Sinatra’s  influence can be heard everywhere from Angel Olsen to Lana Del Rey. This new compilation offers one of the only overarching retrospectives of a singular career.

Nancy Sinatra was both blessed and burdened with that last name. When she launched a pop career in the early 1960s, the Sinatra name immediately distinguished her from so many other promising young singers, and it meant she had a trusted adviser who could provide wise counsel (such as always own your masters). On the other hand, she was always Frank’s daughter in the public eye, always Nancy with the laughing face. She covered his songs, signed with his label (Reprise Records), and even made movies for his production company. It was her father who set up a meeting between her and Lee Hazlewood, who until then was best known for working with guitarist Duane Eddy in the 1950s. Both men have long been viewed as motivating figures in her career, barely behind the scenes, and it appears to be an ongoing struggle: “I can’t seem to get out of this trap,” she told The Believer in 2014. “I’m either Frank’s daughter or the person who sang with Lee Hazlewood. That’s OK; I don’t begrudge the men in my life. They helped me tremendously.” 

In many ways, her career and legacy have been defined by getting out of the shadows of these famous men and fighting to get her proper due as an artist. Sinatra has enjoyed few major reissues. There have been many greatest-hits collections, but few that do more than scratch the surface or offer any kind of broad overarching vision. In fact, the most substantial retrospective, 2011’s Cherry Smiles: The Rare Singles, was released on her own Boots label. That paucity of compilations makes Start Walkin’ a necessary addition to her catalog and immediately the best place for a newcomer to jump into her catalog. While most compilations cover a relatively brief period in the late 1960s when she was enjoying a steady stream of hits and even filming television specials, this one extends that range well into the 1970s, concluding with her retirement in 1976. These 23 tracks cover a lot of ground musically and critically, tracing her massive hits in the mid 1960s and following her as she weathers professional upheavals and changing pop trends. 

Start Walkin’ does not, however, include Sinatra’s very first singles, when she was a teenager trying to find her voice. She calls it her “Nancy Nice Lady” period, when she worked with Annette Funicello’s producer and presented a squeaky-clean image. Even Sinatra doesn’t think very highly of those songs, and Start Walkin’ locates her first sessions with Hazlewood in 1965 as the true start of her career. But that older material provides an interesting point against which to measure her transformation: She dyed her hair blonde, performed on TV in go-go boots and miniskirts straight from Mary Quant’s store in London. Always aware of the importance of visuals (her 1961 single “Cufflinks and a Tie Clip” was one of the first seven-inch singles packaged in a full-color sleeve), she projected power and sophistication from the stage and from the TV screen, along with a sexual confidence and emotional maturity that made her a stand-in for an entirely new generation of American women in the mid-’60s. Those boots suggested a whole army behind her. 

Those qualities extended to the music and then some. Hazlewood goaded her in a more sexual direction, often describing what he wanted in vulgar terms (in a 1968 interview with Cosmopolitan, Sinatra says he asked her to sing “like a 13- or 14-year-old girl who goes out with 40-year-old men”). But Sinatra’s songs never sound vulgar. Like the first generation of rock’n’rollers a decade earlier, Sinatra has a blast with innuendo rather than stating her desires outright. She teases the possibilities in her infamous cover of Cher’s “Bang Bang,” as though she knows that you know what she’s really singing about. That song was neither a single nor a hit at the time, but half a century later, it’s one of Sinatra’s most popular and enduring tunes largely because there are so many different layers in her performance: She foregrounds the poignancy in the lyrics—the sting of betrayal, the weight of regret—to match Billy Strange’s noir guitar licks. Similarly, she revels in the breezy ambiguity of “Sugar Town,” which may or may not be about turning on and tuning out. “I’m gonna lay right down here in the grass, and pretty soon all my troubles will pass,” she sings, her voice skipping along to the melody, but the song is less about the wink and more about the calm she finds looking up at the sky. 

As Start Walkin’ progresses through her career, the songs grow more florid and more idiosyncratic, incorporating folk rock, country, chamber pop, and a kind of theatrical pastoral psychedelia. Until he abruptly moved to Sweden (allegedly without telling Sinatra) and later after he’d returned to the States, Hazlewood served as her primary songwriter, and this compilation suggests that it was her versatility that allowed him to embrace his own mannerisms as a lyricist, producer, and pop conceptualist. The jump cuts on “Some Velvet Morning” are fairly well-known, but can still knock a listener off balance, while “Arkansas Coal (Suite)” is more cinematic and certainly more ambitious, as Sinatra sings in the voice of a woman whose life is made and then broken by the coal mines. More generally, her voice seems to invite oddball arrangement ideas, such as the backwards guitar solo on “Sand” or the solo kickdrum on “Lightning’s Girl,” which rumbles like an idling motorcycle. It’s fun listening to her navigate these unexpected flourishes, as though she is responding to the music and the music to her. 

One of the best moments on Start Walkin’—and certainly one I’ve returned to repeatedly—is a small, tossed-off line on “Friday’s Child.” The song, a hit in 1967, is about an individual abandoned by society, an outcast born with no blessings, only burdens. It seems to suggest some allegory, but Hazlewood’s lyrics can be vague. Still, Sinatra invests the song with the weight of experience and empathy, culminating in the line, “Friday’s child… whom they’ll forget to bury!” She spits the line, almost choking on her disgust. It’s the rare moment when Sinatra’s composure threatens to crack. But it never does, at least not on Start Walkin’, not even when she bursts into sobs at the end of her melodramatic reading of Dolly Parton’s “Down from Dover.”

It’s unfortunate that this retrospective concludes with “(L’été Indien) Indian Summer,” from 1976. Hazlewood takes lead, reciting in his stentorian baritone verses about an old lover and a beach and the moon, and Sinatra is reduced to singing wordlessly in the background—window dressing for his reminiscence. True, this was her final single before she retired to raise her daughters, but Start Walkin’ plays loose enough with the tracklist chronology. It has the perhaps unintended effect of leaving her career open-ended, as though she still hasn’t escaped the shadow of the men in her life. Everything up to that point proves otherwise. 


Buy: Rough Trade

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