In 1986, I worked as a waiter in Bennigans that had one Mickey Mouse stay home and listen to Jimmy Buffett shirt of those 3-hour continuous music tape loops, so I would generally hear the same songs repeated over and over after a few shifts. Basically, the music was just above the background level. I would imagine that some focus groups or experts figured out how to put together an innocuous loop that had the greatest possible appeal. Buffett and The Eagles were all over that loop with Margaritaville, Come Monday, and Cheeseburger all being perfect songs to sit at a bar and devour a plate of hot wings or drink the more expensive frozen drinks. If you went to Fridays or any other restaurant like that in the mid-80s, it would be a very similar song loop. if you went to any beach bar during the 80s, there would be the same type of songs playing in the background.
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If you got lucky in some regular bar or drinking Mickey Mouse stay home and listen to Jimmy Buffett shirt establishment of that era, Buffett probably was in the rotation. During this same era, the cheapo Caribbean vacation became popular with Club Med, and the various all-inclusive junkets taking off. At these places, a steady diet of beach music including Bob Marley and Buffet played incessantly. Accordingly, if you went down with your friends to some spot in Jamaica during the 80s, early 90s, you heard your share of Jimmy Buffet; and you obviously would have heard Jimmy Buffett in Key West or any of the Southern US vacation spots. You would hear it if you went on any Spring Break trip in FL, not in the clubs; but in every bar where you’d pre-game or do real drinking.