Nancy Sinatra's 20 Greatest Songs: A Definitive Ranking from Boots to Bond
Sixty years after the release of her groundbreaking debut album Boots, Nancy Sinatra remains an enduring icon of 1960s pop culture. To mark this milestone, we present a definitive ranking of her 20 finest tracks, spanning from Bond themes to psychedelic anthems and unforgettable duets.
20. The Last of the Secret Agents? (1966)
Before she lent her voice to a James Bond theme, Nancy Sinatra recorded this brilliant parody. Featuring twanging guitars and brass that mock John Barry's style, the lyrics—"He’s never caught a spy I’m told / He’s never even caught a cold"—make it a standout among mid-60s novelty records.
19. Don’t Let Him Waste Your Time (2004)
Her 2004 self-titled album gained attention for Morrissey's involvement, but it's Jarvis Cocker's Don’t Let Him Waste Your Time that truly shines. Sinatra's voice, matured from her These Boots Are Made for Walkin’ days, delivers sassy, kick-him-out relationship advice with wisdom.
18. Life’s a Trippy Thing (1971)
While Somethin’ Stupid with Frank Sinatra gets the plaudits, this bizarre slice of swinging cod-hippy whimsy is far more intriguing. It features Frank singing "Hello, birdies! Hello, spring!", offering a curious glimpse into the counterculture.
17. I’ve Been Down So Long (It Looks Like Up to Me) (1968)
A standout duet with Lee Hazlewood, this track showcases Sinatra enumerating Hazlewood's woes before revealing herself as their source. Her fabulously sarky consolation—"Poor Lee"—adds a layer of dark humor.
16. Kinky Love (1976)
Sinatra struggled commercially in the 70s, but Kinky Love was unfairly overlooked. This sexy-but-tongue-in-cheek track later gained unexpected virality in the 21st century through a cover by shoegazers Pale Saints on TikTok.
15. Lightning’s Girl (1967)
Emotionally akin to the Angels' My Boyfriend’s Back, this track recasts the swagger of These Boots in dramatic surroundings. With fuzzed-out garage-rock bass, ominous drums, and Psycho-soundtrack strings, Sinatra mutters menacing asides that captivate.
14. Down from Dover (1972)
A Nancy and Lee duet of Dolly Parton's saga of unmarried motherhood, this version subtly shifts the story. Hazlewood's ambiguous vocal as the baby's father contrasts with Sinatra's foreboding, creating a tense narrative that doesn't end well.
13. Drummer Man (1969)
Though not a hit, Drummer Man deserved to be. With lyrics about the drudgery of a musician's wife, it features an unexpectedly funky backing reminiscent of Donovan's Barabajagal, making it a missed opportunity for samplers.
12. How Does That Grab You, Darlin’? (1966)
A follow-up to These Boots with a similar rhythm and brass arrangement, this track succeeds due to Sinatra's fantastic performance. Her delivery of lines like "You smart alec tomcat, you!" is irresistible.
11. Jackson (1967)
Months after Johnny Cash and June Carter's hit, Nancy and Lee's version amps up the camp quotient. Hazlewood's mordant delivery suggests impending doom, adding depth to this saga of marital discord.
10. So Long, Babe (1966)
Sinatra's first single written by Hazlewood marked a vast improvement from her earlier bubblegum pop. With a hint of folk-rock and a tougher edge, it depicts a breakup where she seems unbothered by his departure.
9. I Move Around (1966)
From her debut album Boots, this Hazlewood-penned track offers a glitzy travelogue—Zanzibar, Paris, Singapore, London—underscored with melancholy from a broken heart: "Since I saw you with her – yeah, I move around."
8. Friday’s Child (1967)
A curveball after lighter hits, Friday’s Child delivers emotionally fraught melodrama. With raw-throated vocals, blues-style guitar, and powerful strings, it paints a picture of despair: "Hard luck is her brother! Her sister is misery!"
7. Sand (1966)
The first Nancy and Lee duet introduced a different Sinatra: a shadowy siren capable of reducing Hazlewood's wanderin’ man to a lust-racked wreck. Brilliantly arranged with shimmering Autoharp and backwards guitar, it's a standout.
6. Sundown, Sundown (1968)
Though featuring more Lee than Nancy, Sinatra gets the best moment with the staccato "Come on, come on, come on, come on back to me." This atmospheric, thrilling track condenses an epic into 162 seconds.
5. Sugar Town (1966)
Hazlewood, an inveterate mischief-maker, wrote this song about the joys of LSD and gave it to Frank Sinatra's daughter. It reached No. 1 on the easy listening chart, likely due to its delightful tune rather than its psychedelic sentiment.
4. You Only Live Twice (1967)
Sinatra pivoted from previous Bond theme singers like Tom Jones and Shirley Bassey. Smart enough to re-record in a more voguish style with Hazlewood producing, she delivered one of the best Bond themes ever.
3. Summer Wine (1966)
Bafflingly relegated to a B-side, this is the quintessential Nancy and Lee duet. Dramatic and slightly hallucinatory, it involves a mysterious traveller and a femme fatale who robs him blind—yet he'd happily return for more.
2. These Boots Are Made for Walkin’ (1965)
This killer song, superbly produced, blends garage-esque folk rock, girl group toughness, and easy listening. Ultimately, it's Sinatra's performance—singing it like the song she'd been waiting for—that made it a star-making hit.
1. Some Velvet Morning (1967)
The moment Hazlewood's weirdness took full flight, this track remains enigmatic. No convincing explanation exists for its meaning or Sinatra's character, Phaedra. Beautiful but unsettling, with a shifting time signature and fabulous arrangement, it's an incredible song played perfectly by Sinatra.
From her debut to her enduring legacy, Nancy Sinatra's music continues to captivate, blending sass, mystery, and timeless appeal. This ranking celebrates the depth and diversity of her iconic career.
