The 27th annual Headdress Ball, Tuesday, is one of Fantasy Fest's biggest official costume contests and show featuring live entertainment. </p><p>Sponsored by the Key West Business Guild, this party attracts between 25 and 30 contestants along with hundreds of attendees. </p><p>Hosted at the Southernmost Hotel, South and Duval Streets, under a huge double tent, this year's theme is "Hedonistic Heroes and Vexing Villains."</p><p>Contestants make the most of the themes provided by the Headdress Ball committee. For last year's "Raucous Caucus" theme, the winner was Lisa Morris with a headdress sporting a live duck seated in a miniature wheelchair.</p><p>The political campaign-style button read "George, the Lame Duck."</p><p>"It was hysterical. Very cleverly crafted, but hysterical," John C. Giuliano, executive director of the Guild, said. While some of the costumes are full-body ensembles, the judges only award points from the neck up. </p><p>Feathers, fabric, mechanized moving parts and lights are established elements. Prizes include $1,000 for first, $300 for second and $200 for third place.</p><p>"This year's theme is Hedonistic Heroes and Vexing Villians," Headdress Ball Chair Peter Arnow said. </p><p>The Headdress Ball is the major fundraiser for the Key West Business Guild, one of the oldest gay and lesbian chambers of commerce in the country. "The funds raised enable us to continue our mission to promote Key West as a premier destination for GLBT travelers and their friends and family while providing services and support to the Guild's business members and the community at large," Giuliano said. </p><p>A huge show directed and emceed by WEOW 92.7's Rude Girl and friends, will include Key West's Super Girl, Michael McCabe and Red, a former Fantasy Fest Queen who returns for an encore performance. </p><p>Vocalist Lenore Troia will provide pre-show entertainment. Also on tap for Tuesday's show are the Key West Burlesque Dancers and The Keys, a Key West piano bar, will send over some of their talented performers in from NYC. Maya Montana from Aqua Night Club, Lee and Jake from the Bourbon Street Pub and a number by the Key West Contemporary Dance company are also on the bill. </p><p>All partygoers are encouraged to wear head gear. "Even if it's just a ball cap with a feather in it, everyone should have a headdress on," Arnow said.</p><p>VIP seating is available in front of the stage and general admission guests can also get a close- up view on closed circuit TVs broadcasting the event. The doors open at 7 p.m. at the Southernmost Hotel.</p><p>Premium tables cost $320 and regular tables go for $270. (The tables seat four), $40 for general admission. Visit www.keystix.com. </p><p>Headdress Ball 2009 is sponsored by: Cypress House, Key West Bank, Southernmost Hotel Collection, Equator Resort, The Keys, a Key West Piano Bar, Alexander's Guest House, Doug Mayberry Real Estate, Key Lime Commercial Real Estate Services, The Mermaid and the Alligator, Rent Key West Vacations, 901 Designs and Signs, Island House, Solares Hill Design Group and Travelhost Magazine. WEOW/92.7 is the official radio station for the event and Rude Girl will be interviewing the entertainers on her morning program. </p><p>The Headdress Ball is an outgrowth of Fantasy Fest's earliest beginnings and was first held 27 years ago at the Monster Bar on Front Street.