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 prefer drinking rum runners and stripping down to barely perceptible clothes. And they naturally congregate on Duvall Street, where the Local venues 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 are sure to hear “Brown-Eyed Girl” at least ten times a night from ten disparate club s. And that’s as it should be because everybody is a lot of the time 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, the majority of the town was populated by pirates, who advocate ed to ‘salvage’ goods from ships that were wrecked on the reefs because a person had switched the signal lights around. Everybody knew who switched those lights in the 1st 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 venues and from street performers on nearly every block.

I individually 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 tunes about life in the islands. we always did the 5-9 PM shift, so following our show there was plenty of time to do the Duvall Crawl and check out the other acts in town. I became an excellent 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 tunes are nearly perfect, and tell excellent stories about life in the islands, and about ship captains heading somewhere down south.

I additionally got to know Terry Cassidy, who still does following noons 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 Regional s.

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

There are so a lot of more performers 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 have ever seen, also makes hot sauce during his shows and serves it up in gumbo to individuals 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 following 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 a few 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 individually spent the following noon 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 may 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.

Find more live music venues and tickets for concerts in Florida at concerts50.com.

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