Florida Entertainer of the Year made its anticipated return in 2023, welcoming 600 people to The Ritz Ybor for an elevated evening of local and legendary drag. The Tampa-based pageant is one of nearly 20 preliminaries around the country, all of which serve as a springboard for drag artists to compete at National Entertainer of the Year.
The nationwide competition was conceptualized decades ago by George Stinson and Ed Lewis, who owned Louisville, Kentucky’s celebrated-but-defunct Connection Complex Nightclub. They were inspired by Female Impersonator of the Year, a Texas-based pageant held in 1985.
Over 30 queens have been crowned since 1991, including Central Florida’s Trinity “The Tuck” Taylor. She competed and won National EOY in 2014 before becoming a fan favorite victor on various iterations of “RuPaul’s Drag Race.”
“Pageantry as a whole is just something different. It’s not gone mainstream, like what people see with ‘Drag Race,’ and for me specifically, pageantry is really what built me into the entertainer that I am,” Taylor says. “I started doing pageants when I first started doing drag and EOY was the first major system that really took me in.
“I competed for 10 years in the system, and it’s really what introduced me to people that I know today,” she continues. “It was like a finishing school for me and it’s important because it really does help people get connected to others in their community.”
Eight contestants entered last year’s Florida EOY, vying for $5,000, a crown, sash, certificate and hotel stay for National EOY in Kentucky. They were judged on their presentation, creative evening wear, an on-stage question and answer session and specialized talent.
After the scores were tallied, Florida EOY sent winner Kenya M. Black and first runner-up Twila Holiday to nationals, two fan favorite queens from Central Florida. The latter ultimately captured the crown.
Holiday says her path to victory began with Taylor, long a cheerleader for the system and now a one-third owner of National EOY. The “Drag Race” alum also helped guide Florida EOY organizers Neil and Katie McCurry through their first year as promoters.
“Trinity approached me literally the week of the pageant,” Holiday explains. “She said she thought I’d make a great contestant and at the time I had never thought of competing in EOY. It wasn’t in my immediate future.
“I said, ‘I don’t have time to invest and really prepare for a pageant, but I’ve got a decent drag wardrobe. I think I could throw something together,’” she recalls. “So that’s exactly what I did. I decided to do the pageant two days before I showed up for registration — we put our little package together and came in first alternate.”
Holiday won three of the preliminary’s four categories, all but her Liza Minelli-themed talent.
“I wasn’t able to secure dancers for it, which I knew was going to be an issue,” she says. “But the overall experience for Florida EOY, going in having never competed in an EOY pageant, was remarkable. It was honestly the best experience I had ever had.”
That’s thanks in large part to the McCurrys, who Holiday says “went above and beyond” as promoters. The two were also recognized for their efforts at nationals.
Florida EOY won preliminary of the year in 2023. Neil calls the accolade “a big honor for us, particularly because there are so many other great prelims out there.”
“When Trinity approached us about doing this, Katie and I said we had to really go big or not do it at all,” he explains. “That was the approach we took with it. We spent a lot of time thinking about what the pageant would look like — from the flow of people walking in the door and what their experience would be like — to the ancillary things happening around them like meet and greets.”
The McCurrys worked diligently to conceptualize the preliminary from start to finish. The evening featured entertainment from “RuPaul’s Drag Race All Stars” winner Kylie Sonique Love and other talents.
“The stage presentation, the lighting scheme, we were very pleased with all of it,” Neil says. “So to be recognized by our peers as the event of the year was a great, great experience for us.”
Taylor says the recognition was well deserved.
“Last year’s preliminary was like a national pageant in itself,” she notes. “It was run like a national pageant with the entertainment, the lineup, the judges, the location. The way that Neil and Katie put it together was like none other.
“They are so passionate about supporting the community and we’re very fortunate to have them as promoters in our system and as allies for our community,” Taylor continues. “Last year’s event was so spectacular and this year is supposed to be even better. They’re not newcomers to the system anymore and they really know what pageantry is all about. I’m excited for the community to have something like this for everyone to enjoy.”
Neil expects up to 10 contestants for this year’s preliminary, which returns to The Ritz Ybor April 7 at 6 p.m. They’ll compete for a $5,000 total cash prize, a crown, sash, plaque and four-night hotel stay at nationals, once again being scored on presentation, creative evening wear, on-stage Q&A and talent.
This year’s theme is Disco, which Neil says was chosen “to bring joy, laughter and put some dance in everyone’s step.” The McCurrys promise “an unforgettable evening of glamour, talent and fierce competition for an all-star drag pageant.”
“People that were there last year can expect the same energy, talent and excitement they had before,” Neil says. “They might also notice subtle differences that were designed to make the event even better.”
As for those who didn’t attend, he says “they’re going to experience what we consider to be a national class type of event, one that rivals anything they could see in Miami, Los Angeles, Chicago or New York, as far as the production and talent value.”
In addition to each contestant’s presentation that evening, local and national fan favorites will also appear. Central Florida entertainer Addison Taylor will emcee and the evening will also feature Holiday as National EOY 2023, Black as Florida EOY 2023, Taylor as National EOY 2014 and Tiffany T. McCray, celebrating a decade as Florida EOY 2014.
Other system favorites schedule to appear include National EOY 1994 Electra, 2004’s Tasha Long, 2009’s Bianca Nicole and 2018’s Danielle Hunter. Current “RuPaul’s Drag Race” season 16 contestant Nymphia Wind will also perform, spreading both disco and “banana fever.”
“As a drag pageant we want to represent emerging local drag talent, but we’re also happy to showcase legends from ‘Drag Race’ like Trinity and Nymphia,” Neil says. “She’s one of the most popular contestants in the midst of a really competitive season. We love showcasing artists in different stages of their career.”
The McCurrys’ appreciation for all levels of drag is something Taylor holds dear. It’s also what’s kept her invested in pageantry over the years.
“This is my 21st anniversary of doing drag and I was a local artist far longer than I was anything on TV,” she notes. “I know the struggle of how expensive it is to do drag when you’re not making TV money. I know the struggle of dating as an entertainer and trying to get a fair paycheck and bookings. Not only to support your art but to support yourself while doing your art.
“I think it’s super important that we support local entertainers so this art form doesn’t die and so they feel validated and appreciated so that it’s taken seriously as a job,” she continues. “Because a lot of people use it to pay for their bills and live. We need to support these artists.”
One way to do that is by supporting Florida EOY.
“EOY has a stronghold in Florida because we have so many former winners from the state,” Taylor says. “It’s important that we continue that legacy and Neil and Katie have been paramount to that, pushing this preliminary above and beyond anything that’s ever been. If you’re looking for a good pageant to come and support, it is definitely this one.”
Holiday agrees. The drag artist is currently touring the country for EOY preliminaries and is excited to reign close to home.
“I always say that before ‘Drag Race,’ in order to be a notable drag queen in the community, you had to compete in pageants,” she says. “That’s how you got bookings. That’s how you got exposure. That’s how you became a legend.
“TV has kind of changed that but I’m an old school queen and I love, love, love to promote pageantry,” she continues. “EOY is the perfect platform for entertainers to make a name for themselves and now’s the time to get on board while we have the momentum rolling. This is world class pageantry and is going to be a night to remember.”
Tickets for Florida EOY 2024 are on sale now and begin at $19.95 with additional fees. Meet and greet opportunities are also available.
“Drag is, without question, a serious art form and a great form of entertainment,” Neil says. “We take our commitment to bringing world-class drag to the Tampa Bay area seriously and we’re really fortunate to be part of EOY. You’re not going to find a better place to be on April 7 than the Ritz Ybor for this celebration of drag and community.”
Florida Entertainer of the Year will be held April 7 beginning at 6 p.m. at The Ritz Ybor, located at 1503 E. 7th Ave. in Tampa. For more information and to purchase tickets, visit FLEOY.com.
