Classic and popular Western songs to listen to in October 2025

Visions of JohannaBob Dylan

Bob Dylan – Visions of Johanna

How about taking your time on a long autumn night to carefully unravel some English song lyrics? Bob Dylan is a world-renowned artist who has even won the Nobel Prize in Literature.

It’s no exaggeration to say that his arrival changed the world.

His song “Visions of Johanna,” with its story-like structure, leaves you with the lingering afterglow of having read a short novel once you finish the lyrics.

Grey OctoberBoldy James (feat. Evidence)

Boldy James feat. Evidence “Grey October” Official video

A rap song that evokes a gray October sky, steeped in a melancholic mood.

Featuring Boldy James’s cool, razor-sharp flow intertwined with Evidence’s philosophical lyrics, this track appears on the album “The Price of Tea in China,” released in March 2020.

The Alchemist’s jazzy, weighty beat brings out the best of boom-bap style hip-hop.

The lyrics, depicting the realities of street life and inner conflict, are perfect for autumn introspection—an ideal pick for a dusk drive or a quiet night by the window.

Autumn LeavesChris Brown ft. Kendrick Lamar

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

The masterpiece “Autumn Leaves,” a collaboration between Chris Brown and Kendrick Lamar, is, as the title suggests, a perfect October track themed around autumn.

When we think of autumn songs, we usually imagine somber melodies or relaxed tempos.

This song, however—sung by Chris Brown—has a very stylish track with strong R&B elements.

By the way, despite being themed around autumn, the music video frequently features cherry blossoms (lol).

Summer SkinDeath Cab for Cutie

Death Cab for Cutie – Summer Skin (‘Directions’ Music Video)

A love song included on Plans, the fifth album by the indie rock band Death Cab for Cutie, released in 2005.

The album reached No.

4 on the Billboard album chart and was nominated for a Grammy Award.

Tiimmy TurnerDesiigner

Desiigner – Tiimmy Turner (Official Audio)

A song by American hip-hop artist Desiigner, released as a digital download in 2016.

It was produced by Mike Dean, a longtime collaborator of Kanye West.

The track was selected for Rolling Stone’s “50 Best Songs of 2016.”

Secret OktoberDuran Duran

Secret Oktober (2010 Remaster)

“Secret Oktober” is a song by the British rock band Duran Duran, included as the B-side to the 1983 single “Union of the Snake.” It was later featured on the 2010 remastered edition of the album “Seven and the Ragged Tiger.” The single reached the top 10 in various countries and peaked at No.

3 on both the UK and US charts.

“Secret Oktober” was also chosen by many fans as the “most enigmatic Duran Duran lyric” in a question posed on the band’s official Twitter.

Don’t you think “Secret Oktober” is the perfect track for the wistful mood of October?

Sun It RisesFleet Foxes

Fleet Foxes – Sun Giant/Sun It Rises live In The Basement

A song included on the self-titled debut album released in 2008 by Fleet Foxes, a band from Seattle.

The album received high praise from many music critics and was certified Platinum in the UK and Gold in the US.