10. Bridget St. John – Ask Me No Questions (1969, Dandelion)

Singer-songwriter Bridget St. John became a British cult figure in the wake of her critically-lauded sophomore LP Songs for the Gentle Man (1971), though it’s in her debut album Ask Me No Questions (1969) that the artist taps into her signature sound in ways no-holds-barred and divinely autumnal. She sings like Nico and plays like Nick Drake, particularly during the former’s Chelsea Girl period and the latter’s Pink Moon days; an intoxicating mix that’s garnered, inexplicably, less critical adoration than the work of those two giants.

The titles alone of tracks like “Autumn Lullaby” and “The Road Was Lonely” conjure images of pastoral melancholy and chlorophyll-drained woodland, but it’s in songs like “Curl Your Toes” and “The Curious Crystals of Unusual Purity” that St. John best captures the duplicitous essence of the season. There are tinges of comfort, but mostly of longing; a sedentary warmth roused by the impetus of plunging temperatures, birds migrating, leaves changing color. St. John’s right. There are no questions to be asked; the music speaks for itself. One only wonders why radio jockeys failed to play her work in its time.

Listen for: “Curl Your Toes”

9. Connie Converse – How Sad, How Lovely (2009, Squirrel Thing Recordings)

Few singer-songwriters point to Connie Converse as a key progenitor of their work, but they should. The New Hampshire-born Manhattanite is often regarded as the “inventor” of the singer-songwriter genre, though her music remained obsolete until little over a decade ago, when a collection of never-before-heard, lo-fi demos were released in the form of a compilation album,
How Sad, How Lovely, courtesy Squirrel Thing Recordings. Converse never explicitly sings of autumn, though her songs possess a haunting, lovelorn quality congruent with the saudade of the season.

“Roving Woman”, a brilliant feminist ditty and one of the album’s highlights, charts Converse’s inner conflict with staying or leaving — the tensions of transformation as one, at a certain age, deliberates between settling down or living nomadically: “People say a roving woman / Is likely not to be, better than she ought to be / So when I stray away from where I’ve got to be / Someone always takes me home.” It, too, prophesies Converse’s own trajectory: disillusioned with her lack of success (save for one live performance on The Morning Show with Walter Cronkite in 1954), and feeling alienated from modern American life, Converse disappeared in her Volkswagen Beetle in 1974 and was never heard from again.

That confounding reality often renders
How Sad, How Lovely a ghostly endeavor; it’s also what makes it brilliant. The compilation is ephemera embalmed, the eternal document of an artist defined by inner restlessness and ultimate transience… perfect listening, then, for the most transient and restless of seasons.

Listen for: “Talkin’ Like You (Two Tall Mountains)”

8. Bob Dylan – Nashville Skyline (1969, Columbia)

Even Bob Dylan detractors will find something to love about this album. The songwriting behemoth eschews the image he built fastidiously (albeit behind his “coolly disaffected” facade) in the early ’60s, even temporarily quitting smoking to smooth over a characteristically-gritty voice in favor of a honey-smooth country croon. Nashville Skyline finds Dylan longing for where “the snowflakes storm… [where] the rivers freeze, and summer ends”, for the days when he “held mountains in the palm of [his] hand”. It also finds him in the nighttime, when it’s “the right time to be with the one you love”, and discovering that “you can have your cake and eat it, too”.

Treading those fine lines between hope and regret, love and longing, reckoning and redemption, Nashville Skyline simultaneously looks back on a decade and forward to the next one. Critics and fans would eventually label Blood on the Tracks (1975) his magnum opus, but the rural-tinged LP he’d release onto an unsuspecting public in the year of Woodstock, Manson, Altamont, and Nixon, retains an autumnal magic unmatched. It’s a work of jubilation but also one of taking stock — undulating through banjo strings beneath the naked limbs of an oak tree in a blue sky.

Listen for: “Girl from North Country”

7. Vince Guaraldi – It’s the Great Pumpkin, Charlie Brown: Music from the Soundtrack (2018, Concord)

This one feels especially important in 2020, considering Apple TV’s recent acquisition of all Peanuts content — beginning with Great Pumpkin‘s removal from the ABC line-up for the first time in 54 years. Fans have taken to social media with their outrage, and understandably so. It’s the Great Pumpkin, Charlie Brown is essential October viewing and remains one of the best-loved and ubiquitous of all holiday cartoon specials (along with its yuletide counterpart, A Charlie Brown Christmas), in large part due to Vince Guaraldi’s distinguished score.

Throughout, Guaraldi weaves the cozy urbanity of his jazz roots with “back to the land”-inflected woodwinds emblematic of the burgeoning counterculture. It’s a simpatico union, synthesized to greatest effect in “Fanfare/Breathless/Trick or Treat (Reprise)”, the underscore to Snoopy’s Red Baron dreamscape, rife with anti-war subtext. But listeners may ultimately find the most comfort in Guaraldi’s lighter fare, particularly the gorgeous “Great Pumpkin Waltz” and “Happy Linus” or, in other words, the sounds of childhood.

Listen for: “Great Pumpkin Waltz”

6. Joni Mitchell – Clouds (1969, Reprise)

Joni Mitchell’s sophomore LP may be best known for winning the artist her first Grammy Award and finally bringing fans her own recording of “Both Sides, Now” (she’d written it years before, and the pop cover by Judy Collins had already hit the Billboard Top 10 in ’68) — but there’s much to offer here. For example, “Songs to Aging Children Come”, a deep cut rich in chromatic harmonies so potent they sound a capella, echoed with an autumnal witchery plaintive enough for Arthur Penn’s Thanksgiving-set hippie classic Alice’s Restaurant (1969), which features (an inferior, though still haunting) cover of the song during the funeral scene.

Throughout, there’s a rawness (naïveté, even) that feels very pre-Blue, though that’s far from a critique. To this day, Clouds remains an incandescent mosaic of lyric and sound, resplendent with offbeat tunings symptomatic of the season’s emotional and atmospheric gallimaufry, whose medley of classics (“Chelsea Morning”, “The Fiddle and the Drum”) and lesser-known gems (“The Gallery” and “That Song About the Midway”) make for perfect cool weather listening.

Listen for: “Songs to Aging Children Come”

5. Laura Nyro – More Than a New Discovery (1967, Verve Folkways)

Of the myriad singer-songwriters that emerged from the Woodstock generation, Laura Nyro is often held in high critical esteem while staying slim on record sales compared to such luminaries as Carole King, James Taylor, and Carly Simon. Perhaps it’s because her approach to music is anything but categorical — marrying the folksier, confessional sensibilities of her late ’60s contemporaries with a bombastic Brill Building-meets-Big Band-meets-Broadway sound. The apotheosis of her own personal “genre” came at the tail-end of the decade, with the release of a career high-water mark, Eli and the Thirteenth Confession (1968), and its experimental follow-up New York Tendaberry (1969).

Overlooked remains her debut LP, the consistently extraordinary More Than a New Discovery — odd, considering the number of hits it yielded for other artists (with the 5th Dimension taking “Wedding Bell Blues” to No. 1 on Billboard two years later). Perhaps the most “accessible” release in her catalogue, Nyro’s inaugural effort careens from the joyous to the somber to the surreal, crystallizing dichotomies left and right in ways that make some of its darkest tunes also its most comforting. “Billy’s Blues”, a meditation on depression, sounds like dinner music, while “He’s a Runner” and “Buy and Sell”, exploring abandonment and addiction, respectively, are rendered with the soulful quiet of a church hymn. From start to finish, it’s an ideal soundtrack for strolling through the park on a cool September morning or donning a scarf and peacoat while sipping an Old-fashioned.

Listen for: “Blowing Away”

4. Jackson C. Frank – Jackson C. Frank (1965, Columbia/EMI)

Jackson C. Frank’s sole studio effort remains lost on most “greatest albums” compendiums, and it’s a mystery considering the number of artists — and albums — that sole venture inspired. An eventual landmark of the American folk revival and an early blueprint of the singer-songwriter “mold,” Frank’s self-titled LP, produced by Paul Simon at CBS Studios in London, is a bleak, often terrifying set characterized by longing and broken hearts.

Its best tracks would be covered, later, to equally-haunting effect by a young Nick Drake (namely “Blues Run the Game”, “Here Come the Blues”, and “Milk and Honey”, a similarly little-known folk luminary who died young and found fame posthumously. Frank’s acoustic guitar matches his doleful cries on fatalistic meditations about locks “that can’t be broken, and there isn’t any key.” Why listen to such murkiness? Frank’s music is not created in vain — it’s about finding light leaks in the darkness. Harvest moons sometimes shine in the blackest of skies.

Listen for: “Blues Run the Game”

3. She & Him – Classics (2014, Columbia)

Cover albums rarely do their original material justice. So often, contemporary artists interpreting old standards turn in loose facsimiles, rarely fitting tributes. Modern-day folk-pop duo Zooey Deschanel and M. Ward, operating under the moniker “She & Him”, defy expectations on their fifth studio album Classics, which evokes a “sit by the fire and spin some vinyl” timbre different from their earlier recordings — in particular, their stellar debut and sophomore efforts, which engender a sprightly spring flavor without ever being cloying.

The duo electrifies pop hits that could use a little dusting, like Dusty Springfield’s saccharine 1964 classic “Stay Awhile”, while opting to go subtle on some of the “bigger” numbers, like the Righteous Brothers’ “Unchained Melody”, which benefits greatly from Deschanel’s diaphanous lilt and the Chapin Sisters delivering spectral murmurs on backup. Critics were quick to characterize Classics as “grandma music” when it came out in time for Christmas, 2014. Such a label intimates that Classics is geared towards one demographic, or that by being made with a certain audience in mind (here, according to one critic, older women), it’s ultimately of little value. Both assessments prove blinkered as soon as the needle drops — optimally, on a rainy November afternoon, curled up in the arms of a lover.

Listen for: “Would You Like to Take a Walk?”

2. Vashti Bunyan – Some Things Just Stick in Your Mind: Singles and Demos, 1964 to 1967 (2007, FatCat)

Better save this one for the end of November. Vashti Bunyan’s 2007 compilation retains a wintry bite and a makeshift, mid ’60s zeitgeist perfect for a pre-Christmas warm-up. Some tracks could themselves be Christmas songs, like Bunyan’s alchemical duet with Twice As Much on “Coldest Night of the Year”, a genuinely charming alternative to “Baby, It’s Cold Outside” that seems tailor made for a Rankin/Bass cartoon. Replete with horns, woodwinds, clapping, and bells on the lavishly-produced studio fare, mixed with a stripped-down sound on the artist’s homemade demos (featuring only her voice and guitar), it’s bewildering knowing Bunyan never found chart success in her day, and that it would take 30 years for her debut (and for a while, sole) studio album, 1970’s Just Another Diamond Day, to gain a cult following.

Fortunately, Some Things Just Stick In Your Mind proves a redemptive release, fitting for the post-summer months, particularly with tracks like “I Want to Be Alone”, “Train Song”, “Love Song”, and the LP’s jubilant namesake penned by Mick Jagger and Keith Richards.

Listen for: “I’d Like to Walk Around in Your Mind”

1. Nick Drake – Bryter Layter (1971, Island)

Declared one of the greatest albums of the 1970s by NME and ranked 23rd in Q’s compendium of the 100 Greatest British Albums Ever, Nick Drake’s Bryter Layter is a triumph of folk-jazz, capturing the halcyon bliss of sun-kissed September afternoons and the heartsick magic of frigid December nights. It comes as no surprise that Wes Anderson would sample one of the album’s most glittering tracks, “Fly”, for his 2001 classic The Royal Tenenbaums. Like Anderson’s film, Drake’s album is a tone poem of intemperance and reconciliation, retrospection and reinvention, tied up in a svelte bow that oozes style without trying too hard.

Detractors of Bryter Layter comment on the album’s polished production, owed to the contributions of session musician and Velvet Underground alum John Cale. Similarly, Drake’s intent of hitting it big on the pop charts with Bryter Layter is viewed by dissenters as a superficial aim, one that renders the album “inferior” to his subsequent work, Pink Moon (1972). But comparing the two is folly. Their contexts are completely disparate — Pink Moon, Drake’s sparsest outing, is best left for seasonal extremes (the dead of winter or summer’s humid mire) — while Bryter Layter remains both a transitional work and a masterpiece of stylistic synergism.

Pastoral and urbane all at once, it combines genres while keeping a through-line of lyrical introspection (as in all of Drake’s work). But looking inward, here, is not a masochistic exercise, nor one that demands an epiphany. Bryter Layter asks you to stay where you are. To simply be. Let Drake’s voice wash over you. I can promise — you’ve never felt magic crazy as this.

Listen for: “Northern Sky”