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.

We Could Go Back ft. MoelogoJonas Blue

Jonas Blue – We Could Go Back ft. Moelogo (Official Video)

Here’s a poignant song about continuing to think of a precious person even after heartbreak.

The story-driven music video set in a big city adds an extra layer of sentimentality.

The lyrics—enduring loneliness and the absence of someone dear while standing alone in the heart of a metropolis—fit perfectly with the autumn breeze.

In contrast to the melancholic words, the relatively upbeat, pop-leaning sound makes it very easy to listen to.

It’s a track you’ll want to watch the MV for while reflecting on the meaning of the lyrics.

Harvest MoonNeil Young

Neil Young – Harvest Moon [Official Music Video]

Singer-songwriter Neil Young has worked across a wide range of genres, from hard rock to country rock, and is famous as a legendary rock artist.

His “Harvest Moon” is one of his signature songs.

While it didn’t become a massive hit, it remains a beloved piece.

The lyrics carry strong religious overtones, and the melody is crafted to match that atmosphere with a romantic touch.

I think you’ll enjoy it even more listening under the chilly October sky.

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.

OctoberGeorge Ogilvie

October

Singer-songwriter George Ogilvie is known for music that is rich in emotion and deeply introspective.

His track released in November 2016 resonates as a song that symbolizes the loneliness of autumn and the season of change, leaving a profound impression on listeners.

Characterized by soulful, emotive vocals and a simple yet beautiful acoustic sound, it encapsulates his musical style well.

Centered on themes of personal experience and the complexities of friendship, it strikingly evokes nostalgia for a simpler time in the past.

It’s a perfect song for long autumn nights of reflection—and it also makes a great soundtrack for a drive.

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.

NikesFrank Ocean

Frank Ocean – Nikes (Music Video)

A song that critiques materialistic modern life in pursuit of the latest trends.

It was released in 2016.

It samples The Mohawks’ 1968 track “The Champ.” The music video, filmed in London, was directed by Tyrone Lebon.