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Other defining recordings include "Sugar Town", the 1967 number one "Somethin' Stupid" (a duet with her father), the title song from the James Bond film You Only Live Twice, several collaborations with Lee Hazlewood, and her cover of Cher's "Bang Bang (My Baby Shot Me Down)" (lyrics and music by Sonny Bono), which features during the opening sequence of Quentin Tarantino's Kill Bill.

Sinatra began her career as a singer and actress in the early 1960s, but initially achieved success only in Europe and Japan. In early 1966 she had a transatlantic number-one hit with "These Boots Are Made for Walkin'", which showed her provocative but good-natured style, and which popularized and made her synonymous with go-go boots. The promo clip featured a big-haired Sinatra and six young women in tight tops, go-go boots and mini-skirts. The song was written by Lee Hazlewood, who wrote and produced most of her hits and sang with her on several duets, including the critical and cult favorite "Some Velvet Morning". In 1966 and 1967, Sinatra charted with 13 titles, all of which featured Billy Strange as arranger and conductor.

Sinatra also had a brief acting career in the mid-60s including a co-starring role with Elvis Presley in the movie Speedway, and with Peter Fonda in The Wild Angels.