Heartbreaking Songs

To continue on yesterday’s heartbreaking love songs, today I thought I would talk about ALL heartbreaking songs. I was 100% blind to heartbreak before my first year of college, but I did know about the emotion of sad. So at least I knew about sad- one of the emotions part of heartbreak. Heartbreak is basically a more devastating form of sad. What are the other emotions associated with heartbreak? The ones I have found are anger, guilt, and loneliness among others. Heartbreak can hit you like a pile of breaks and can reduce you to tears. So now here is a list of the heartbreaking musical theatre songs.

  1. I’m Not That Girl 
  2. On My Own 
  3. I Dreamed a Dream 
  4. Come to Me 
  5. Empty Chairs at Empty Tables 
  6. Drink With Me 
  7. A Little Fall of Rain 
  8. Bring Him Home
  9. All I Ask Of You (Reprise)
  10. Wishing You Were Somehow Here Again 
  11. If I Can’t Love Her 
  12. If I Can’t Love Her (Reprise) 
  13. Evermore 
  14. Endless Night 
  15. Letter From the Refuge
  16. This Nearly Was Mine 
  17. Somewhere
  18. Will I
  19. Your Eyes 
  20. Without You 
  21. Memory
  22. As Long As He Needs Me

These heartbreaking songs come from a number of musicals- Wicked, Newsies, Les Mis, Lion King, West Side Story, Beauty and the Beast, Rent, and Cats. Some of these songs are more devastating than others. Some of them hit me harder than others. Some hit me like a pile of bricks, and some don’t. Some of them make me tear up while others don’t.  Heartbreak is one of the most beautiful emotions in musical theatre and one of the strongest. 

Heartbreaking Love Songs

If a musical theatre song is both a love and sad song, it will ALWAYS be heartbreaking. That is always the truth- that’s for sure. These songs can be ironic or non-ironic. Those songs fall under unrequited love songs, breakup songs, or if the plot is a tragic love story. What are examples of these songs? Below I will list some of those songs. 

  1. I’m Not That Girl/ I’m Not That Girl (Reprise)
  2. On My Own 
  3. Somewhere 
  4. As Long As He Needs Me 
  5. This Nearly Was Mine 
  6. If I Can’t Love Her/ If I Can’t Love Her (Reprise) 
  7. Evermore
  8. All I Ask Of You (Reprise) 

I’m Not That Girl was the FIRST heartbreaking love song I was emotionally connected to, but was sad in the beginning. I never called I’m Not That Girl a sad love song- I never combined emotions together- I called it sad. On My Own, just like I’m Not That Girl, began as a sad song, but after a year I realized it was heartbreaking- On My Own was key to realizing I’m Not That Girl was heartbreaking. As a matter of fact, On My Own made me realize all sad love songs were heartbreaking. The heartbreaking love songs have a combination of emotions- they can be home to sad, anger, and loneliness: it depends on the song and the actor and actress who is playing the character. Some of those heartbreaking love songs are much more heartbreaking than others: for instance, On My Own is more heartbreaking than I’m Not That Girl. 


It sounds crazy how some of them are ironic- that means the love situation improves in the end or you don’t expect the character to sing it. I’m Not That Girl is the best example- after all the unrequited love shifts from Elphaba to Glinda, which is why the song is sung twice. In addition, the spell gets broken in Beauty and the Beast, which makes If I Can’t Love Her/ If I Can’t Love Her (Reprise), and Evermore ironic. The same situation happens with This Nearly Was Mine because Nellie goes back to Emelie in the end. 

Non ironic- that means the situation NEVER improves in the end. That would mean that character might have unrequited love the entire time. In Les Mis, Eponine has unrequited love for Marius till the end of her journey in Les Mis- she does have a tragic ending, but at the same time, her fate is touching and moving and is home to joy. Eponine’s fate is death, but she gets to die in the arms of Marius after getting shot- that is where the joy comes from. So On My Own is not ironic at all. So the heartbreaking love songs are both ironic and non-ironic. 

The heartbreaking love songs are some of the most beautiful songs in musical theatre. They are fragile, vulnerable, and some of them are home to innocence. It just depends on the character and how much they love the person they are in love with at that point in the story. 

Parallels that Exist in Musicals

These sort of things exist in the musical world. They are called parallels. What are some examples?

Wicked/ Les Mis

–  Elphaba/ Eponine- both have broken family lives, taken advantage of, part of a love triangle and deal with unrequited love (however the result is different)

-“On My Own”/ “I’m Not That Girl”- while on the topic of Eponine and Elphaba, I want to say the parallel between these two songs. Both are unrequited love songs. “On My Own” helped me understand “I’m Not That Girl” was a heartbreaking song.

– Fiyero/ Enjolras- this is weird. I don’t get it- for some reason, I think there might be a parallel between these two characters. Three of my Enjolras’ have played Fiyero either before or after they played Enjolras.


Les Mis/ Newsies

Newsies/ Friends of the ABC- they both share a similar brotherly love, and have a passion and hope for a cause they truly believe in

Jack Kelly/ Enjolras- they both are leaders of they group they are part of, but what they care about the most is different.


Wicked/ Frozen 

Elphaba/ Elsa- both girls are misunderstood, believed to be monsters, and have powers they don’t know how to control

Glinda/ Anna- they both are outgoing and funny

Friendship/ Sisterhood- I see the center core of each storyline being quite similar

“Let it Go”/ “Defying Gravity”- I feel like these songs are very similar in many ways

  • I wonder if these parallels are why I was drawn to Frozen as much as I was. After all Wicked sparked my love for musicals


Les Mis/ Cats 

“I Dreamed a Dream”/ “Memory”- both songs reflect on the past and how worse Fantine’s and Grizzabella’s life has gotten. Just like how “On My Own” helped “I’m Not That Girl”, “I Dreamed a Dream” made me realize “Memory” was a heartbreaking song.


What are other parallels? I think musicals do help you understand parts of other musicals at times.

Favorite Female Musical Characters: Part One

I recently talked about my favorite male musical characters. Now its the time for my favorite female characters. As a matter of fact, my favorite musical character is female and I will identify which she is. So here is my list of favorite female characters.

  1. Elphaba- Favorite
  2. Glinda
  3. Eponine
  4. Young Cosette
  5. Fantine
  6. Annie
  7. Grizabella
  8. Female Von Trapp Children
  9. Christine
  10. Mimi
  11. Belle
  12. Katherine
  13. Maria- Sound of Music
  14. Anna- King and I
  15. Audrey

These are my favorite female characters I can speak of right now. The next post will go into some of these characters more into detail and explain why I love them. About the the last two, they are two characters I love, but are not from musicals I love.

What Makes a Musical Character Complex?

Just like there are complex and simple musical plots, there are also simple and complex characters. But what exactly makes a character complex?

It was Wicked that made me start to understand the complexity and emotional side of musicals. Elphaba and Glinda were the first two characters I was able to call complex especially Elphaba.

I think a complex character has a lot to them. They tend to have some kind of inner conflict in their lives. There tends to be a lot to them and feel so well-rounded and feel well real to me. They are characters who tend to express negative emotions due to all of the conflict that is  happening in their lives.

Some memorable complex musical characters include Elphaba, Glinda,  Eponine, Javert, Jean Valjean, Fiyero (doesn’t seem complex, but now he does), Jack Kelly, Grizabella (yes I just included a cat) and yes there are more, but just can’t think of them at this moment.

Possible Spoilers:

Complex characters are the ones that are more fascinating. The complex characters are always in complex plots. Some of these characters don’t seem complex, but they are. Grizabella might seem simple in a way because she is a cat, but still she is complex. That is due to the fact that she is a heartbreaking and tragic character and has to deal with a lot of conflict struggling to be welcomed back into the Jellicle tribe when she came back.

Elphaba is complex in many ways. She has this incredible relatable nature and there is a lot to this character. I keep on being surprised that I keep on adding things to this character. She deals with a lot of conflict and has to face serious discrimination. She is smart, determined, unique, talkative, big-hearted and believes in equality and staying true to herself. The most important part of Elphaba is her relationship with Glinda.

Glinda is complex because at first she just seems pure comical, but in the second act, she goes through a lot of conflict because she has to hear rumors being spread about Elphaba. She even has to put up the fact that Fiyero has broken up with her and now she has unrequited love for Fiyero since he left her for Elphaba.


Fiyero is a character who doesn’t seem complex at all, but recently I began to realize the complexity of him. At first he is just this super rude and annoying Shiz student who doesn’t care about anything. His complexity comes from the love triangle. I keep on questioning him. Did he have a crush on Elphaba without realizing it? I saw signs of that possibility right before “I’m Not That Girl” and after the lion cub incident. Or did he know, but just didn’t tell anybody? Or was he only friends with Elphaba, but didn’t develop a crush or fall in love with her till later? I keep on questioning this because he eventually ends up with Elphaba. For me, I really think he had a crush on Elphaba in act I, but had no clue. He eventually realized it when he heard the rumors spread about Elphaba and could not believe Glinda was supporting all of this and so he decided to break up with her.


Jack Kelly is complex in my opinion. He is very well-rounded and in the musical, he has a hobby of drawing and is very talented at it. He is also the leader of the rest of the Newsies and is quite protective of his brothers especially Crutchie. He eventually goes through a lot of inner conflict after this big fight breaks out.


Jean Valjean is quite a complex character. He is the main character of Les Mis. He has to live his life as an ex-convict. He faces many moral dilemmas. He does his best to live by the example the bishop taught him. There is just so much to him. It must be challenging being an ex-convict and having to raise Cosette. True, Valjean shelters and protects Cosette a lot, but I don’t blame him. He is an ex-convict trying not to be sent back to jail because he knows Javert wants to.


Than there’s Javert. He was a character I honestly didn’t want to get to know. I am not an antagonistic fan person. I eventually noticed the complexity of him. I didn’t even care about him or even his fate. Before seeing the show in the West End, Javert didn’t even matter. I saw three Javerts through the movie, 25th anniversary concert film, and the community college, but none of them made me care about Javert. In the West End, I feel like I finally saw Javert for the first time and I finally cared for him during the suicide scene. Javert only sees the world in black and white and is incapable of showing mercy, love, or forgiveness. His main focus it to recapture Valjean. He takes his job to the extreme and follows the law too strictly.


Eponine is another complex character in Les Mis. You first meet her in 1823 when she was just eight. Through the way the Thenardiers treat Cosette and through realizing they are pickpockets during “Castle on a Cloud” and “Master of the House”, you get an idea of the environment she is going to be growing up in.

Her real complexity shows when she becomes a teenager at age 17. Her life has gotten even worse because at first she was spoiled and appeared to be loved by her parents. But you soon realized that is not even true. She was raised to be a criminal and she is horribly abused, neglected, and lonely. But she is brave despite what she has deal with everyday. You got to understand Eponine’s life outside of Marius to understand why she loves him so much. He was the only source of light in her miserable life and that is a huge reason why she loves him. Yes, she had unrequited love for him, but she still shows true love and would do anything for him. Even though she knows Marius will never be hers, she continues to love him till the end of her story.


In your opinion, what makes a musical character complex?