The 5 Saddest Songs From Musicals: Need a Good Cry?

While many popular musicals are known for their uplifting nature — filled to the brim with sunshine-and-rainbow narratives — others grab hold of your heart, yank it from your chest, throw it on the ground, stomp on it, and shove it back in…dejected and defeated. From Les Miserables to The Last Five Years, the saddest musical numbers are present in the classics and the modern musicals alike. 

Les Miserables Musical
The Final Performance of Broadway’s Long-Running Tony Award-Winning Musical ‘Les Miserables’ | Bruce Glikas/FilmMagic

While there are a plethora of painful, pitiful, and poignant numbers that ultimately lead to an “ugly cry,” this list will draw attention to five songs that send chills down the spine, leave tears swelling in your eyes, and carry the mind down a reflective (and often ravaged) road. 

5. ‘Not a Day Goes By’ from ‘Merrily We Roll Along’

Stephen Sondheim’s lyrics always convey a limitless depth of human understanding. And, he possesses the vocabulary needed to depict the nuances that separate our emotions. There is a difference between spite and anger, between disappointment and despondence. 

In Merrily We Roll Along, a woman sings of the man she will always love but can no longer stand across, as his affair has smudged their relationship. She cannot trust him, but she will continue to love him, she will “die day after day after day ‘til the days go by.” She will survive (not live) alone — yearning for the love he gave until the day she dies — yearning for the life they had before he tainted it. 

4. ‘I Miss the Mountains’ from ‘Next to Normal’ 

In Broadway’s Next to Normal, Alice Ripley portrays Diana: a woman with bipolar depression who sees her son, a boy who died when he was just a baby. Yet, he is now 18 years old, and she sees the teenager he “would have” become. 

After trying multiple medications and treatments (often to no avail), she stumbles upon one the mixture that “works —” one that numbs her pain. The downside: it numbs all of her emotional experiences. Here, she sings of “missing the mountains” that define life — the “highs and lows” that make us human and establish our identity. Here, she realizes that what she misses is her life. If this one doesn’t make you cry, especially if you watch Diana pour her medication into the toilet as she sings, nothing will. 

3. ‘I Dreamed a Dream’ from ‘Les Miserables’

“I had a dream my life would be…” Need we say more? Fantine sings of what never was, and what never can be — the love that came, and the night that swept him away. She had it all planned out, but “life has killed the dream [she] dreamed.”

Unfulfilled desires, unattainable happiness, forlorn, and at the mercy of those unkind and selfish, she imagines “what if.” The poignancy of the moment surprises audiences and Fantine herself. The song reaches a height of emotional pain — and Fantine’s voice and the music grow louder in tandem — before ending with a softness, representing the demoralization that has seized her existence, and the helplessness that has beat out the anger. 

2. ‘I’m Still Hurting’ from ‘The Last Five Years’

The Last Five Years tells the story of Jamie and Kathy — and the five-year marriage that brought them to utter bliss and complete emptiness. They were perfect, and then they weren’t. Here, Kathy sings about Jamie, who “is over and gone,” as she remains, left behind, “covered in scars [she] did nothing to earn.”

While love forged and lost would be enough to make this song sad, it’s Kathy’s realization that Jamie assumed he had “the right to decide” when they were done fighting — like he knew it was his call all along. All the lies, and all the pain… if Kathy could “hang them back on the wall,” maybe she would have seen how Jamie could be “so certain” that they had “no chance at all.”

1. ‘I’ll Cover You’ from ‘Rent’

Did you think Collins singing “I’ll Cover You” during Angel’s funeral in Rent would not top the list? He has lost the love of his life. And, as he stands beside his coffin, he wants to leave him with one last message: he will cover him. All he must do: pay him back in 1000 kisses. It’s reminiscent, yet also aware of a future that did not come to fruition — a life dream never fully reached, but always deeply understood.