Best Melancholy Songs

Melancholy songs are fascinating. They create a nostalgic mood and a setting for experiencing unique emotions. If they don’t appeal to the listener, they run the risk of sounding too slow and boring, but if the listener establishes an emotional connection, that melancholy and nostalgia can be a rich cathartic experience.

Let’s explore a few of the top melancholy songs that accomplish this best.

Midnight Train by Bulat Okudzhava, Translated by Alex Genadinik

This is one of the most popular and poetic Russian songs of the 20th century. It has a wonderful melody and touching lyrics that reach deep into one’s heart and consciousness. So when I translated this song to English, I had to rewrite the lyrics to make sure that they still transmit the beauty of the original. Here is a page with all of Bular Okudzhava’s songs I translated into English, and here is a page with song lyrics of this song.

Over The Rainbow Performed by Eva Cassidy

The original Over The Rainbow song only had some melancholy moments, but Eva’s performance is all nostalgia. It’s one of the best ever performances of Over The Rainbow, and I personally can’t get enough.

Brothers In Arms by Dire Straits

This song’s unusually slow tempo fosters a somber and reflective atmosphere. This is a song about war. When you combine that with the sad subject of the song, that creates a feeling of quiet melancholy in the listener.

While My Guitar Gently Weeps by The Beatles

There are many great things about this song. Its poetic lyrics convey a poignant blend of emotion and melancholy. Even before listening to this song, the title already creates a sad feeling by use of a masterfully crafted metaphor.

Metaphors create vivid imagery in song lyrics that are more effective than hundreds of descriptive words. Great metaphors are present in many of the best songs. You can explore that further in my post about some of the most poetic songs, and a post about songs with the most interesting metaphors.

A weeping guitar is one of the most melancholy and nostalgic metaphors in all of music. It’s potent and pretty at the same time.

Wind Of Sighs by Alex Genadinik

This song is inspired by both philosophy and Shakespeare. Here is a full analysis of this dreamy and intimate song.

The wind of sighs is a reference to Shakespeare’s quote: “Love is a smoke made with the fume of sighs.”

This philosophical song explores the definition of beauty, a question pondered since the times of Socrates. This song creates its own definition: beauty is that which inspires. That’s attributed to the heroine of this song who inspires, but herself isn’t happy.

Everybody Hurts by R.E.M

The arpeggiating instrumentation evokes a deeply sorrowful mood, and the lyrics of “everybody hurts” combined with the mournful expression of the vocalist create a shared nostalgic and empathetic feeling.

Mad World by Gary Jules

This is another slow song that creates a melancholy setting.

This lyric captures the sad and melancholy feel of this song: “The dreams that are dying were my very-very best.”

1979 by the Smashing Pumpkins

This is another nostalgic song about looking back at the journey of life.

Piano Man by Billy Joel

Piano Man doesn’t have a particularly nostalgic sound to it, but the lyrics tell a story about seemingly incomplete characters who are somewhere in the middle of life. They are neither successful nor particularly trying to succeed. They are just there, somewhat incomplete.

Landslide by Fleetwood Mac

This is simply one of the best songs ever. It’s just perfect. It makes almost all the lists of my best songs. It’s emotional even before the listener fully comprehends what the song is about. In fact, a part of the magic of this song is that the listener doesn’t need to know the backstory of this song in order to feel what’s most important about it – the fleetingness of time and the moments in life that are further and further in the rearview mirror that we feel are unfinished.

Guardians Of Souls by Alex Genadinik

This is a song about a tough period in my life during which I felt alone, and what gave me a feeling of belonging are the poets and musicians who created beautiful works for me to consume, and find inspiration. Here is the page with longer analysis and lyrics for this tribute song about poets, musicians, and artists.

Old Man by Neil Young

Neil sings this song in a weeping tone, and the tempo of this song is quite slow. Perhaps the most nostalgic part of this song is the lyrics in the chorus: “old man, look at my eyes, I’m a lot like you.” This contrast between the old and the young man who are not too different in personality, life situation, and perhaps time lapse is a nostalgic thought and fear that we all share.

Country Roads by John Denver

What can be more nostalgic than traveling the backroads to where you grew up and seeing all the beauty of the timeless nature and the culture of the people who live there.

Heart of Gold by Neil Young

Many people think that this song is about Neil Young is about him searching for someone with a heart of gold, and that search is a relatable one for many people. But this song is really about the search for a heart of gold in himself that is also a journey.

Actually, many of Neil Young’s songs are very nostalgic. Even the more upbeat song Hey Hey, My My is about the dying of Rock And Roll, which is a sad thing to look back at.

How Long Will I Love You by Ellie Goulding

This song is so gentle. It has a mostly positive message, but the singer’s almost trembling voice tells a story of doubt. The melody in this song is one of the prettiest, enhancing its gentle and heartfelt message.

What Was It All For by Alex Genadinik

This is a sad breakup song about a relationship that could have been beautiful, but didn’t turn out that way. The lyrics are quite poetic. They start with “Whisper like a gentle stream. Carry me into your dream.” The song ends with “You whispered like a gentle stream. Now I’m a broken dream.”

Here is a page with full lyrics of this melancholy song. If you like sad love songs, I actually keep a full page with such songs here.

More Songs With Poetry

If you like poetic songs that evoke emotions, I do too, and I created a poetry book with songs to harness it in one place. You can read the poetry while listening to songs that contain those poems. Here is a page to learn more about my poetry book.