Favorite Heartbreaking Musical Songs

I once made a list of favorite sad musical songs. It included songs that are not heartbreaking, but just sad. All heartbreaking songs are sad, but not all sad songs are heartbreaking. I find the heartbreaking songs to be so much more beautiful, strong, fragile, and vulnerable than the songs that are just sad. Heartbreak is a deep level of sad, which has other negative emotions associated with it like loneliness and anger.

  1. On My Own- Les Mis
  2. I’m Not That Girl- Wicked
  3. I Dreamed a Dream- Les Mis
  4. A Little Fall of Rain- Les Mis
  5. Empty Chairs At Empty Tables- Les Mis
  6. Castle On A Cloud- Les Mis
  7. Come To Me/Fantine’s Death- Les Mis
  8. Memory- Cats
  9. Your Eyes- Rent
  10. One Song Glory-Rent
  11. Will I?- Rent
  12. I’ll Cover You (reprise)- Rent
  13. This Nearly Was Mine – South Pacific
  14. Wishing You Were Somehow Here Again- Phantom of the Opera
  15. Letter From The Refuge- written for the Tour of Newsies
  16. Somewhere- West Side Story
  17. If I Can’t Love Her- Beauty and the Beast

Possible Spoilers:

There was a time when songs like “I’m Not That Girl” were not interpreted as heartbreaking. I didn’t even know that emotion actually existed at the time. I didn’t fully know what it meant for a song to be heartbreaking. It was a heartbreaking musical that made me understand the negative emotions differently. “Les Mis” made me look at the negative emotions fresh and gave me a much clearer understanding of those emotions. While most musicals are happy, the sad musicals are just as essential as the happy musicals. When it comes to the negative emotions, I find something very special about feeling heartbroken. Heartbreak seems to be the main source of sad. I was actually quite surprised that some of these songs are death songs.


The most memorable death in musicals so far is the death of Eponine in Les Mis. There is just something touching about “A Little Fall of Rain”. She has been shot and her wound is fatal. While she is dying, she in the arms of Marius, a sweet and compassionate boy, who she falls in love with unrequitedly. Being in his arms at the time of her death is the happiest moment of her life. While this leaves Marius devastated, he stays brave for her and comforts her until she dies.


Sometimes I feel like heartbreak can be very hard to describe. Even that layer of sad is layered too. For instance, I understand that both “On My Own” and “I’m Not That Girl” are heartbreaking unrequited love songs. But “On My Own” is more heartbreaking than “I’m Not That Girl”. The thing with “I’m Not That Girl” is right before Elphaba sang this song, she just realized she loves Fiyero. But with “On My Own”, when it is sung by Eponine, she already has known she has loved Marius for some time now and she loves Marius a lot more than how much Elphaba loves Fiyero.


Some of these songs I had to revisit. Some I don’t quite remember if I was able to view them as sad the first time around. I had nearly forgotten about “Letter From the Refuge” when I saw Newsies in August. It was written for Crutchie, but when I found the song again and listened to it again, I recognized one line that I remembered from the stage show. That was the one moment that I had forgotten about, but so glad I was able to revisit the song. I It took a couple of listens to understand the song was heartbreaking. Being at the Refuge is rough on Crutchie because he has a bum leg, which makes him quite vulnerable there. I do remember at the beginning of Newsies, you learn of the special love that Jack has for Crutchie and was worried that he will end up in the refuge. Jack is very protective of Crutchie and when Cruthcie was arrested at the end of Act 1, this leaves a lot of inner conflict for Jack to handle, which almost caused him to give up on the strike.



Author: mphadventuregirl

I am a strong spiritual person who is a big fan of musicals. This blog deals with spirituality and musicals. I am finding that by writing about these, I am realizing I know more about each of them then I think I do. I hope you find my blog inspiring!

10 thoughts on “Favorite Heartbreaking Musical Songs”

    1. Crazy how much of this list are songs from Rent and Les Mis. So glad that heartbreak is part of the musical world. Having heartbreak in the mix made things so much more clearer. Clearly before Les Mis entered my life, I didn’t know what it meant for a song to be heartbreaking.

      Liked by 1 person

      1. Some of my all-time favorite musical characters have sung a heartbreaking song. Heartbreaking song have a bigger sense of fragility and vulnerability than a sad song that is not heartbreaking. Heartbreaking songs have been some of the most beautiful songs ever. Heartbreaking songs have been sung by heartbreaking characters or sung by characters that are not ultimately heartbreaking, but do face heartbreak at some stage in their life.


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