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

It Might As Well Rain Until SeptemberCarole King

It Might as Well Rain Until September

A single released by Carole King in 1962.

After “Take Good Care of My Baby” brought Bobby Vee a No.

1 hit in the U.

S.

, Carole King and Gerry Goffin wrote this song for Vee in 1962.

However, Vee’s management refused to release it as a single.

Don Kirshner of Aldon Music, who compared Vee’s recorded version with King’s demo, fell in love with King’s demo and decided to release her version as the single as-is—making this a song that came with some complications.

Autumn Leaves (ft. Kendrick Lamar)Chris Brown

Chris Brown – Autumn Leaves (Explicit) ft. Kendrick Lamar

R&B singer-songwriter Chris Brown, who keeps dropping big tunes and growing in popularity every time.

He’s created many classics, but the one I especially recommend for September is Autumn Leaves (ft.

Kendrick Lamar).

It’s a collaboration with Kendrick Lamar, one of the world’s top-tier rappers, and the lyrics revolve around the premonition of a breakup.

Fall in PhiladelphiaDaryl Hall & John Oates

Fall in Philadelphia

Exuding a rich AOR mood with a cool, urban vibe, Daryl Hall & John Oates are one of the quintessential blue-eyed soul artists, especially prominent from the late 1970s through the 1980s.

Though a band of both white and Black members, their sound often leans heavily into soul and funk.

Their melodies are exceptionally strong, which explains their frequent appearances on the pop charts.

On top of that, their grounding in Black music rhythms is solid enough that they could easily be categorized under the 1980s so-called “Black Contemporary.”

SeptemberDavid Sylvian

September

David Sylvian, the vocalist of the band Japan—who were hugely active from the 1970s through the 1980s—and a singer-songwriter in his own right, is one of the artists who helped energize the eccentric New Wave genre.

Among his works, the track I especially recommend is September.

Centered around the piano, it’s closer to an instrumental than a vocal piece, and throughout it presents a stylish melody that evokes the arrival of autumn.

Autumn LoveDeath Cab for Cutie

Death Cab for Cutie – “Autumn Love” (Lyric Video)

Death Cab for Cutie is a rock band that has gained popularity for its lyrical musicality.

The band is renowned for its guitar work, and their distinctive guitar sound—imbued with a sense of wistfulness and fragility—is especially captivating.

A track of theirs we recommend for September is Autumn Love.

Featured on their 2018 album Thank You For Today, the song is relatively minor within their catalog but remains a fan favorite.

Be sure to check it out.

Early AutumnElla Fitzgerald

Early Autumn

Ella Fitzgerald stands alongside Billie Holiday and Sarah Vaughan as one of the defining female jazz singers of the 20th century.

If you’ve dabbled in jazz even a little, you’ve probably heard her voice at least once.

Among her works, the one I especially recommend for September is Early Autumn.

As it’s a piece that depicts autumn, it pairs perfectly with September.

It’s also a standard, so there are many covers out there.

Be sure to compare her version with those by other singers.

The First of AutumnEnya

The First of Autumn

Enya, a quintessential artist in the New Age genre known for its soothing qualities, is also famous in Japan for her calming voice.

Among her songs, the one I recommend for September is The First of Autumn.

Released in 2000, this piece is relatively minor within her catalog, but it enjoys enduring popularity among fans for its gentle, autumn-themed melody.

If you want to spend the season with relaxing music, be sure to check it out.