The Number Ones

The Number Ones: Nancy Sinatra’s “These Boots Are Made For Walkin'”

In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.

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Nancy Sinatra – “These Boots Were Made For Walkin'”

HIT #1: February 26, 1966

STAYED AT #1: 1 week

Every once in a while in pop music, a sharp, versatile young singer joins forces with a spaced-out visionary producer, and we get a few warped and gooey and beautiful pop classics out of it. Whenever that happens, there’s this idea that the singer is the vehicle for the producer’s ideas, but that idea never gives enough credit to the singer. Instead, there’s usually some deeper level of collaboration at work — two disparate voices pushing each other in different directions, arriving somewhere nobody had ever been. It happened in the late ’90s with Aaliyah and Timbaland. It happened in the late ’70s with Donna Summer and Giorgio Moroder. And it happened in the mid ’60s with Nancy Sinatra and Lee Hazlewood.

Sinatra was, of course, show business royalty from birth. Her father Frank had sung the song “Nancy (With The Laughing Face)” about her in 1945, when she was five years old. But by 1966, a 25-year-old Sinatra had been languishing for a while, living the sort of half-stifled artistic life that lots of superstars’ kids seem to live. She’d dropped out of college, acted in a few B-movies, and been married to and divorced from the late-’50s teen idol Tommy Sands. She’d been recording for Reprise, her father’s label, since 1961, and a few of her songs had hit in Europe and Japan. But at home, she was hitless. She needed something.

Hazlewood, 11 years older than Sinatra, had been kicking around the periphery of the music business for years, developing an aesthetic that nobody has ever quite matched. It took time, but he eventually found his way into a mutant strain of mythic, psychedelic country music — one that, at least for a while, was weirdly compatible with the pop music of his day. He’d served in the Army during the Korean War, where he worked as a DJ on Armed Forces radio. After that, he teamed up with instrumental rockers Sanford Clark and Duane Eddy, co-writing and producing Eddy’s hits like “Rebel-Rouser” and “(Dance With The) Guitar Man.”

Even on those early tracks, Hazlewood figured out how to conjure atmosphere through spareness, communicating a whole lot with a deeply twangy guitar line. In 1965, Dino, Desi & Billy, a trio that featured the songs of Dean Martin and Desi Arnaz, had a hit with “I’m A Fool,” a ridiculously catchy song that Hazlewood wrote and produced. Around the same time, Dean Martin had a hit of his own with a version of “Houston,” which Hazlewood had written for Sanford Clark. Lee Hazlewood had entered the Rat Pack’s orbit.

The Reprise A&R head Jimmy Bowen matched Hazlewood up with Nancy Sinatra, and one afternoon, Hazlewood and the arranger Billy Strange played Sinatra some songs at her house. She liked “These Boots Are Made For Walkin'” as soon as she heard the bassline. Hazlewood had written the song for himself, and he intended to record it, but Sinatra convinced him to give her the song. Years later, she claims that she, quite rightly, told Hazlewood that “Boots” was not a song for a man: “I told him that coming from a guy it was harsh and abusive, but was perfect for a little girl to sing.” When Hazlewood left, Frank Sinatra, who’d been reading the newspaper in the other room, told Nancy that the “Boots” song was the best one they’d played.

“These Boots Are Made For Walkin'” is a total pop-music miracle, an endlessly replayable evisceration of some asshole guy who’s been messin’ where he shouldn’t have been messin’. There’s no firepower in Sinatra’s vocal; she’s talking as much as she’s singing. But she’s got her father’s gift for timing and his ability to broadcast huge levels of personality through quick little asides. Nancy’s sneery “ha!” might be the best moment on a song that’s full of great moments. She sounds tough and playful and bored, all at once. She’s too cool to be properly pissed off at the guy who’s cheated. Instead, she’s having fun with him the way a cat has fun with a mouse. He’s barely worth her energy. The song works as a laconic seizure of power, a purred threat.

The arrangement, meanwhile, is so simple and intuitive that it’s almost hard to hear how weird it is. Sinatra and Strange recorded the song with the Wrecking Crew, of course, and all the musicians play with the sort of confidence that can only come from playing on a huge percentage of the era’s hits. That descending bassline, right after Sinatra sings the chorus, is joining in the mockery, while the twangy acoustic guitar adds to the strut. But my favorite part is the horn arrangement, which keeps shifting throughout the song — quiet during the first verse, minimal Southern-soul fanfares during the second, big riffs during the third, a joyously stabby explosion on the fade-out. The end of the song is where Sinatra stops sing to the guy and instead talks to the boots, like they were people: “Are ya ready, boots? Start walkin’!” And the horns become the boots, going into hard-strut mode. I fucking love it. I love everything about it.

Over the next few years, Sinatra and Hazlewood kept recording together, finding this glorious form of hybridized drug-pop. “Some Velvet Morning” and “Sand” and “Bang Bang (My Baby Shot Me Down)” are all dizzy, head-blown masterpieces. Eventually, Hazlewood moved to Sweden and recorded a bunch of unheard solo albums that later became cult favorites, while Sinatra kept recording and acting and showing up in unexpected places: posing for Playboy in 1995, when she was 54, or collaborating with Morrissey and Jarvis Cocker and Sonic Youth in 2004. Both of them had amazing careers, but neither of them ever recaptured the slick, breezy glory of “These Boots Are Made For Walkin'” again. To their enormous credit, neither of them even seemed that interested in trying.

GRADE: 10/10

BONUS BEATS: Megadeth covered “These Boots Are Made For Walkin'” on their 1985 debut album Killing Is My Business… And Business Is Good, though they eventually took the cover off of later pressings of the record when Lee Hazlewood complained that their cover was a “perversion of the original.” Here’s Megadeth’s cover:

BONUS BONUS BEATS: Here’s “One Of These Days,” the quasi-cover of “These Boots Are Made For Walkin'” that Berkeley ska-punk originators Operation Ivy recorded in 1989:

BONUS BONUS BONUS BEATS: Here’s the infamous “love you long time” scene from Stanley Kubrick’s 1987 movie Full Metal Jacket, which is set to “These Boots Are Made For Walkin’,” and which thus creates a six-degrees connection between Frank Sinatra and 2 Live Crew: