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Live Music in Key West

By Wayne Faust

Key West has always been a hot spot for live music. When tourists finally get to the end of the road after making the long trek down the Keys, it does something to their psyche. Normally respectable citizens of the mainland tend to breathe in the free air of the tropics and start doing some pretty uncharacteristic things – things like drinking rum runners and stripping down to barely perceptible clothes. And they naturally congregate on Duvall Street, where the local clubs are happy to contribute to the anything-goes atmosphere. Live music pours out of nearly every bar.

The music leans heavily towards a Jimmy Buffett, island-flavored sound, and you’re sure to hear “Brown-Eyed Girl” at least ten times a night from ten different clubs. And that’s as it should be, because everyone is usually in an island kinda mood. But there is much more to be found. You can hear jazz, reggae, hard rock and blues, from places like Rick’s, Sloppy Joe’s, The Bull, La Concha, The Hog’s Breath, and, if you don’t mind walking an extra ten blocks or so, Jimmy Buffett’s own Margaritaville Cafe. What makes the whole scene so appealing is that most of the clubs are open to the outside, and all this music makes a potent gumbo of sound in the humid air as you walk down the street.

Long ago, before there was ever a road to Key West, most of the town was populated by pirates, who helped to ‘salvage’ goods from ships that were wrecked on the reefs because someone had switched the signal lights around. Everyone knew who switched those lights in the first place, of course. But salvaging was a tempting, lucrative profession in those days. That outlaw spirit still lives in Key West, and it can be heard in the music of performers in the clubs and from street performers on nearly every block.

I personally got to experience healthy doses of Key West music every April for 15 years, when I played at Sloppy Joe’s with the duo Faust and Lewis. We developed our music and comedy act on that famous stage, and wrote gobs of funny songs about life in the islands. We always did the 5-9 PM shift, so after our show there was plenty of time to do the Duvall Crawl and check out the other acts in town. I became a great fan of Hugo Duarte, who was performing at the Hog’s Breath Saloon late one night in early April. It was uncharacteristically cool that night, with the temperature all the way down in the low 60’s, but my wife and I braved the chill to listen to Hugo for over an hour. His original songs are nearly perfect, and tell great stories about life in the islands, and about ship captains heading somewhere down south.

I also got to know Terry Cassidy, who still does afternoons at Sloppy Joe’s. He adds a smooth, bluegrass feel to his island music, and his song “Hooked On the Easy Life” just about sums up the attitude of the locals.

Pete and Wayne currently handle the 5-9 shift at Sloppy’s, and you can be sure they are continuing the “What Me Worry?" attitude down there, with their adult humor and songs.

There are so many more artists that have made a real splash on the Key West scene. Pat Dailey, the legend of Lake Erie, has been performing in February and March at Sloppy Joe’s for over twenty years. Bill Wharton, The Sauce Boss, one of the finest blues players I’ve ever seen, also makes hot sauce during his shows and serves it up in gumbo to people who stay around until the end. He makes regular appearances at Margaritaville. Ben Harrison, who with his wife Helen own Harrison Gallery, is also a renowned singer-songwriter who puts on mini operas about some of the colorful characters in Key West history, including a guy who kept his wife’s body in his parlor for years after she died.

All of us who have performed and written songs about Key West owe a tremendous debt to Shel Silverstein, who lived in Key West until his death several years ago. Shel wrote many famous songs, including “The Unicorn Song,” and “Cover of the Rolling Stone,” as well as countless award-winning children’s books, including “Where the Sidewalk Ends.” He generously gave of his time and talents to mentor songwriters that made their way to Key West. I personally spent an afternoon at his house, and I knew I was truly in the presence of greatness.

I recently did a weekend back at Sloppy Joe’s for the first time in four years. You can rest assured that the music and fun continue on, as vibrant as ever. Maybe it’s the gulf breeze. Maybe it’s the rum runners. Whatever it is, I hope it goes on forever.

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Wayne Faust is a music and comedy performer, who also runs Picklehead Music, a site devoted to showcasing funny music, along with some great acoustic and variety CD’s. Incidentally, Picklehead has a section devoted exclusively to Key West Artists, with more CD’s added there all the time.-

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