Rainy Day Blues: 15 Melancholic Masterpieces for Your Rainy Day Playlist

Embrace the melancholy with 15 soul-stirring sad songs for your rainy day playlist. From Adele's haunting melodies to Leonard Cohen's introspective ballads, let the music soothe your soul as you weather the storm.

This post has been in a draft form since September 2012 and I’ve finally finished it. With the sudden passing of Prince and the tandem quintessential rainy long weekend in Sydney, here are 15 sad songs for your next rainy day playlist.

Listen to the 15 Sad Songs for your Rainy Day Playlist on Spotify

Angel – Sarah McLachlan (1998)

Oh this glorious sadness, That brings me to my knees

This song is the go to song for TV shows, movies. There is something haunting about McLachlan’s quivering voice in this song. Its such a beautiful song but listening to it will seriously wreck your day. I love this duet version with the powerhouse Pink.

Tears in Heaven – Eric Clapton (1992)

Would you know my name, if I saw you in heaven?

Written about the pain Clapton suffered after losing his 4 year old son in a freak accident in 1991.

Something – The Beatles (1969)

Don’t want to leave her now, you know I believe her now

I love this cover of Something by Jeff Lynne, Joe Walsh and Dhani Harrison (George Harrison’s son). That falsetto by Jeff Lynne, what made ELO so good. He still has the best beard and hair combo in music. Joe Walsh is a guitar legend, seeing him doing his own set of solo artist work at an Eagles concert was a highlight of the night to the same level as the solo from Hotel California.

This is probably my favourite Beatles song. That unmistakable wailing of bending guitar strings.. wow. It was written by George Harrison and released on the acclaimed ‘Abbey Road’ album. It was long rumoured that the song was written about Harrison’s wife Pattie Boyd, suspected of having an affair at the time with Eric Clapton (who she later went on to marry) but this has long been nixxed. The song has been covered over 150 times already, including by Eric Clapton himself. Harrison’s personal favourite of the cover was by James Brown. If you can handle the funk, click here to listen to it.

Behind Blue Eyes – The Who (1971)

No one knows what its like to be hated

I’ve heard this one live and my ears are still ringing from loudness of The Who concert and that was over 7 years ago! A few tie-ins to other songs in this list… Roger Daltrey has a legendary rock falsetto much like Jeff Lynne and The Who’s drummer is Zak Starkey – (Ringo Starr’s son), who is now 50 years old – hard to believe.

Nothing Compares to You – Sinead O’Connor (1990)

Its been 7 hours and 15 days, since you took your love away

This is a song written by Prince that he would never be able to reclaim after Sinead O’Connor made it her own. The film clip, a tight framed shot of her bald head, that single tear, captures it all.

Everybody Hurts – REM (1992)

When your day is night alone (Hold on, hold on)

Still holding out for an REM reunion tour…

Prince – Purple Rain (1984)

I never meant to cause you any sorrow, I never meant to cause you any pain

A musical masterpiece to accompany the movie of the same name. A Grammy award winner. This Superbowl Halftime show is one of the best you’ll see. Singing and playing live – which nobody takes the risk to do, in the bucketing rain, a slippery stage and with all that electrical equipment no less.

The memory of witnessing a 22 minute version of this song live, with a guitar solo of unknown length – will stay with me for a long time, even more so now.

Hallelujah – Jeff Buckley (1994)

It’s not somebody who’s seen the light, It’s a cold and it’s a broken Hallelujah

This song has been covered by over 300 artists over the years including KD Lang but was originally a Leonard Cohen hit.

The Day You Went Away – Wendy Matthews (1992)

And I thought that it would rain, the day you went away

They played this song during a video montage when Lizzie the dog off Backyard Blitz died and it seriously wrecked me. I’ve heard this one live too, at a local Australia Day concert. Hard.

Another Day in Paradise – Phil Collins (1989)

Sir, can you help me? It’s cold and I’ve nowhere to sleep

A protest song about the plight of homelessness in the world. It was a huge shift from Collins’ earlier pop and dance songs.

Stranger in Moscow – Michael Jackson (1995)

“How does it feel, When you’re alone, And you’re cold inside?”

This is a really powerful film clip and such a stark contrast to the mega production style of Jackson’s other music videos. Black and white in its simple best. The use of slow motion was a breakthrough. Perhaps my favourite Michael Jackson song closely followed by Human Nature. Written at a time when Jackson was on his Dangerous tour in Russia with a growing media frenzy over abuse allegations forming in the background.

I’ll Stand By You – The Pretenders (1994)

Won’t let nobody hurt you, I’ll stand by you

Iris – Goo Goo Dolls (1998)

When everything’s made to be broken, I just want you to know who I am.

Could this be the most overplayed song on Australian FM radio in the last 15 years?!

Mad World – Gary Jules (2001)

Bright and early for the daily races, going no where, going no where

https://www.youtube.com/watch?v=4N3N1MlvVc4

This is a cover version of the 1982 original by Tears for Fears. This version from the film Donnie Darko is stripped bare and missing the synth and pop of the 80’s version.

Candle in the Wind – Elton John

Originally written about Marilyn Monroe, this song was re purposed after the death of Princess Diana. It was supposed to be a new song but it turned out to be a misunderstanding by John’s long time song writer Bernie Taupin who rewrote the lyrics to the same melody. I’ve heard the original live – twice, but John has insisted never to sing the Diana version again. Ignore the video description, its definitely not from 2007. I was at that concert at the Sydney Entertainment Centre and he wasn’t dressed like that! Judging by the hair and clothes of the audience, I’m guessing this is the late 80s??

The image for this post is from the article: Images of The Great Ocean Road Victoria – 12 Apostles, London Arch, Port Campbell