Nothing says “Fantasy Fest®” more than feathers, glitter and glue. And you’re guaranteed to see a lot of it during Key West’s 43rd Annual Headdress Ball which is coming up on Thursday, October 22.
Produced by the Key West Business Guild, this year’s outrageous costumed extravaganza embraces Fantasy Fest’s® 2026 theme: “Musical Icons & Iconic Musicals.”
Internationally acclaimed performer and Key West icon, Randy Roberts returns to headline another off-the-charts night of creativity, glamour, and entertainment.
Yes, we all know that there are a ton of great costume parties during Fantasy Fest’s® 10 days of debauchery, but rest assured, this is no run-of-the-mill costume competition. No, no, no — the Headdress Ball is heads and shoulders above the rest of the pack. Expect to see truly amazing works of art exuding a dreamlike world of fantasy and musical mayhem.
With a First-Place Prize of $5,000 and over a dozen contestants, the competition is always fierce. But what makes this spectacular contest so unique is that the contestants are only judged from the shoulders up. Entrants have been known to combine laser and LED lighting, fog machines, and even intricate moving parts into their one-of-a-kind headdresses.
Also on the roster: special guest performers, surprise entertainment, and an immersive pre-party. With Key West’s legendary DJ, Rude Girl, spinning a high-energy soundtrack, it’s one fantastical night that typically draws upwards of 500 people. Gates open at 6:30 pm for the pre-party. Main Stage show starts at 8 pm with VIP table seating, chairs, and lawn seating available.
So be sure to mark your calendars for Thursday, October 22 (Rain date: Friday, October 23). Key West’s 43rd Annual Headdress Ball takes place at the Coffee Butler Amphitheater in Truman Waterfront Park, 21 E Quay Rd.
Heads Up: This show ALWAYS SELLS OUT, so snag your tickets early at keystix.com. More info at 305-294-4603; gaykeywestfl.com.
BTW: Catch the fabulous Randy Roberts and his tour-de-force one-man show at La Te Da’s Crystal Room Cabaret, 1125 Duval St, Key West. Tickets and info: 305-296-6706; lateda.com.
Randy Roberts Shines — Lip Gloss and Pumps…Or Not
Randy Roberts has always been a bit of a ham. Starting with his stage debut in Norfolk, VA, in the Temple Israel Thanksgiving tableau, where he famously said, “Turkey again, Oy!” he has been addicted to the spotlight.
From Las Vegas to San Juan, New York City to Madrid, Randy has dragged his drag around the world, entertaining audiences for almost forty years (that’s a lot of lip gloss) in casinos, cabarets, clubs, and theaters.
He’s spent the last two decades performing his one-man show — “Randy Roberts LIVE!” — in the Crystal Room Cabaret at La-Te-Da in Key West. “I call it a tribute to the most famous and infamous ladies of the stage, screen, and in my mind. I bring ‘Bette Midler,’ ‘Cher,’ and my own character, ‘Randy Roberts’ to life.”
No lip-synching here: Randy sings all the songs live. And he does it very, very well. So well, in fact, that he made it to NBC’s hit show, “America’s Got Talent” and also appeared on ABC’s former award-winning daytime drama, “One Life to Live.” And while Randy hasn’t made it to Broadway yet, he has co-starred with acclaimed actor, Alan Cumming in the indie film “Any Day Now,” and has also appeared on nearly every stage in Key West — in and out of drag.
“I used to sing a song from the Broadway show ‘Pippin’ called ‘Corner of the Sky.’ I can honestly say that in Key West, I’ve found mine!”
You can catch “Randy Roberts LIVE” in the Crystal Room Cabaret at La-Te-Da in Key West. Tickets and info: 305–296–6706.
