As Musicholics notes, back in 1979, Rupert Holmes was working on his fifth album, and he and his backup musicians eventually came up with a melody punctuated by an unorthodox drum beat -– Holmes called it “upside down Reggae.” He and his crew then painstakingly cut the tape with a razor (this was decades before the process could be done digitally) and eventually had a “loop” that formed the musical foundation for an as-yet-unwritten song.
As Songfacts explains, Holmes tried to pin a variety of lyrics to the melody, without success, before taking inspiration from the personal ads. He began imagining himself in the position of a person who was compelled to take out such an ad. Eventually, Holmes hit on a lyric: “If you like Humphrey Bogart and getting caught in the rain.”
He was just about to sing it to his band before he decided, on the spot, that the Bogart reference wasn’t right. Instead, he thought about the first thing a couple on a romantic escape would do, and he decided they’d drink a tropical adult beverage. The words “pina colada” had the right meter, and the rest, as they say, is history. “I had never had a piña colada in my entire life,” Holmes admitted.
