In 1966, Nancy Sinatra put herself on the radar by not only costarring in the outlaw biker film The Wild Angels but also releasing her debut solo album, Boots. Together, the movie and album helped Sinatra shape her image of a tough young woman divorced from her father Frank’s cocktail-swilling generation. Here, she opens with a symphonic pop rendition of The Rolling Stones’ “As Tears Go By” that’s crossed with Sergio Mendes–inspired bossa nova. Sinatra’s performance sounds more seductive and coy than the regal version sung by Marianne Faithful in 1964. Sinatra counters Stones with Beatles in the following go-go take on The Fab Four’s “Day Tripper.” Since Lee Hazlewood produced the album, it was inevitable for Sinatra to sing a few of his originals, but this proved a solid fit. His intricately arranged “I Move Around” plays like a much hipper Sonny & Cher song, while “So Long, Babe” is fittingly flippant. And of course the intimidating and catchy hit “These Boots Were Made for Walkin’” cemented a workable chemistry between the two.