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[2025 Edition] A roundup of popular and classic Western songs to listen to in September

September, when the summer heat gradually softens, heralds the start of the new school term and the beginning of autumn.

If you’re a student, fall is packed with events, yet it can also be a time that leaves you feeling a bit sentimental.

In this article, we’ve researched classic Western songs perfect for September and selected timeless tracks that many people can enjoy!

From legendary songs that quite literally take “September” as their theme to the latest mellow tunes ideal for early autumn, we’ve got you covered—making this a great read for anyone building a seasonally themed playlist.

[2025 Edition] A roundup of popular and classic Western songs to listen to in September (61–70)

Pale SeptemberFIONA APPLE

This is a song placed ninth on the debut album released in 1996 by American singer-songwriter Fiona Apple.

It was produced by Andrew Slater, owner of her label, Clean Slate.

He became interested after hearing her demo tape, later saying in an interview, “She was interested in hip-hop, while also being well-versed in classical composers.” He also said, “She loved old-school singers like Ella Fitzgerald, and I tried to fuse all those elements,” and the song reflects that eclectic mixture.

Hometown GloryAdele

Adele – Hometown Glory (Official Music Video)
Hometown GloryAdele

A track from the studio album “19.” From the very beginning, the melancholic piano tone draws you in.

In the atmosphere of lyrics that quietly illuminate the path she has walked so far and the road she should take from here, you can sense her inner strength.

It’s a song that suits the darkening autumn sky perfectly.

Please give it a listen.

Rise & Fall ft. StingCraig David

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

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.

Hold OnAlabama Shakes

Alabama Shakes – Hold On (Official Video)
Hold OnAlabama Shakes

They’re a powerhouse act who were nominated for Best New Artist at the 2013 Grammy Awards, with this track also earning a nomination for Best Rock Performance.

It’s a captivating song featuring a heavy guitar sound and the explosive vocals of frontwoman Brittany Howard.

The perfectly timed breaks hit exactly where you want them, making it incredibly satisfying!

I Built a FriendAlec Benjamin

Alec Benjamin – I Built a Friend (MUSIC VIDEO)
I Built a FriendAlec Benjamin

Singer-songwriter Alec Benjamin, who has gained popularity with a sound rooted in indie and folk-pop.

He broke out in 2018 with “Let Me Down Slowly,” and he’s continued to drop hit tunes into the 2020s.

Among his works, a song that’s especially perfect for September is “I Built a Friend.” Its acoustic, chill tone matches the wistful mood of September perfectly.

Keeps On FallinBabyface & Ella Mai

Babyface & Ella Mai – Keeps On Fallin (Official Audio)
Keeps On FallinBabyface & Ella Mai

If this song gives you a sense of nostalgia, you’re probably well-versed in early ’90s R&B or spent your youth in that era.

In June 2022, the world-renowned music producer and singer-songwriter Babyface released the track “Keeps On Fallin,” featuring Ella Mai, the hugely popular UK-born songstress in today’s R&B scene.

As mentioned at the outset, while it’s a contemporary track, it’s steeped in a nostalgic vibe that recalls classic R&B, drawing on the melody and track of Tevin Campbell’s 1993 hit “Can We Talk,” which Babyface produced and which became a massive success.

For Babyface, it can be seen as a kind of self-homage, resulting in a fresh song where nostalgia and modernity intersect.

This kind of refined R&B is sure to be a perfect fit for long autumn nights!

AutumnBelle Mariano x Ben&Ben

Belle Mariano x Ben&Ben – Autumn (Music Video)
AutumnBelle Mariano x Ben&Ben

This work is characterized by its translucent vocals and melodies that seep into the heart.

It’s a collaboration between Belle Mariano and the Filipino folk-pop band Ben&Ben, released in December 2023.

The song is also featured on the soundtrack of the ABS-CBN drama “Can’t Buy Me Love,” with lyrics that poignantly overlay the sorrow of long-distance love and the pain of parting with autumnal imagery.

Ben&Ben’s delicate acoustic arrangement and Belle Mariano’s gentle vocals blend beautifully, making it a track you’ll want to savor on long autumn nights.

It’s a moving song that resonates with those who have experienced a breakup or are in a long-distance relationship.