Now in its 22nd year, the Headdress Ball has established itself as one of Orlando’s most elaborate—and outrageous—black-tie affairs. The event offered nonstop entertainment from the moment guests arrived for the V.I.P. party at 6 p.m. until the after-party finished at 2 a.m. The main show in the ballroom was an elaborate Las Vegas-style spectacle produced by JM Best Entertainment and Hardrive Productions, with a cast of 75 performers, six female impersonators, and singer Jessica Sutta, formerly of the Pussycat Dolls.
“We work with a lot of these vendors throughout the year and then when we call on them to support the charity, they do. And they bring a lot to the table to help us make it bigger and better every year,” said John Best, owner of JM Best Entertainment, which has produced the event for nine years. “When you are in the middle of a project, it’s the easiest time to think ‘This is what we should do next year.’ Last year, Greg Brown from Hardrive said, 'Let’s do a circus theme!' Then it takes months to figure out what the stage is going to look like, what the lighting’s going to look like. And now we already have ideas for next year’s show.”
The evening began with a reception for guests who paid at least $350 per ticket (some paid as much as $1,500). The center of the room showcased a variety of performers such as aerialists from Metropolis Productions and a juggler from Hardrive Productions. Sponsor Ketel One served custom cocktails from an ice luge—a three-foot-tall ice sculpture of a Ketel One bottle.
At 7:15 p.m., nearly 1,000 guests—up about 5 percent over 2010—filed into the main ballroom. For the first time, organizers created a runway down the middle of the room so the seven companies that entered the headdress competition could parade their creations closer to the guests. Additional entertainment included a laser show from LSDI and scantily clad men and women dancing on platforms positioned around the room. Throughout the night, guests stuffed bills into the women’s G-strings and the men’s bikini-style trunks, with all of the money going to the charity.
While attendees enjoyed a three-course meal and continual entertainment, a team of 25 volunteers transformed the V.I.P. reception room into the setting for the after-party, which offered additional entertainment from Hardrive Productions.
