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Classic Western songs perfect for a cloudy day

You know those dull, overcast days when the sun never peeks through? This time, I’m putting together a selection of classic Western songs perfect for those cloudy days.

From tracks that suit the gray weather to refreshing tunes that lift your spirits, I’ll introduce a variety of songs.

Top 10 classic Western songs to listen to on a cloudy day

How Will I KnowWhitney Houston

Whitney Houston – How Will I Know (Live from Welcome Home Heroes with Whitney Houston)
How Will I KnowWhitney Houston

This is a classic Western pop song by Whitney Houston, whose overwhelming vocal sensibility and smooth singing voice create an exceptionally pleasant listening experience and have earned her immense trust.

With a refreshing, deeply flavorful mood, it’s a piece you’ll want to listen to on a cloudy day.

Sweet LoveAnita Baker

Anita Baker – Sweet Love {Actual Video}
Sweet LoveAnita Baker

This is a classic Western song by Anita Baker, a vocalist with deep, soulful music whose artistry has made her immensely popular—especially on vinyl.

With sophisticated wordplay that heightens the sense of exhilaration, it’s a work you’ll want to listen to on a cloudy day.

A Thousand MilesVanessa Carlton

A beautifully clear piano intro.

So striking that it sticks in your ears after just one listen, this is A Thousand Miles, released in 2001.

It’s known as the signature song of American singer-songwriter Vanessa Carlton and became a worldwide hit.

It’s also extremely popular in Japan, with many renowned musicians openly calling themselves fans of the track.

Adding fuel to its popularity was Taka from the hugely popular rock band ONE OK ROCK.

He covered A Thousand Miles in an acoustic version at his own live shows, which brought renewed attention to the song.

Truly great songs never fade with time.

Great Western songs to listen to on a cloudy day (11–20)

Sunny InsideNeil Young

Included on the 1988 album “This Note’s for You.” A Canadian singer-songwriter born in 1945.

It’s a track from the album released under the name Neil Young & The Bluenotes.

The melodic progression, which somehow evokes Japanese kayōkyoku, gives a nostalgic feel when you listen to it.

Big FunInner City

Inner City – Big Fun (1988)
Big FunInner City

This is a renowned classic by Inner City, celebrated for its refreshing vocals and big-room sound that perfectly matches its commanding melody line.

It’s a superb mood-setter you’ll want to play on cloudy days, letting you savor its invigorating, uplifting atmosphere.

JoannaKool and The Gang

It’s a classic Western pop song by Kool & the Gang, renowned as artists who showcase an overwhelming sense of style with a focus on funky grooves.

Its outstandingly refreshing mood is the hallmark, resulting in a refined, slightly gritty finish that makes you want to listen on a cloudy day.

Into The GrooveMadonna

Madonna – Into The Groove (Official Video)
Into The GrooveMadonna

It’s a classic Western pop song by Madonna that builds a danceable track, unleashing a catchy digital pop sound with exceptional taste.

The refined composition stands out with a refreshing feel, making it something you’ll want to listen to on a cloudy day.