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During this time, Milsap worked as a session musician on numerous projects including two songs with Elvis Presley: "Don't Cry Daddy" in 1969 and "Kentucky Rain" in 1970.
His second cousin on his maternal Irish side was Eddie Rabbitt, the Nashville country music star whose song "Kentucky Rain" was a hit for Elvis Presley and whose song "Every Which Way But Loose" was the theme tune for a film starring Clint Eastwood and an orangutan.