Sheena Reagan, Florida’s Funniest Woman

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Photos by TS Gallant Photography

For the last six years, Cape Coral native Sheena Reagan has been making people laugh all over the state of Florida. Being the girl who was named the “Most Responsible” superlative (and never the class clown,) doing stand-up wasn’t always the clear career choice.

In 2010, at age 22, Sheena was like any other student. Unsure about her future after college, she listened for the calling that would hopefully reveal which direction to go. “When I’d ask for advice from my best friend, she would say ‘It doesn’t matter what you major in, you’re going to retire a comedian.’ I always took it as a joke, ironically,” Reagan admits.

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Her beginning in professional comedy came from a single birthday request from her best friend, Rachel. She wanted Sheena to perform on stage at an open mic night in Las Vegas, a trip they had been planning since they were teenagers. “She promised me that if I would just tell a couple of jokes at a mic for her birthday, she’d never bother me about it again. She must have known I’d be addicted after the first time,” she recalls.

Calling venue after venue for an available open mic night, Sheena and Rachel flew to Sin City and scheduled the open mic on their very last night in town. But when they arrived at the venue, it was a far cry from a comedy open mic. “I sat there, watching this big, sweaty, topless dude jam out on his electric guitar and I was devastated that I wasn’t going to be able to perform. Everyone back at home was waiting on the video, and the story.”

The manager of the bar, however, having seen her disappointment, tried to make it up to her. “He said he felt bad and told me I could tell jokes between the acts if I was still up for it. That was good enough for me!”

When she returned home, performing took a back seat and she did nothing but write comedy for an entire year. Looking for a good laugh and a shoe-in, Sheena went to the LaughIN Comedy Café in Fort Myers on a Saturday night to a sparsely attended show. When then house host, Chris Cowells, asked what she was doing there alone, she gave him an LOL moment when she asked about the next auditions. Finding this adorable, Chris put her on stage the next evening to open with five minutes. “Chris was the first to ever take a chance on me, and it changed my life.”

Time started to fly and performing was starting to become a way of life. “Comedy life is full of ups and downs. Sometimes it’s the best day ever, and sometimes you can’t help but wonder why you’re doing this to yourself.”

In 2014, Reagan entered the Ultimate Comedy Competition at the Immokalee Casino where she was unanimously “booed” off the stage after her opening line. Not one to give up, Sheena returned in 2015 and ranked in the top 5.

During 2016, the world of comedy was at a standstill for Sheena. “I had no bookings from October on. Zero. I didn’t know what to do.” Being used to comedy supplementing her income, Sheena took a second job waiting tables at the comedy club, in addition to her position as an escrow officer. “It was horrible and humbling, but at least I was in a comedy club. I’ll never be able to thank Brian and Janice enough for how much they helped me out that season,” she says.

The following spring was the beginning of comedy springing back to life. “Brian had sent me a flyer for ‘Florida’s Funniest Female’ in Boca that April. I had been off the stage for so long, I honestly would have taken any reason to tell a joke into a microphone.” Having just been through the worst drought of her comedy career, Reagan quickly signed up. She headed for the laughter, and after six months without a single professional appearance, she was named runner-up in Florida’s Funniest Female 2017.

In September of that year, Sheena left her professional job in title insurance for a fresh start in real estate and in pursuit of the love to do stand-up. “I had been thinking about it for a long time, but I couldn’t ignore the calling anymore. It was time to go.” And then along came Irma, just one day after she left her career behind. Although the real estate scene was a mess, comedy started paying the bills and continued to do so for the following months.

With a personality much larger than her stature, Sheena pokes fun at comments she’s received about her size, her dad’s cut-off shorts– which are entirely too short — and facets of life ranging from careers, dating, and the world around us. “It’s a little easier for me to tell you what you WON’T hear in my act—politics, religion, racial, gay or dark humor. I try to keep it fun for everyone. No one wants to spend their hard earned money to hear your agenda.”

People may wonder if being a performer is a glamorous lifestyle. “It’s either a hard yes or a hard no. You’re either staying in a Ritz Carlton or in a Ritz Cracker box.”

Even if there were no travel or rewards, even if I never get rich or famous, I’ll still be doing comedy. It’s who I am and I wouldn’t be me if I stopped,” Sheena explains.

Sheena’s advice to all: “Be obedient to your calling. For a long time, I wondered if this was something I was being called to do, or if it was just something I like to do. After praying on it for a long time, it was made clear to me that laughter is a healing gift! And comics can bring that to their audience, and just as important, to each other! Comics are broken people. And there’s something about broken people that are led to the mic.”

She describes herself as a “spitfire, to say the least,” when she growing up. She has a heart for veterans and the community, and her guilty pleasures are sandwiches or brownie in a cup.

To see this local award-winning comic, make plans for Sheena’s performance on July 20th at Personal Touch Catering located at 1530 Santa Barbara Blvd. Call (239) 945-2456 for tickets.