[2026 Edition] A Roundup of Popular and Classic Western Songs to Listen to in September

All Too Well (Sad Girl Autumn Version)Taylor Swift

Taylor Swift – All Too Well (Sad Girl Autumn Version) – Recorded at Long Pond Studios

Taylor Swift is a singer-songwriter who enjoys wide popularity for her broad musical range—from poppy tracks to nostalgic works rooted in country music, which is also her backbone.

She’s continued to drop numerous hit tunes, but among them, “All Too Well (Sad Girl Autumn Version)” is an especially perfect number for September.

Its cool, detached lyrics depicting the end of a romance feel just right for September, a month that evokes the close of summer.

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Ryo

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SeptemberDaughtry

Daughtry – September

Daughtry is a rock band fronted by Chris Daughtry, who made his mark on Season 5 of the popular audition show American Idol.

With a sound rooted in alternative rock and post-grunge, the band has gained popularity primarily in the United States.

As the title suggests, their song “September” is a track themed around the month of September.

While many autumn-themed songs tend to be about heartbreak, this one stands out for its positive message about making a firm decision and setting out on a journey within a limited time.

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Too Good At GoodbyesSam Smith

Sam Smith – Too Good At Goodbyes

It’s his bittersweet breakup song released in 2017.

His voice, now that he’s gotten so slim, is still as sweet as ever, and it’s definitely a recommendation for this season.

The gospel-style chorus is particularly appealing.

Give it a listen on a long autumn night.

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Yoshizaki Keiko

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Autumn LeavesEd Sheeran

Autumn Leaves (Deluxe Edition)

Ed Sheeran’s classic, “Autumn Leaves.” There’s a jazz standard with the same title, but this is a completely different song—a pop track released in 2011.

As the title suggests, it’s themed around autumn, and the lyrics liken heartbreak to leaves falling in the fall.

It’s pop, so it’s extremely easy to listen to, yet it still carries a strong sense of melancholy.

It’s a gem—be sure to check it out.

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September GrassJames Taylor

James Taylor – September Grass

James Taylor, a quintessential American singer-songwriter, has left behind a wealth of beloved classics and hit songs that continue to be cherished by many.

While he helped lead the singer-songwriter boom of the 1970s, he’s also known as a master of the acoustic guitar.

Here in Japan, too, countless listeners have admired his warm vocals and the expressive tones of his acoustic playing.

In that spirit, I’d like to introduce “September Grass,” a perfect song to savor in September that beautifully showcases Taylor’s voice and acoustic guitar.

The track opens his 15th album, October Road, released in 2002, and carries a nostalgic, bittersweet feel—evoking the sense of lying in a grassy field in September, after summer has ended, recalling the faint memories of a distant romance.

It feels like more than just a seasonal transition; it suggests a metaphor for life, moving from summer to autumn, and then sensing the approach of winter.

As the lyrics suggest, if you enjoy a drink, try listening to this song with a glass of apple wine in hand!

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KOH-1

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Rise & Fall ft. StingCraig David

Craig David – Rise & Fall (Official Video) ft. Sting

Craig David is one of the UK’s leading R&B singers.

He’s been active since the 2000s and still pops up in the mainstream from time to time.

Among his catalog, a track that’s especially perfect for autumn is Rise & Fall ft.

Sting.

It’s a collaboration with Sting and samples his classic Shape of My Heart.

It’s a sexy, mature R&B tune—definitely give it a listen.

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Late September DogsMelissa Etheridge

The Late September Dogs (Live At The Roxy)

Melissa Etheridge, who has won numerous music awards.

When it comes to songs you want to hear in the fall, isn’t “The Late September Dogs” the one? The title literally means something like “the dogs of late September.” The song is set in September and portrays the feelings of someone enduring sorrow.

Dogs appear in the lyrics, and they can be interpreted as a metaphor for the protagonist.

Why not give it a listen while letting your imagination roam?

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yamamoto

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