Songs with Earlier Histories Than the Hit Version

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Gypsy Woman

First recorded by The Impressions (US #20/R&B #1 1961).
Other hit versions by Brian Hyland (US #3/UK #42 1970), Santana (US #31 1990).

From the wiki: “‘Gypsy Woman’ was written by Curtis Mayfield and was first recorded by his group The Impressions, the group’s first single following the departure of lead singer Jerry Butler. The recording reached #2 on the R&B chart and #20 on the Billboard Hot 100 in 1961.

“In 1970, Brian Hyland recorded a successful Del Shannon-produced cover version which peaked at #3 on the Hot 100. Santana also covered ‘Gypsy Woman’, in 1990 when its promotional single peaked at #31 on the Hot 100.”

Brian Hyland, “Gypsy Woman” (1970):

Santana, “Gypsy Woman” (1990):