[2026] Classics and Recommended Popular Western Songs to Listen to in October

Dear OctoberPhantom Youth

Phantom Youth – Dear October

Phantom Youth is a music project based in Munich, Germany.

Blending dream pop and lo-fi into an alternative sound, the project has been drawing attention in the indie scene.

Here’s one track from their catalog that’s perfect for October.

The song feels like a personal, introspective message addressed to “Dear October,” leaving a strong impression.

Airy guitars and a nostalgic melody evoke a sentimental longing for seasons gone by.

Released as a single in February 2023, the track is also included on the mini-album Promises.

If you’re looking to get lost in music alone on an autumn night, deep in thought, this one will be right in your strike zone.

Last LetterWitt Lowry

Witt Lowry – Last Letter (Official Music Video)

Witt Lowry is a rapper who’s gained popularity for his raw, emotionally honest style.

He originally studied graphic design before switching paths to music, giving him a unique background.

Among his works, this is the song I recommend when you want to sink into October’s melancholic mood.

Over a poignant piano melody, he delivers powerful verses about his father—who died of cancer in October 2015—and his parents’ divorce.

That unvarnished emotional expression resonates deeply with listeners.

Released in August 2017, the track is also included on the acclaimed album “I Could Not Plan This.” It’s perfect for a quiet night alone—be sure to give it a listen.

OctoberToosii

Toosii – October (Official Video)

Toosii, a next-generation rapper gaining attention for his philosophical lyrics, has crafted a track titled “October” that, as the name suggests, centers on the month of October.

The key point of the lyrics is how he frames autumn as “the season between summer and winter.” Summer evokes a fun, bright image, while winter feels harsh and cold.

In other words, autumn marks the passage from a joyful season toward a tougher one.

Keep that in mind as you listen.

Also pay attention to the rhythmic flow and the cool production.

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emails i can’t sendSabrina Carpenter

Sabrina Carpenter – emails i can’t send (Official Audio)

A soulful track by Sabrina Carpenter that expresses the deepest emotions of the heart through music.

The self-titled song from her album “emails i can’t send,” released in July 2022, is a piece that reflects her complicated feelings toward her father.

Having experienced the family pain of infidelity, she candidly sings about inner conflict, loss of trust, and the hope for reconciliation.

It must have taken courage to lay bare such personal experiences.

Yet it’s precisely that sincerity that resonates with listeners.

Including lyrics in which the date October 13 holds special meaning, be sure to check out the lyrics while listening this October.

One October SongNico Stai

Nico Stai – One October Song

Nico Stai is a singer-songwriter born in Spain and based in Los Angeles.

His music is captivating for its lyricism and melancholic atmosphere, reminiscent of Elliott Smith.

One of his songs themed around October is included on the album “PARK LOS ANGELES.” The track beautifully captures the bittersweet feeling of faded memories resurfacing as autumn deepens.

Released on the 2006 album, it was featured in an emotional scene in the TV drama “Chuck,” earning high praise from fans.

It’s a moving piece, perfect for a quiet autumn night of solitary reflection.

October SkyYebba

Yebba – October Sky (Live)

Singer-songwriter Yebba is known for crafting many heart-wrenching songs.

One such track included on her album Dawn is October Sky.

It’s a song themed around the October sky, depicting children watching rockets launched into the beautiful heavens, contrasted with adults being swept along by the crowd.

If you interpret the rockets as a metaphor for farewell and the adults as the children grown up, it all seems to fall into place.

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Shoot the MoonNorah Jones

Shoot The Moon

Norah Jones is a singer-songwriter whose father is a world-renowned sitar player.

She’s known for her languid, jazz-tinged songs.

Shoot the Moon is her debut track, and even at that time her current style was already taking shape.

The lyrics depict parting from a lover or someone dear, layered with the imagery of summer fading away.

It’s the perfect song for October, when the traces of summer vanish.

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