Key West knows how to put on a show. There are the week-long costumed shenanigans that constitute Fantasy Fest, of course, but you can also find at least three different flavors of drag, burlesque, cabaret, Jimmy Buffet, barroom crooners, bands, karaoke and an incredibly dynamic theater scene.
You might say performance of one kind or another is the signature art form here. Yes, Ernest Hemingway forever linked the island with literature, and the visual arts will always be an integral part of such a spectacularly picturesque place. But performance — theater in particular — has been an exciting constant for as long as anyone can remember, and it shows no sign of waning.
The season typically kicks off in December when the Waterfront Playhouse and Red Barn Theatre stage the first in a roster of six to eight high-caliber productions. Timed to coincide with the arrival of theater-savvy snowbirds, a real excitement courses through Key West as productions are anticipated, experienced and discussed almost universally. The Producers, Enchanted April, Buyer & Cellar, The Skivvies and A Streetcar Named Desire are just a few of the shows presented by these two companies just this season. Most casts include a healthy mix of local talent and professionals from out of town, which only adds to the buzz, as friends are eager to support their friends on stage.
Not to be outdone, Fringe Theater Key West — celebrating its fifth anniversary season — Theatre XP, the always amazing Burlesque at 801 and Tennessee Williams Theatre roll out their own schedules of locally produced performances and national tours.
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This is no small feat for an island that’s just 7.4 square miles across and has a permanent population of 25,000. Unlike writing or painting, theater has a significant fiduciary burden and relies primarily upon a loyal audience to pay for the professional actors, directors, backstage crew and year-round overheads that make it all possible.
In 2015 Michael Marrero, a successful photographer and Key West local, threw his hat into the ring. He founded the Key West Theater, moving it into a spectacularly renovated space that had been dormant for 20 years. Describing itself as a performing arts center, Key West Theater stages original plays, musicals, films, concerts and more. It’s a bold step, but Marrero is eyeing a younger demographic settling into the island down the road, bringing with it a new set of entertainment interests.
Once upon a time, Key West’s stages went dark when the humidity rolled in and the snowbirds flew back home. Nowadays, the season lasts longer than ever. So, if you are planning a visit in the coming months, there’s plenty of drama in store.