Top 10 Hauntingly Beautiful Songs in Musicals

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 - poor Mabel becomes a drug addict 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.

The Broadway hit, Hamilton, mixed numerous musical genres to create a spectacular retelling of one of America’s founding fathers: Alexander Hamilton. Amidst the rap battles is one song that relies on 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.” However, “It’s Quiet Uptown”’s power lies in its simplicity - most of the numbers in Hamilton rely on word play, rhymes, and double meanings, as it is a straightforward reflection on mourning.

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.

“No One Is Alone”, “Into the Woods”
We All Need This Reminder From Time to Time

“The Light in the Piazza” , “The Light in the Piazza”
The Sheer High Notes That Are Hit Will Send Shivers Down Your Spine

“Maybe This Time”, “Cabaret”
Simultaneously Hopeful & Desperate About Love

“Why” , “Tick, Tick... Boom!”
If You’ve Ever Wondered If the Sacrifices You’ve Made for Your Career Are Worth It, Then This Will Haunt You

“Johanna”, “Sweeney Todd: The Demon Barber of Fleet Street”
What Sounds Like a Sweet Love Song Turns Downright Creepy When You Listen Closely to the Lyrics

We can all pretty much agree that the plot of 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.