How do these grab you, darlin’? Nancy Sinatra’s 20 best songs – ranked!

Sixty years after the release of her debut album, Boots, we celebrate her finest tracks – from Bond themes to LSD anthems

20. The Last of the Secret Agents? (1966)

Before she sang a Bond theme, Nancy Sinatra had recorded a parody of one: twanging guitar, John-Barry-mocking brass and all. The great lyrics – “He’s never caught a spy I’m told / He’s never even caught a cold” – mean preposterous mid-60s novelty records come no better.

19. Don’t Let Him Waste Your Time (2004)

Sinatra’s eponymous 2004 album gained attention for the involvement of Morrissey, but his Let Me Kiss You sounds jarringly weird sung by her. A version of Jarvis Cocker’s Don’t Let Him Waste Your Time suits Sinatra better, the sassy voice of These Boots Are Made for Walkin’ grown older and wiser, dispensing kick-him-out relationship advice.

18. Life’s a Trippy Thing (1971)

When it comes to Sinatra’s duets with Dad, Somethin’ Stupid gets all the plaudits, but this bizarre slice of swinging cod-hippy whimsy – presumably intended to suggest Frank Sinatra had a passing knowledge of the counterculture – is far more intriguing, not least for the sound of him singing: “Hello, birdies! Hello, spring!”

17. I’ve Been Down So Long (It Looks Like Up to Me) (1968)

There are, essentially, two kinds of duet between Sinatra and Lee Hazlewood: the weirdly erotic ones; and the ones where Hazlewood plays a loser and Sinatra his long-suffering partner. Been Down So Long is a great spin on the second variety. Sinatra enumerates Hazlewood’s woes; he agrees; then she reveals herself as their source, offering fabulously sarky consolation: “Poor Lee.”

16. Kinky Love (1976)

Sinatra was always great at sexy-but-tongue-in-cheek. She struggled commercially in the 70s – a symbol of the 60s trying to find her footing in a different decade – but Kinky Love was unfairly overlooked. A gorgeous 1991 cover by the shoegazers Pale Saints unexpectedly enjoyed a burst of 21st-century TikTok virality.

15. Lightning’s Girl (1967)

A distant relative, emotionally speaking, of the Angels’ girl group classic My Boyfriend’s Back, Lightning’s Girl recast the wisecracking swagger of These Boots in more dramatic surroundings: fuzzed-out garage-rock bass, an ominous bass drum thud, hair-raising bursts of Psycho-soundtrack strings, Sinatra muttering menacing asides.

14. Down from Dover (1972)

Dolly Parton’s saga of unmarried motherhood really works as a Nancy and Lee duet. The story is subtly different: playing the baby’s father, Hazlewood insists he’s trying to do the right thing, but his vocal is too ambiguous for the listener to believe him. Sinatra, meanwhile, is filled with foreboding. It doesn’t end well.

13. Drummer Man (1969)

Drummer Man wasn’t a hit, but it should have been. With lyrics about the drudgery of life as a musician’s wife, it has an unexpectedly funky backing that carries a faint hint of Donovan’s then-recent hit with Jeff Beck, Barabajagal (Love Is Hot) – it’s amazing that the rhythm track never became a sampler’s staple.

12. How Does That Grab You, Darlin’? (1966)

On the one hand, this was a craven attempt to follow up These Boots with more of the same: similar rhythm, similar hook, similar brass arrangement. On the other, Sinatra gives it everything and her performance is fantastic: “You smart alec tomcat, you!” Who could resist?

11. Jackson (1967)

It requires chutzpah to take on a duet months after Johnny Cash and June Carter have scored a hit with it, but Nancy and Lee’s version of Jackson’s marital discord saga amps up the camp quotient to fabulous effect. Hazlewood’s mordant delivery suggests he knows things are going to turn out badly, despite his protestations.

10. So Long, Babe (1966)

Sinatra’s first single written by Hazlewood wasn’t a hit, but it was a vast improvement on the limp bubblegum she had spent the previous five years recording. It was hipper – with a hint of folk-rock in its sound – and tougher. He’s leaving, she doesn’t seem bothered; to be honest, he sounds like a liability.

9. I Move Around (1966)

Sinatra’s albums are a mixed bag in terms of quality, but there is the occasional gem. From her debut, Boots, the Hazlewood-penned I Move Around offers a glitzy travelogue – Zanzibar! Paris! Singapore! London! – underscored with melancholy, the jet-setting inspired by a broken heart: “Since I saw you with her – yeah, I move around.”

8. Friday’s Child (1967)

Something of a curveball after the salty but lighthearted These Boots and How Does That Grab You, Darlin’?, Friday’s Child offered emotionally fraught melodrama, raw-throated vocals, blues-style guitar, powerful strings and unmitigated lyrical despair. Hard luck is her brother! Her sister is misery!

7. Sand (1966)

From her second album, How Does That Grab You?, the first Nancy and Lee duet introduced a different Sinatra: less sassy trash-talker, more shadowy siren (“oh taste these lips, sir, if you can”) invariably capable of reducing Hazlewood’s hard-bitten wanderin’ man to a lust-racked wreck. It’s also brilliantly arranged: shimmering Autoharp, backwards guitar.

6. Sundown, Sundown (1968)

You get a touch more Lee than Nancy, but she gets the best moment in the song – the staccato: “Come on, come on, come on, come on back to me,” at the end of the chorus. And what a tune this is: atmospheric, thrilling, emotionally intense; an epic condensed into 162 seconds.

5. Sugar Town (1966)

An inveterate mischief-maker, Hazlewood wasn’t a drug user, but nevertheless wrote a song about the joys of LSD, gave the track to Frank Sinatra’s daughter – an improbable acid proselyte – then watched it reach No 1 on the easy listening chart. One suspects this was due more to the delightful tune than Sugar Town’s sentiment.

4. You Only Live Twice (1967)

Sinatra was a distinct pivot away from the style of the previous Bond theme singers, Tom Jones and Shirley Bassey. Lucky enough to get one of the best Bond themes, she was also smart enough to re-record the single version in noticeably more voguish style, with Hazlewood producing and Billy Strange arranging.

3. Summer Wine (1966)

Bafflingly relegated to a B-side, this is the quintessential Nancy and Lee duet. Dramatic, slightly hallucinatory and blessed with a wonderful tune, it involves a mysterious traveller and an even more mysterious femme fatale. This time, she robs him blind, but – of course – he would happily come back for more. Marvellous.

2. These Boots Are Made for Walkin’ (1965)

Why did These Boots finally turn Sinatra into a star? It’s a killer song, superbly produced, landing somewhere between garage-esque folk rock, the tougher end of the girl group spectrum and easy listening. But, ultimately, it’s her performance: she sings it like it’s the song she has been waiting for, which of course it was.

1. Some Velvet Morning (1967)

As anyone familiar with his solo oeuvre knows, Hazlewood was an innately strange writer. Some Velvet Morning was the moment in Sinatra’s career when he gave his weirdness full flight. No one, including its author, has come up with a convincing explanation of what it’s about, or who Sinatra’s character, Phaedra, is meant to be. Ethereal spirit? Alluring hippy maiden? Something more sinister? Beyond its enigmatic qualities, its enduring appeal lies in what an incredible song it is: beautiful but unsettling, fabulously arranged, with a shifting time signature. Whatever her role is, Sinatra plays it perfectly.