Traditionally, the fall is a time of transition – a bridge between the sunny skies of summer and the icy grip of winter. However, this singular season has elusive qualities of its own. It may be darker and cooler, but as this selection of enduring autumnal classics proves, plenty of equally cool songs have been inspired by its shifting landscapes and ever-changing moods.
The Cranberries: Linger
Even though the coming of the fall signifies the daylight hours getting shorter, it’s a season rife with beauty, with warm sunlight often providing a golden glow in the evening. Indeed, the fall has a lot in common with The Cranberries’ debut US Top 10 hit from 1994 in that it’s a romantic, beguiling time of year and – like then song’s title – most people hope it will “Linger” long and help keep the advance of winter at bay.
Bombay Bicycle Club: Autumn
An absorbing deep cut from the London indie outfit’s debut album, I Had The Blues, But I Shook Them Loose, “Autumn” doesn’t specifically refer to the season anywhere in its lyric. Nonetheless, the song is appropriately titled, for its restless psych-tinged backdrop ebbs and swells in an adventurous fashion across its four-minute timespan and it captures the fall’s ever-changing moods to a T.
Florence + The Machine: My Boy Builds Coffins
Florence Welch has revealed she founded a witches’ coven and possessed books of spells when she was at school, so it’s logical enough to imagine her writing a song with Halloween-esque tendencies such as “My Boy Builds Coffins.” However, while this dramatic, yet highly accessible pop song from her band’s 2009 debut Lungs feels right at home in a list of songs suitable for the fall, its inspiration was entirely literal. Welch’s boyfriend of time did actually make coffins – hence the gallows humor in the lyric: “He’s made one for himself, one for me too/One of these days he’ll make one for you.”
Mazzy Star: Fade Into You
Imbued with loss and longing and topped off with one of Hope Sandoval’s most laconic vocals, Mazzy Star’s signature hit “Fade Into You” never truly goes out of fashion – and it continues to endure thanks to placings in TV series such as Yellowjackets and Netflix’s Virgin River. Though theoretically a song for all seasons, this somnolent alt-rock classic is suffused with a warm glow of melancholy which feels like the very epitome of the fall.
Lord Huron: Harvest Moon
Lord Huron celebrated the U.S. Top 10 success of 2018’s Vide Noir by recording two well-received Spotify Singles, one of which saw the L.A.-based alt-rock outfit saluting Neil Young with a cover of the Canadian-American singer-songwriter’s 1992 hit “Harvest Moon.” Though adding vibes, pedal steel and additional layers of twang, Lord Huron’s take of the song is still remarkably faithful and it perfectly portrays the promise of a clear fall night when “there’s a full moon on the rise/so let’s go dancing in the light.”
Jay & The Techniques: Apple, Peaches, Pumpkin Pie
Due to the autumnal flavor of its title’s contents, Jay & The Techniques’ “Apple, Peaches, Pumpkin Pie” is a welcome feature of many a Halloween playlist. In reality, though, the Pennsylvanian outfit’s signature hit tastes good any time. A brassy and infectious soul-infused pop hit, it cracked the U.S. Top 10 on release in 1967, but enjoyed further success when Mercury belatedly released it in the U.K. and it became a staple of Britain’s Northern soul scene during the early 70s.
Amy Winehouse: October Song
One of numerous highlights from Amy Winehouse’s precocious debut Frank, “October Song” isn’t specifically about the fall, but it’s tied to the season as the lyric relates to the October death of the late singer’s pet canary, Ava – also a beautiful songbird who captured Amy’s heart during her all-too-brief lifetime. Despite this underlying sadness, “October Song” makes for a playful, life-affirming tribute with a Portishead-esque vibe, with Amy mourning her little bird’s loss, but also believing she’ll be “reborn like Sarah Vaughan.”
Billy Idol: Eyes Without A Face
His first brush with the U.S. Top 10, Billy Idol’s “Eyes Without A Face” featured a smooth, synth-based arrangement and his suave, Frank Sinatra-esque croon, but the song’s superficial beauty masked an ugliness worthy of Dorian Gray. Indeed, the song took its title from the controversial 1960 French horror movie of the same name and its premise – an unhinged surgeon attempting to restore his disfigured daughter’s face with features from murder victims – has more than a little of the macabre we usually associate with Halloween celebrations in late fall.
Lana Del Rey: Cinnamon Girl
Despite its title, this Cinnamon Girl isn’t a cover of the Neil Young song of the same name, but it is one of many great tracks from Lana Del Rey’s acclaimed sixth album, Norman F_ing Rockwell. Sparse, tender and emotionally fraught, this beautiful, electro-tinged ballad captures that bittersweet moment as summer ends and the fall takes hold.
The Police: Every Breath You Take
Frequently misinterpreted, Sting’s Orwellian ode to surveillance, control and obsession, “Every Breath You Take” requires little introduction. As the biggest U.S. and U.K. hit of 1983, the double Grammy Award-winning song remains his former band’s high watermark and while it’s not specifically a seasonal song, its brooding musical backdrop possesses a distinctly autumnal chill.
Nat ‘King’ Cole: Autumn Leaves
The fall frequently provided inspiration for Nat ‘King’ Cole. In 1950, he recorded ‘’Tis Autumn” with his Nat ‘King’ Cole Trio, while his recording of “Orange Colored Sky” (with Stan Kenton’s Orchestra) peaked at No. 11 on Billboard’s Best Seller chart in September of the same year. However, Cole’s 1955 recording of “Autumn Leaves” (adapted from the French song “Les Feuilles Mort”) remains particularly striking. The inspiration for the 1956 film of the same name, the song features one of Cole’s most haunting vocals and a string arrangement that swirls like autumn leaves falling from the trees.
Noah Kahan: Stick Season
In New England, locals often refer to the fall (or more specifically the period after Halloween but before the winter snow begins) as the “Stick Season,” so it’s fitting that it should provide Vermont native Noah Kahan with the inspiration for his first U.S. Top 10 hit. Kahan did need a little help, as the catalyst for its success was Olivia Rodrigo’s cover of the song for BBC Radio 1 that went viral on TikTok, but the vulnerable, folk-flecked “Stick Season” was highly accessible on its own terms. Further hits from his third album (also Stick Season) such as “Northern Attitude” and “Dial Drunk” have since revealed this talented singer-songwriter has plenty more of a similar caliber in the tank.
Neil Diamond: September Morn
Co-written with French singer/actor Gilbert Becaud, Neil Diamond’s poised, lushly-orchestrated “September Morn” is arguably less well-remembered than his preceding hit “Forever In Blues Jeans,” but it charted three places higher and remains a fan favorite. With hindsight, it’s not hard to hear why, for the singer matched the song’s swirling backdrop with a finely-wrought lyric about the elusiveness of love (“Two lovers playing scenes from some romantic play/September morning can still make me feel that way”) which is steeped in autumnal imagery, yet hits home at any time of year.
U2: October
U2’s underrated second album October captured the young, pre-fame Dublin quartet at its most earnest and idealistic. One of its many introspective highlights was its somber titular song: an especially sparse hymnal framed by The Edge’s elegiac piano figures and a suitably minimal Bono lyric, which in just a few simple lines (“The trees are stripped bare of all they wear”) perfectly encapsulates the feel of autumn at its most transitional.
Big Star: September Gurls
Alex Chilton reputedly wrote “September Gurls” (sic) because he was seeing several different girls simultaneously in the period before Big Star recorded its second album, 1974’s Radio City. As Chilton was born in December, the song’s chorus line (“December boy’s got it bad”) suggests it was at least semi-autobiographical, but what we do know for sure is that “September Gurls” was – and remains – a glorious power pop classic with more than a little autumnal melancholy running through its bones.
Nick Drake: Northern Sky
U.K. newspaper The Guardian once described Nick Drake’s “Northern Sky” as the most unabashedly joyful in his canon and the Bryter Layter highlight certainly captures the enigmatic British singer-songwriter at his most poetic, with a lyric (“I never felt magic crazy as this/ I never saw moons, knew the meaning of the sea”) steeped in romantic imagery. However, much of the song’s success is also due to John Cale’s input, with the ex-Velvet Underground man’s elegant piano figures and hymnal organ evoking the fall’s burnished beauty.
Taylor Swift: Cardigan
Several of Taylor Swift’s most emotionally fragile songs are rooted in the fall, with the season coming to the fore in no uncertain terms on “All Too Well (Sad Girl Autumn Version),” the piano-based reinvention of the 10-minute Red break-up song that topped the Billboard 200 in 2021. Intriguingly, the piano used for that track was the same one Aaron Dessner played on another of Swift’s beguiling autumnal beauties, Folklore’s trailer hit “Cardigan” which also shot straight to No. 1 on release.
Ella Fitzgerald & Louis Armstrong: Autumn In New York
Written by Vernon Duke in 1934, jazz standard “Autumn In New York” has also been recorded by legendary artists such as Frank Sinatra, Sarah Vaughan and Billie Holiday, but there’s something especially affecting about the version Ella Fitzgerald and Louis Armstrong recorded for their 1957 collaboration, Ella And Louis Again. Slow and steady, with the duo taking separate verses, their take of the song portrays both the promise and positivity (“it lifts you up when you’re run down”) and the inherent melancholy (“dreamers with empty hands/they sigh for exotic lands”) of the fall in the post-war Big Apple and it remains as enchanting as ever today.
Norah Jones: Don’t Know Why
As the first single released from her multi-platinum debut album, Come Away With Me, “Don’t Know Why” was probably the first Norah Jones song many people heard. It remains a beguiling introduction to her oeuvre, too, with Jones’ smoky vocal perfectly complementing the music’s dreamy grace and creating a mood which contains both the warmth and melancholy of the fall.
The La’s: There She Goes
In retrospect, the only surprising thing about The La’s “There She Goes” is that it was never went to No. 1. Only a minor hit on release in 1988, it did crack the U.K. Top 20 two years later, but it still only peaked at No. 13. Nonetheless, Lee Mavers’ greatest song has thrived, with its legend building through appearances in everything from Hollywood movies (So I Married An Axe Murderer) to TV shows (Gilmore Girls) before it wowed a younger generation and went viral on TikTok in 2023. As close to perfection as chiming guitar pop gets, “There She Goes” is a classic song for all seasons but one with a distinctly autumnal vibe.
