RAG MusicAutumn song
Lovely autumn song

[2026] A roundup of classic Western songs perfect for cloudy days

Suddenly, but on those overcast days when you can’t even catch a glimpse of blue sky, what kind of music do you listen to? Staring at a dull sky can make it hard to get in the mood, but plenty of people probably go for upbeat tracks that blow those feelings away.

In this article, we’ve gathered the latest numbers—especially in the first half—featuring bright, refreshing tunes and chill tracks that help soothe the mind.

The latter half introduces many timeless classics, so be sure to add them to your cloudy-day playlist!

[2026] A roundup of classic Western songs to listen to on cloudy days (41–50)

It’s RainingDarts

It’s a song with strikingly sentimental, self-deprecating lyrics.

Musically it’s in a major key, but what it sings about is things like “I’m drowning in misfortune,” “It’s raining, and I’m sinking, I’m dying, I’m crying.” It must be that sadness keeps raining down in the heart.

True to the title “It’s raining,” I feel the song depicts the very moment when one is in a painful, heartrending situation, with tears falling like rain.

Listening again while savoring the lyrics, I realized that although the tune is in a major key, it still carries a sense of emptiness.

One More Rainy DayDeep Purple

With its rare sound and vocals for Deep Purple, it gives the impression that fans who only know their peak era might be surprised, even taken aback.

What is this freshness? It’s a song that made me rediscover, in a sense, another appeal of Deep Purple—realizing they also sang such a refreshing tune.

SeptemberEarth, Wind & Fire

Earth, Wind & Fire – September (Official HD Video)
SeptemberEarth, Wind & Fire

A timeless classic you can’t leave out when talking about disco music: “September.” It’s one of the signature songs by the funk band Earth, Wind & Fire.

The sparkling brass section and soaring vocals evoke a clear, refreshing autumn sky.

Although the title “September” refers to the ninth month, the song is actually about someone in December who can’t forget the person they met in September.

You’d naturally assume it’s a song about September, right? Either way, it’s a light, irresistible track that makes you want to start dancing!

DreamsFleetwood Mac

Fleetwood Mac – Dreams (Official Music Video) [4K]
DreamsFleetwood Mac

Fleetwood Mac is an indispensable rock band when discussing the UK soft rock scene, drawing attention with their gentle, uniquely crafted band sound.

Dreams, included on their 1977 album Rumours, is a medium-tempo track perfect for a mellow listen on a rainy day.

Stevie Nicks’s clear, translucent vocals ring out alongside the band’s tender performance, leaving a strong impression.

The song portrays feelings toward a struggling lover, with poetic lyrics that liken the band’s relationships to “rain” and “thunder.” Even if the eye wanders to someone else, the sentiment that “in the end, you’ll understand” resonates throughout.

It’s a song that pairs beautifully with a blue, rainy-day mood—give it a listen.

You Can Do MagicAmerica

This is a famous Western song from the United States by an artist known for a bright, smooth style centered on richly textured country sounds.

Its memorable melodic sense is outstanding, making it a track you’ll want to listen to on cloudy days.