Editor’s Note: T-minus 51 days until the 2026 Fantasy Fest parade. Join the Keys Weekly each week for exclusive Fantasy Fest features highlighting the people and projects behind the island’s biggest annual party.
Local hip-hop artist Mike Stack is about to join a venerable group in Key West — the grand marshals of the Fantasy Fest parades. The first parade took place in 1979 and was, by all accounts, a scrappy and loveable DIY affair. The party quickly scaled up, and in 1983 Tennessee Williams led the festivities as the first grand marshal. Since then, several notable figures have held the reins on that first float, including actress Kelly McGillis (1991), athlete and author Diana Nyad (2013), and paranormal expert David Sloan (2024). Each has imparted their own flavor into the parade, and Stack looks to be no exception.
When asked how it feels to be approached, his initial reaction is a resounding, “Let’s go! I’m excited to lead the way. I’m about to grand-marshal the heck outta Duval!” Expressing gratitude to the festival organizers, Stack, who is perhaps best known for his song, “I’m from Key West” written with D-Lew, said the phone call felt a bit like being inducted into the hall of fame, especially for someone born and raised in Key West, who has attended Fantasy Fest his entire life. The 2026 theme is “Musical Icons and Iconic Musicals.” Always modest, Stack said he doesn’t classify himself that way but appreciates the festival recognizing his ability to hold a crowd.
After the initial shock wore off, Stack dove right into planning the party. “They told me I can do whatever I want. They shouldn’t tell me that, though, because I’ve got a big imagination.” His vision is essentially a concert that travels the length of Duval, with fans dancing along with the float the entire way. He’s already recruited sound and lighting techs, a few other local artists and DJs, and his “right-hand man,” D-Lew. As for the fans, he plans to send out a mass text inviting anyone who wants to take to the street that night, to join the moveable show. “We’re going to take over Duval, we’re ready to have some fun. I want to look back and say, ‘Remember that time I was grand marshal?’”
It’s not all parade prep for Stack, though. Just a couple weeks prior to the big event, he’ll be hosting the second annual Stack’d Festival Oct. 9-11. The weekend features free shows all over town, ranging from a heavily produced concert at Sunset Pier to more casual pool parties, acoustic showcases and nightly DJ sets. The energy he pours into that weekend proves that Fantasy Fest chose the perfect candidate to kick off the biggest party of the year in Key West.
