When I was in my late 20’s, around 1987 or so, I lived in Marathon, Florida, had my captain’s license and worked big-game charter boats in Marathon and Key West. Fishing was awesome year-round but paid charters were very slow June through October so I would look for other ways to make money.
My first gig in Marathon was as a radio DJ at a local station but my most memorable side job was working as a bouncer in Jimmy Buffet’s Margaritaville Bar and Café in Key West.
I saw the doorman job advertised in the Keynoter, a local newspaper and drove the 55 miles down to Key West from Marathon to apply. I remember sitting at the bar filling out the application. I think I got the job because I worked out 4 times a week, had a blond ponytail, all my teeth and a college education.
The work was easy, I was there more for show than anything else. Be polite to the customers, check IDs, collect cover charge when bands were playing and come inside FAST to help if the bartender threw ice at the door from the inside, which was a sign for trouble.
The staff there was amazingly friendly, and the bar manager was cool if I showed up a few minutes late on the occasional day I ran a fishing charter in Marathon before driving down for a 6:00 pm to 1:00 am shift.
Margaritaville in the 80’s was a typical Duval Street bar and grill with front windows that were up and open during the daytime and a stage for musical acts in the back. I spent most of my nights there standing outside the door to the left of the gift shop watching the people go by and trying to look welcoming.
Working nights at Margaritaville was a lot of fun. Duval street at night was always a bit of a parade with people from all over the world, of all types, walking by in all stages of drunkenness. I checked ID’s, gave directions, answered the most asked question [Is Jimmy Buffet playing tonight?] and directed the occasionally significantly drunk person away from entering.
I also got to know the street residents and other people in the industry who worked up and down Duval street. There was a homeless guy named Harpo who had a severe limp and a major drug problem. He looked deranged and fierce, making eye contact with him would give you the signal to steer way clear. He was also heavily muscled. Even the cops gave him a wide berth.
One night he staggered down the sidewalk, stopped in front of Margaritaville and asked if we had anything to eat. Out of kindness I asked one of the waitresses to get him a hot dog and fries. He was very grateful and from then on I always got smiles and friendly conversation from Harpo, even when I had to ask him to move along because he was creeping out customers.
Side note on Harpo, five or six years later when I returned to Duval street for my bachelor party, the attendant where we parked the car was Harpo. He had cleaned up his act, was sober and had found a sponsor to help keep him on a path to recovery. It was really good to see someone come back from rock bottom and move on with their life.
Other notable street people were the bicycle rickshaw drivers who would ferry people up and down Duval street and take a few minutes to talk about what was going on in town, show off new tattoos and just shoot the shit. The only bad part about the job was the 55-mile drive back to Marathon at the end of my shift, even when I brought a jerked chicken sandwich home to have for breakfast the next morning.
Working there was good for my fishing business as well. Word got around that a guide was working the door at Margaritaville and I scored a few charters on private boats out of Key West fishing for dorado and wahoo.
Summer moved into fall and the biggest celebration of the year in Key West, Fantasy Fest. If you want a deep dive on what it is, Google Fantasy Fest. It is essentially a score of days where people lose all of their inhibitions, wear as little as possible [or as fantastic as possible] and roam the streets with alcohol and lechery on their minds. Music flowed from every bar, restaurant and car window. It was loud, wild, and fun like Mardi Gras…just a lot warmer!
Working the door at Margaritaville was a lot more challenging during Fantasy Fest. I had to screen people for wearing too little [most of those people were happy and cool about it] and being too drunk [those people were mostly rude and belligerent]. I also had to throw people out of the bar for being nasty.
One guy, who was deaf, came into the bar and was trying to sell the “I am deaf, donate to help deaf people” cards while also caressing the butts of woman in the bar. I had to bend his arm behind his back to get him out of the bar and when he hit the street, he spit on me before running away. I was going to go after him, but a couple of cops yelled at me to let him go. Apparently, by Key West law if I had stepped away from the door taking the guy down would have been assault. I shrugged it off, toweled away the spit and continued to work.
A short time later, close to midnight, a small group of guys came staggering down the sidewalk drunker than skunks. The leader was a short guy in a University of Michigan jersey with a big feather mask on his face. He rolled up the door of Margaritaville and I had four or five inches on him. He eyed me up and down and drawled, “I’m coming in here.”
I smiled and shook my head. “Sorry pal, I think you’ve had too much to drink.”
He took a few steps away and got ready to push past me. As I blocked him the manager came to the door in a rush. “It’s OK, let him in!” he told me.
“But the guy is bombed!” I replied.
“I know him, let him in!”
I shrugged and stepped aside. The guy came up to me and lifted the mask. It was Jimmy Buffet. He smiled and clapped me on the arm “You’re doing a good job!” he said and went on in with his friends.
After that he would come in occasionally with his family to eat and I saw him play there a few times. That December fishing picked back up and I had no more time to work down there. I missed by coworkers and the Duval people, but the fishing was good and working 5AM to 6PM left no time for much anything else but sleep.
Looking back, I realize how fortunate I was to have experiences like this. Margaritaville is now an international power brand and it’s cool to have played a tiny little part in the story of the very first one.