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

BIRDS OF A FEATHERBillie Eilish

Billie Eilish – BIRDS OF A FEATHER (Official Music Video)

September, when the summer bustle has faded and a hint of sentimentality sets in.

In a season like this, there’s one song by Billie Eilish that truly resonates.

It’s a track from her acclaimed 2024 album “HIT ME HARD AND SOFT,” which became a hit, reaching No.

2 on the Billboard Hot 100.

The song tells of an eternal love that endures even beyond death—a devoted, single-hearted desire to stay forever with a fated partner.

Its mellow, ’80s-tinged synth sound melds with her signature whispery vocals to create a bittersweet yet beautiful world.

It’s the perfect companion for long autumn nights when you want to feel the bond with someone special even more deeply.

Cornelia StreetTaylor Swift

Taylor Swift – Cornelia Street (Official Audio)

When it comes to the most depressing time of year, many people would say May, but a lot might picture September as the next in line.

Taylor Swift’s “Cornelia Street” is a perfect fit for the melancholic mood of September.

It portrays a woman who grows anxious at the thought of losing the person she loves.

At first glance it seems like a love song, but it’s said to actually be about Taylor Swift’s friend Karlie Kloss, with whom she reportedly fell out.

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DaylightDavid Kushner

David Kushner – Daylight (Official Music Video)

Singer-songwriter David Kushner, known for his deep baritone voice and gothic aesthetic.

Released in April 2023, this song is perfect for the slightly melancholic air of September, when the summer clamor recedes.

The lyrics depict the contradictions within the human heart—light and darkness, desire and guilt—while the weighty piano and strings dramatize that inner conflict.

It’s also known as the song used in the Giorgio Armani Acqua di Giò commercial.

Its high level of craftsmanship is evident from winning the grand prize at an international songwriting competition.

As summer draws to a close, give it a listen when you want to sink into a sentimental mood and lose yourself in thought.

Stick SeasonNoah Kahan

Noah Kahan – Stick Season

Noah Kahan is a singer-songwriter drawing global attention with a pop sound infused with folk.

His music, which honestly portrays the landscapes of his hometown and his inner conflicts, resonates with many.

The work of his I recommend for September is the title track from his album “Stick Season,” released in October 2022.

The album centers on the somber season in New England after the leaves have fallen and before the snow arrives.

Riding on a wistful folk sound, it sings of lingering feelings for a past love and complicated emotions toward his hometown, evoking a gentle melancholy.

It’s a perfect number to listen to under the slightly sentimental September sky that hints at summer’s end, as you reflect on days gone by.

I Had Some Help (feat. Morgan Wallen)Post Malone

Post Malone – I Had Some Help (feat. Morgan Wallen) (Official Video)

Post Malone, who freely traverses not only hip-hop but also rock, pop, and more, enjoys worldwide popularity.

In 2024, he teamed up with hit country singer Morgan Wallen to create the lead single from his album F-1 Trillion.

The track became a massive hit, topping Billboard’s year-end Songs of the Summer chart.

Despite its upbeat, breezy country sound, the lyrics depict a push-and-pull between a man and a woman over who’s to blame for a broken relationship, with the narrator insisting, “It’s not all my fault,” subtly shifting responsibility.

As the bustle of summer fades and September invites quiet reflection, the song’s bittersweet undercurrent—hidden beneath its cheerful melody—feels like an uncanny companion to the sentimental mood of early autumn.