meant and I wrote an awful dorky clean set, like G-rated … and I bombed.”

Since then, Singleton has had a lot more practice and is looking forward to showing what she’s learned. 

“When I left, I was kind of an open mic level comedian,” Singleton said. “I’ve done a lot of work in the last four years and I’ve really grown. I have a full headlining set so I think that it will be very exciting. I get to show people that I’m actually doing comedy.” 

Because Singleton is based in LA, most of her tours stick to the West Coast and a Tampa performance was just too costly. However, after she was invited to a friend’s wedding in the area, she saw her chance to once again perform in the city where she began her career. 

“I’ve been trying to incorporate Tampa somehow into my road travels but it just hasn’t worked out,” Singleton said. “I haven’t had the best of luck communicating with the comedy club down there. I think a lot of it’s because I started there… they haven’t seen me grow.” 

“I have a lot of observational material,” Singleton said. “… I would say it’s a pretty good mix between personal family storytelling and observational.”

Currently, Singleton said a lot of her set is based on her observations of women and dating, and she said she pulls inspiration from comedy greats such as Joan Rivers and Louis C.K.

Last year Singleton participated in the Montreux Comedy Festival in Switzerland, the largest and longest running comedy festival in Europe. Out of the thousands of applicants, only five English-speaking comedians were invited. 

“I got to perform for an international audience, which was incredible,” she said. 

For other comedic hopefuls, Singleton said the key is to write a lot and get in front of an audience as often as possible. 

“It’s not easy,” Singleton said. “You don’t become a star overnight. It’s a lot of hard work for basically nothing upfront.”

Singleton would still like to one day get on “Saturday Night Live,” but not in the way she originally planned. 

“I would be totally happy being a writer for ‘Saturday Night Live,’” she said. “There was a point where I would not have been OK if they would have been like ‘yeah we could take you as a writer,’ but now I just enjoy creating comedy so I’m kind of open to anything where I get to use my abilities to make people laugh in one way or another.”