The South's Best Bar 2019: Sloppy Joe's

Like a rare Cuban rum, this dive just gets better with age.

As a longtime resident of Nashville, I can sniff out a touristy bar like a funnel cake at the fair. The cover bands, the crowds, the Bud Lite bottles tossed like clanging cymbals into trash cans. We have them on Broadway just like Key West has them on Duval Street. But some bars have too many layers of history and dust on the ceiling fans to be dismissed as just touristy.

Sloppy Joe's has existed in Key West since the 1930s, one legend suggesting Hemingway named it after the floors in a favorite Cuban spot—perpetually sloshed with spilled alcohol and melting ice. White stucco and brick form the boxy structure with shutters thrown open to catch a breeze. A rowdy and independent bunch of islanders drank here, and it's still a workhorse of a bar. Open 365 until 4 a.m.

My own story with Sloppy Joe's began two weeks before my 21st birthday when I got busted at its doors with a fake I.D. I didn't visit again until two weeks shy of turning 40. No one bothered to card me on that visit.

Yet another time, my husband and I slipped into Sloppy Joe's to escape a crowded street party. From frying pan into the fire, we squeezed into a packed house to sip two pina coladas, neon red cherries bobbing in a pool of dark rum on top. We somehow felt revived.

The next day we repeated the visit, and then two times became tradition.

Sometimes we sip our pina coladas at the weathered bar between Dutch accents fresh off cruise ships while a piano player bangs out covers. Still, the place feels democratic, a catchall where lots of different folks feel welcome. Once when we visited during the annual Hemingway Look-Alike Contest, a hundred "Papas" serenaded the place in exaggerated baritones.

Sloppy Joe's has history in Key West, but I've made my own history there, and that's part of what makes a good bar. A guy in ball cap next to a man in fedora? Six women squeezing together for a photo? Tourists, maybe. But every person seems to be having a blast. Just trying to beat the heat, yet none of them trying to be cool.

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