Nancy Sinatra's 20 Best Songs: A Definitive Ranking of Her Iconic Career
Sixty years after the release of her debut album, Boots, Nancy Sinatra remains a towering figure in pop and rock music. From Bond themes to psychedelic anthems, her discography is a rich tapestry of innovation and style. In this expanded celebration, we rank her 20 finest tracks, delving into the stories behind each song and their lasting impact.
20. The Last of the Secret Agents? (1966)
Before she sang a Bond theme, Nancy Sinatra recorded this brilliant parody, complete with twanging guitar and brass that mock John Barry's iconic 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, showcasing her playful wit.
19. Don't Let Him Waste Your Time (2004)
Her 2004 self-titled album gained attention for Morrissey's involvement, but it was Jarvis Cocker's Don't Let Him Waste Your Time that truly suited Sinatra. With a voice grown wiser from her These Boots Are Made for Walkin' days, she delivers sassy, kick-him-out relationship advice with timeless appeal.
18. Life's a Trippy Thing (1971)
While duets with her father Frank Sinatra often highlight Somethin' Stupid, this bizarre slice of swinging cod-hippy whimsy is far more intriguing. It attempts to suggest Frank had knowledge of the counterculture, featuring him singing "Hello, birdies! Hello, spring!" in a uniquely captivating moment.
17. I've Been Down So Long (It Looks Like Up to Me) (1968)
This duet with Lee Hazlewood exemplifies their dynamic where Hazlewood plays a loser and Sinatra his long-suffering partner. Sinatra enumerates his woes, he agrees, and she reveals herself as their source, offering fabulously sarky consolation with "Poor Lee."
16. Kinky Love (1976)
Sinatra struggled commercially in the 70s but Kinky Love was unfairly overlooked. A gorgeous track, it later gained unexpected 21st-century virality on TikTok after a 1991 cover by shoegazers Pale Saints, highlighting its enduring sexy-but-tongue-in-cheek charm.
15. Lightning's Girl (1967)
Emotionally akin to the Angels' My Boyfriend's Back, this song recasts the swagger of These Boots in dramatic garage-rock surroundings. With fuzzed-out bass, ominous drums, and Psycho-soundtrack strings, Sinatra mutters menacing asides that add to its intense atmosphere.
14. Down from Dover (1972)
As a Nancy and Lee duet, Dolly Parton's saga of unmarried motherhood takes on new depth. Hazlewood plays the ambiguous father, while Sinatra fills the role with foreboding, creating a subtly different and emotionally charged narrative that doesn't end well.
13. Drummer Man (1969)
Though not a hit, Drummer Man should have been. With lyrics about a musician's wife's drudgery, it features an unexpectedly funky backing reminiscent of Donovan's Barabajagal, making it a missed opportunity for sampler's staples.
12. How Does That Grab You, Darlin'? (1966)
A follow-up to These Boots, this track mimics its rhythm and brass but stands out due to Sinatra's fantastic performance. Her delivery of lines like "You smart alec tomcat, you!" is irresistible, showcasing her charismatic energy.
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 a layer of fabulous drama to this saga of marital discord.
10. So Long, Babe (1966)
Sinatra's first Hazlewood-written single marked a vast improvement from her earlier bubblegum tracks. Hipper with a folk-rock hint, it features a tough attitude as he leaves and she remains unbothered, painting him as a liability.
9. I Move Around (1966)
From her debut album Boots, this Hazlewood-penned gem offers a glitzy travelogue to places like Zanzibar and Paris, 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, this track delivers emotionally fraught melodrama with raw-throated vocals, blues-style guitar, and powerful strings. Its lyrical despair, declaring hard luck as her brother and misery as her sister, is unmitigated and gripping.
7. Sand (1966)
The first Nancy and Lee duet introduces a shadowy siren Sinatra, capable of reducing Hazlewood's wanderin' man to a lust-racked wreck. Brilliantly arranged with shimmering Autoharp and backwards guitar, it's a standout from her second album.
6. Sundown, Sundown (1968)
Though featuring more Lee, Sinatra gets the best moment with her staccato "Come on, come on, come on, come on back to me." This atmospheric, thrilling tune condenses epic emotion into 162 seconds.
5. Sugar Town (1966)
Hazlewood, an inveterate mischief-maker, wrote this LSD-themed song for Frank Sinatra's daughter, watching it reach No 1 on the easy listening chart. Its delightful tune likely contributed more to its success than its psychedelic sentiment.
4. You Only Live Twice (1967)
Sinatra pivoted from previous Bond singers like Tom Jones and Shirley Bassey. Smart enough to re-record in voguish style with Hazlewood producing, she delivered one of the best Bond themes, showcasing her adaptability and flair.
3. Summer Wine (1966)
Bafflingly a B-side, this quintessential Nancy and Lee duet is dramatic and hallucinatory. It involves a mysterious traveller and a femme fatale who robs him blind, yet he'd return for more, making it a marvellous track.
2. These Boots Are Made for Walkin' (1965)
This killer song, superbly produced, blends garage-esque folk rock, girl group toughness, and easy listening. Sinatra's performance, singing it like the song she'd been waiting for, ultimately made it a star-making hit.
1. Some Velvet Morning (1967)
Hazlewood's weirdness takes full flight in this enigmatic track. No convincing explanation exists for its meaning or Sinatra's character Phaedra, but its beauty, unsettling arrangement, and shifting time signature make it an incredible song, played perfectly by Sinatra.
Nancy Sinatra's career is a testament to her versatility and enduring appeal, with these 20 songs highlighting her finest moments across decades of music.
