Lee Hazlewood Wanted Nancy Sinatra To Sing ‘Boots’ In A Jailbait Style

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Though her dad was Frank Sinatra, the man who really shaped Nancy Sinatra into the iconic sex kitten of the ’60s was collaborator Lee Hazlewood. When it came time to record the song that would define her career, Hazlewood wasn’t satisfied with her vocal. In her autobiography, Nancy recalled that Hazlewood instructed her to sing like “a 14-year-old girl in love with a 40-year-old man.” They tried the song again, and the freshly-divorced Sinatra still wasn’t giving it the vibe Hazlewood wanted. “I was still singing like Nancy NiceLady,” she recalled.