Top 20 Hauntingly Beautiful Songs in Musicals

Jonathan Larson’s semi-autobiographical musical premiered Off-Broadway several years after his premature death. He left his mark with “Rent,” but “tick, tick... BOOM!” is a personal piece about his attempts to make a name for himself in the artform he loved. His character Jon’s solo near the end of the show charts his obsession with trying to get better. Given all he’s had to sacrifice, he wonders if he’s cut out for this career after all. “Over and over ‘til we get it right,” he repeats throughout the song. “Why”’s repetitive structure keeps winding up and righting itself as it starts to go off track, mirroring the composer’s approach to his art, career, and ultimately, his life.

A lot of the classic musical love songs are naive and pretty. The title song from “The Light in the Piazza” is so full of happiness it feels dangerous, and therein lies its power. Clara, the character who sings it, has fallen in love with Fabrizio, a young Italian man, much to the dismay of her overprotective mother. The way she describes her feelings sounds like a person who’s sure she’s flying too close to the sun and doesn’t care. Composer and lyricist Adam Guettel’s music is elegant but frantic. Certain sections sound like individual instruments spinning out, following their own emotional tangents before coming back together, and it’s breathtaking.

This Sondheim musical is inspired by the life of Georges Seurat and the creation of his painting, “A Sunday Afternoon on the Island of La Grande Jatte.” “Sunday” is a song that first appears at the end of Act I, as George brings harmony to the disparate parts of his painting. The ringing of the ensemble’s voices sounds like waves of endless music, and it’s a gorgeous piece that takes us into intermission feeling moved. The reprise, for its part, comes at the very end of the show, and is just as hauntingly beautiful, sending audiences back into the real world in inspiring fashion. Both versions of the song speak to the power of art, and are sure to echo for many generations to appreciate.

It may not be “Hamilton,” but this often overlooked musical about the Second Continental Congress features some haunting and foreboding moments. Throughout the show, an army courier briefly appears to bring updates from the battlefield. In the second act, he describes how his two best friends died on the same day at Lexington. “Momma Look Sharp” is his one and only number. The lyrics describe a young soldier calling out for his mother as he lays dying in the grass. We’ve spent lots of the musical listening to the congressmen battle and complain about the heat in Philadelphia, but it’s the first time the reality of the war comes crashing in on us.

Reviving the old-fashioned, Big Band sound of the 1940s, this post-World War II musical finds a band made up of veterans trying to make it big. The bandleader and pianist, Donny Novitski, enters them into a national competition. However, once they win the state competition, they realize they’ll have to pay their way to the national finals. Short on cash, Donny tries to unite his bandmates through “Right This Way”. The song’s optimism and brass-and-drums are nothing short of powerful. He’s not a man who feels entitled to anything, but he knows they deserve to be recognized for their talent, if not everything they gave up. It’s not the only breathtaking number, either, as we later feel the soldiers’ repressed pain leftover from the war.

Given the title, it’s not surprising how many characters in this epic musical are suffering. Its most famous and spine-tingling songs deal with lost hopes, unrequited love, survivor’s guilt, and revolution. “Bring Him Home” is like a prayer in musical form. Self-sacrificing Jean Valjean has camped out with a group of young revolutionaries to protect Marius, the man his adoptive daughter loves. As night falls and their chances of survival dim, Valjean asks a higher power to protect Marius. Its religious overtones and allusions to “home” make it a number that has implications that stretch far beyond the musical’s plot.

The population of Gander, Newfoundland is suddenly doubled when 38 airplanes are forced to land there when the American airspace is suddenly closed without explanation. Chaos ensues until everyone learns of the 9/11 attacks. This brief, but heartbreaking song captures the moment the American passengers catch up with the rest of the world. Throughout, they can only watch while they worry for their loved ones and pray for the missing, the dead, and the grieving. What the musical does so well is capture the confusion of that time, which can be forgotten some two decades on, now that the details have become known.

Anthony is a sailor who, despite having seen the world, feels most at home in London. When he sees Johanna, the lovely ward of the sadistic Judge Turpin, he decides he loves her. Seeing her as something of a caged bird, he vows to steal her away. His promises that he’ll always be beside her, in the dark, buried in her hair, do give stalker vibes if you look at it through that lens. But even assuming the purest intentions, Johanna is the Judge’s prisoner and Anthony’s love song for her is also a promise of rescue.

As the characters near the end of their journey, the Baker and Cinderella comfort their young companions, and reckon with what they’ve learned about loss, consequences, and forgiveness. It’s a sweet song for a hard truth. They sing about remaining good in spite of the world, even as they struggle to make sense of their own sadness. There’s almost a sense they’re making the words up as they go along, chasing the truth as it comes to them. Weaving in motifs from other melodies in the show, this climactic song is the culmination of the musical’s lessons. It is a fairy tale after all.

Jenna is a waitress at a small diner whose love of pie-making is all she has to keep her going. When she becomes pregnant with her abusive husband’s baby, she saves up enough money to leave him, only for him to steal it and leave her with nothing. The song that composer-lyricist Sara Bareilles wrote for the moment is a powerhouse ballad that suits the character so perfectly. She mourns the person she used to be, imperfect as she was, and indirectly vows to become that person again. As hopeful as the story turns out to be, the song is such a journey it’s hard to not feel emotionally spent by the end of it.

There’s nothing quite like reflecting on an ex. Sung by Desiree, “Send in the Clowns” takes place during Act II, when she reflects back on an affair she had with Fredrick. Despite the fact that Fredrik was deeply in love with her, Desiree rejected him, and she now realizes that she loves him - but this time around, he rejects her. The clowns Desiree refers to are not actual clowns, but fools like herself. The song itself is written in a complex meter, which is one of the reasons it is so haunting - it sounds like a waltz. Desiree is also furious - she can’t outwardly express her anger, so she does what characters do in any musical - she sings about it.

Based on Alison Bechdel’s graphic novel “Fun Home”, this musical centers around Bechdel’s own coming out story and the complicated relationship she shared with her own closeted father, Bruce. Sung towards the end of the musical, this is the last conversation Alison has with her dad. She desperately tries to connect with her father while also revealing who she truly is. The song’s heartache lies in her father’s denial and how they never actually made a connection with each other. The song is even more heartbreaking considering the ending of the musical where it’s hinted that Bruce takes his own life.

Only a truly stormy partnership could serve as the inspiration for this haunting melody. “Time Heals Everything” is part of the musical “Mack and Mabel,” which centers around silent movie director Mack Sennett who transforms Mabel, a local waitress, into a “star.” Mabel develops feelings for Mack, but sadly, Mack puts his work before romance. “Time Heals Everything” is Mabel’s sorrow over how Mack treated her, but also her way of saying “I’ll get over him.” When it comes to heartbreak, we’re often told to give it time, and that’s exactly what Mabel is telling herself. The song is particularly haunting when you think about what ultimately happens to the character - she deals with substance use disorder, and by the time Mack tries to make it up to her, she’s passed away.

With lyrics by the late great Stephen Sondheim, “West Side Story” can be thought of as a modern retelling of the tragedy “Romeo & Juliet”, except that this version involves street gangs in New York City. “Somewhere” appears during different points of the musical, most notably when Maria sings the first few lines of the song after her true love, Tony, is shot. The melody actually borrows from Beethoven’s “Emperor Piano Concerto” and Tchaikovsky’s “Swan Lake,” which is why it’s so haunting. Tony and Maria’s longing to one day be together “somehow, someday, somewhere,” is sure to make you cry - especially since their dream never does come true.

“Ragtime”, which has still not been turned into a movie musical and needs to be, follows a series of characters as they navigate life at the turn of the 20th century in New York. Sung at the end of Act I, “Till We Reach That Day” takes place at the funeral of Sarah, a young Black woman who is beaten to death by the Secret Service. Her friends and family gather to mourn their sweet Sarah as well as express their anger at a system where Black lives do not matter. The powerful lyrics are still disturbingly relevant today and serve as a reminder that Black Lives do indeed Matter.

Imagine being so obsessed with your ex-lover that you slowly lose your mind over them. That’s the focus of the song “Losing My Mind” from the musical “Follies,” which focuses on the reunion of performers known as the Weismann’s Follies. Back in the day, Sally was in love with Ben, but he ended their relationship to marry her friend Phyllis. Sally married Buddy, but remained in love with Ben - even though he doesn’t love her - at least not in the same way. Dressed as a torch singer, Sally sings “Losing My Mind” about her longing and the fantasy world she has entered where Ben loves her. The song’s power lies in Sally’s obsession and her wondering whether or not Ben ever did actually love her.

Based on the opera “La Boheme” but set amongst the AIDS crisis in New York during the late ‘80s and early ‘90s, “Rent” has a soaring and inspirational first act that quickly dissolves into tragedy in the second. Tom Collins, a local gay professor, falls in love with the vivacious Angel. The pair’s relationship is one of the most heartwarming stories in the musical, and their upbeat duet, “I’ll Cover You” is an expression of their pure love. Sadly, their relationship becomes heartbreaking when Angel dies of AIDS. Collins reprises “I’ll Cover You” as he remembers the love he and Angel shared. The slowed down version is a reflection on how one person can truly make our lives magical.

Even before “Hamilton,” Lin-Manuel Miranda was emotionally destroying us with “In the Heights”. But “Hamilton” mixed numerous musical genres to create a spectacular retelling of one of America’s founding fathers. Amidst the rap battles is one song that provides a straightforward reflection on mourning through more simple instrumentation: “It’s Quiet Uptown.” Sung towards the end of the musical, “It’s Quiet Uptown” focuses on the unimaginable: a parent’s grief over their child’s death. Alexander Hamilton, who at this point in the musical has done his wife dirty on numerous occasions, begs for forgiveness as the two try to grapple with their grief. Although Eliza faces more grief in her life, she doesn’t let it get the best of her as she details her accomplishments in “Who Lives, Who Dies, Who Tells Your Story.”

The second musical from musical greats Rodgers and Hammerstein, “Carousel” isn’t exactly one of their more cheerful outings. Sung towards the end of the musical, “You’ll Never Walk Alone” is sung by Nettie to her cousin Julie, whose love, Billy, has just died in her arms. The song serves as the second act’s emotional peak and its themes center around hope and resilience. Over the years, numerous covers of “You’ll Never Walk Alone” have emerged, and it’s become the anthem for medical heroes during Covid. Theatrical performances of the number often use more simple musical arrangements, which allow the inspirational lyrics to shine through.

Before we unveil our top pick, here are a few honorable mentions.

“Memory,” “Cats”
Grizabella the Glamour Cat Makes Her Plea

“Neverland (Reprise),” “Finding Neverland”
Peter Pan Carries Sylvia Off to Neverland

“Lily’s Eyes,” “The Secret Garden”
Two Brothers Remember a Lost Love

“Maybe This Time,” “Cabaret”
A Cabaret Performer Hopes Her Luck Will Change

“Somewhere That’s Green,” “Little Shop of Horrors”
Audrey Dreams of a Different Life

We can all pretty much agree that the plot of “The Phantom of the Opera” - in which a mysterious masked musician who lurks in the bowels of the Paris Opera House, is obsessed with the beautiful soprano Christine - is just a little creepy. There are multiple hauntingly beautiful songs throughout this musical, including the painful lament Christine sings to her father in “Wishing You Were Somehow Here Again” , but “The Music of the Night” is definitely the most haunting. The Phantom seduces Christine with this song while also revealing his more sinister intentions. The song itself usually begins slowly, backed by only a few instruments before the rest of the orchestra joins in, ending in an unbelievable cresendo.