183) Nancy Sinatra & Frank Sinatra – “Somethin’ Stupid”

When Sinatra founded Reprise Records in 1960, one of the benefits of being Chairman of the Board was artistic freedom. Between his more standard offerings, he recorded a tribute to his onetime mentor, bandleader Tommy Dorsey (1962’s I Remember Tommy); paid homage to the late President John F. Kennedy with a collection of patriotic songs (1964’s America, I Hear You Singing); and revisited his pioneering ’50s concept albums with a rumination on aging (1965’s September of My Years). He also seized the opportunity to work with other high-profile talents he admired, cutting albums for the first time with Count Basie, Duke Ellington, and bossa nova luminary Antônio Carlos Jobim.

Nevertheless, Sinatra’s most famous collaboration of the ’60s wasn’t with an orchestra leader or a songwriter, but his daughter Nancy. After sessions wrapped for the 1967 album Francis Albert Sinatra & Antônio Carlos Jobim, Sinatra swapped out the Brazilian musician for the pop starlet, and bossa nova for tepid MOR. Nancy’s regular duet partner, Lee Hazlewood, manned the production boards alongside Jimmy Bowen, who had recorded “Strangers in the Night.” On the docket was a novelty duet called “Somethin’ Stupid,” which would allow the Sinatras to share their love of singing, and also sell twice as many records as they would separately.

“Somethin’ Stupid” had first appeared the year before as a duet between the song’s writer, C. Carson Parks (older brother of songwriter/arranger Van Dyke Parks) and his wife Gaile Foote. It’s a simple song about a man and a woman platonically enjoying each other’s company until one of them “spoil[s] it all by saying something stupid like ‘I love you.’” The twist is that, because both are singing the same words simultaneously, it isn’t clear which was the one to awkwardly blurt out their romantic feelings. Carson and Gaile’s winsome recording has some corny appeal, but it’s much too slight to be an obvious candidate for a huge international hit.

Frank and Nancy’s version retains the basic arrangement of the original, including the hushed unison, non-harmonizing vocals and a flourish of Spanish guitar. The one addition is a strings section so heavy-handed that the song’s fragile charms buckle beneath its weight. Similarly, while Carson and Gaile’s vocal styles were well matched, the Sinatras, despite their consanguinity, are less of a natural fit. In fact, “Somethin’ Stupid” barely even qualifies as a duet — that would imply some sort of equal footing between the two partners. Even in half-assed “Strangers in the Night” mode, Frank dominates the recording, relegating Nancy to little more than an anonymous background singer. True, Frank was the superstar with the once-in-a-generation voice, but Nancy was at least as popular as her old man in the mid-’60s, and had an appealing vocal style of her own, though you wouldn’t know it listening to this.

Jokers have long snickered at the oddity of a father and daughter singing a love song to each other, but any incestuous overtones would only threaten to make “Somethin’ Stupid” more interesting than it actually is. Instead, the dully non-committal vocal performances overcorrect for any possible hint of romance, contributing to the record’s overall stale, airless feel. The Sinatras don’t even sound like acquaintances, much less lovers, much less relatives.

More bothersome, though, is the record’s paternalistic bent. The inequality between the two singers comes off as Frank indulging Nancy in play-acting at his career, all the while ensuring that she (and rock and roll, and youth culture in general) knows her proper place. Father and daughter may record a song together, but it will be one that befits his sound and image, not hers, and one where he’s given the lead role. He’s not ceding co-billing to some flash in the pan, even if she happens to be his daughter.

Despite Nancy’s minimal role and the song’s questionable themes, “Somethin’ Stupid” united the Sinatras’ fan bases, topping both the Hot 100 and the easy listening charts. But while the song became one of the biggest hits of 1967, it was also somewhat of a dead end. Frank would never again have a Top 20 pop single; even signature tunes like 1969’s “My Way” and 1980’s “Theme from New York, New York” were only middling chart successes. Nancy would briefly have better luck before making her last-ever trip into the Top 40 with the Hazlewood duet “Some Velvet Morning” in early 1968.

The Sinatras recorded two more duets, 1970’s “Feelin’ Kinda Sunday” and 1971’s “Life is a Trippy Thing,” but neither troubled the charts. Father and daughter would both return to duets with other partners over the course of their career. Nancy continued collaborating with Hazlewood into the ’70s (reuniting for Nancy & Lee 3 in 2004), then recorded a moderately successful country album with Mel Tillis in 1981. In the ’90s, Frank issued a pair of blockbuster albums, 1993’s Duets and 1994’s Duets II, in which he shared the mic with a series of younger singers. Notably, Frank insisted on recording his share of the duets alone, then sending them off for his partners to follow his lead. Much as with “Somethin’ Stupid” decades earlier, Frank made sure he was always the star of the duet. 3

Hit #1 on April 15, 1967; total of 4 weeks at #1
183 of 1062 #1’s reviewed; 17.23% through the Hot 100

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155) Nancy Sinatra – “These Boots are Made for Walkin'”

It would be neat symmetry to think of “These Boots are Made for Walkin’” as a rebuke to the previous number-one’s questionable sexual politics. But even if there had been a gap between the two records’ releases, you get the sense that “Boots” would’ve been too cool to pay that melodramatic throwback any attention. Whereas the conventional gender attitudes and Four Seasons-esque falsetto leaps of “Lightnin’ Strikes” fit squarely within the mold of early ’60s pop (even as its weirdness elevates it to some other dimension), Nancy Sinatra’s self-assured sexiness and tart, plainspoken vocals epitomized the increasing directness of the latter half of the decade. Even the fact that she was singing about boots – rugged men’s footwear co-opted as ultra-mod women’s fashion, both covering legs and emphasizing their form – felt hip and transgressive.

The tension between the masculine and the feminine recurs throughout Sinatra’s ’60s discography, particularly in her collaborations with songwriter/producer Lee Hazlewood. Their duets emphasize the gender divide by casting them as extreme archetypes: him, the hard-bitten rambler; her, the dewy-eyed siren. (The 1967 single “Some Velvet Morning” even fluctuates between time signatures depending on who’s singing.) On “Boots,” though, Sinatra is left to inhabit both roles by herself. By wedding her girlish purr to Hazlewood’s terse, tough-guy phrasing, Sinatra both confirms and subverts conventional expectations of femininity, turning “Boots” into a cross between a come-on and a threat.

Any hint of danger in the record, however, is mostly defused by its sense of humor, from the childlike vernacular (“truthin’,” “samin’”), to the flamboyantly upbeat horns, to Chuck Berghofer’s heat-warped doublebass slide, at once foreboding and absurd. Even Sinatra’s warning that “one of these days, these boots are gonna walk all over you” is delivered with a wink. Is this playfulness meant to assure listeners that her forwardness is just role-playing, that they don’t have to take her seriously? Or is the song tripling back on itself, smuggling in a pro-feminist message in the guise of just kidding? (Sinatra’s wry delivery does suggest she’s telling a joke to someone who’s not getting it, and relishing the thought of how hard the punchline will land once he does.) Perhaps “Boots” and “Lightnin’ Strikes” aren’t so different after all. In an era where traditional gender roles were being questioned, both songs offer ambiguous answers, muddying the waters between what’s intended to be ironic and what’s just camp. 8

Hit #1 on February 26, 1966; total of 1 week at #1
155 of 1016 #1’s reviewed; 15.26% through the Hot 100