Top 10 Saddest Broadway Love Songs
#10: “I’m Not That Girl” “Wicked”
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Ever woken up from a dream and suddenly realized you can’t have what you want most? This song captures that sentiment to a T. Green with envy, Elphaba conceals her feelings as she remembers Fiyero, the man she’s developing feelings for, is pursuing her friend Galinda. With a melancholy melody and lonely lyrics, “I’m Not that Girl” will resonate with anyone who’s ever liked a person seemingly out of their reach. Just as the audience sheds a tear, it begins to rain upon Elphaba. The water doesn’t make her melt, as legend would lead some to believe, but this song will melt your heart. Although Fiyero does ultimately reciprocate Elphaba’s love, their romance comes at a cost, as Galinda realizes that she’s not that girl.
#9: “Mr. Cellophane” “Chicago”
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At first, “Mr. Cellophane” may not strike you as a love song in the traditional sense. When you get to the root of it, though, the song is about a meek man needing to feel something from anyone around him. The song seems upbeat, but during it, the dedicated Amos finds out his incarcerated wife Roxie is just using him. If even his own wife won’t pay attention to him, however, chances are nobody will ever notice Amos. He’s finally motivated to leave his wife upon realizing he’s not the father of her nonexistent child. All Amos wants is to be acknowledged, respected, and shown some basic human dignity.
#8: “There’s a Fine, Fine Line” “Avenue Q”
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You wouldn’t expect a musical with foul-mouthed puppets to bring the feels, but “Avenue Q” becomes surprisingly sentimental as Act I draws to a close. Feeling overwhelmed, Princeton tells Kate Monster that maybe they should hit the brakes. Princeton still wants to be friends - but this doesn’t comfort Kate. Belting out a powerful ballad, Kate contemplates if her relationship with Princeton was real or just a waste of time. “There’s a Fine, Fine Line” epitomizes that difficult moment when a couple realizes that they’re on different pages. She may be made of felt, but the rejection, vulnerability, and mixed signals Kate experiences couldn’t be more human.
#7: “If I Can’t Love Her” “Beauty and the Beast”
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This is a unique love song, as Belle and the Beast have yet to fall for each other. Actually, the Beast has virtually shattered his chances with Belle after scaring her away. Overwhelmed with regret, the Beast wonders if Belle could ever love a monster like him. What’s more, can the Beast find the humanity within himself to truly love another? All the Beast knows for sure is that Belle’s his last chance at redemption and he may have just lost her forever. Calling “The Phantom of the Opera” to mind, “If I Can't Love Her” is a haunting lament that encompasses why the Beast is such a tragic figure. Underneath his beastly exterior, there’s still a man seeking love, forgiveness, and a reason to live.
#6: “Satisfied” “Hamilton”
We can’t talk about “Satisfied” without discussing what precedes it: “Helpless.” Picking up when Alexander Hamilton first met Eliza Schuyler, “Helpless” chronicles this historical romance all the way to their wedding day. This upbeat love ballad is immediately followed by “Satisfied,” showing the previous song in another light. Turning back the clock and the stage, we return to the night that Alexander met Eliza, who attended the ball with her sister Angelica. We see that Angelica was also quite taken with Alexander, but takes her feelings out of the equation in favour of duty to her station - and her sister’s happiness. Angelica is thus forced to hold her tongue while toasting the happy couple, knowing she’ll never be satisfied. Love and heartbreak are truly different sides of the same coin.
#5: “Losing My Mind” “Follies”
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“Losing My Mind” almost starts off on an uplifting note, as if the sun is rising on a bright new day. As night begins to fall, however, we come to understand just how empty Sally Durant Plummer’s days are. Despite being almost 50, Sally beams with life. In many respects, the youthful Sally is trapped in the past, chasing a man she’ll never have. Although she’s married to Buddy, it’s Ben who consumes all of Sally’s thoughts. Sally obsesses over Ben to the point that she begins to question her own sanity, all while clinging to a relationship that’s been over for some time. This number puts the torch in torch song, setting Sally’s heart ablaze with fiery feelings of unrequited love.
#4: “I Don’t Know How to Love Him” “Jesus Christ Superstar”
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Mary Magdalene has made a living selling her body for money, never knowing the meaning of true love or seeing the true worth within herself. This all changes after she meets Jesus Christ, who doesn’t see Mary as a prostitute, but as a human being who deserves to be treated with the same affection as all of God’s children. As Jesus sleeps one night, Mary comes to terms with the fact that she loves him, which scares her intensely. Mary’s had so many meaningless relationships that she isn’t sure how to love anybody, let alone the Messiah. This tender ballad embodies all of the confusion and fear that love can summon, leaving Mary to consider if she should run from her feelings or embrace them.
#3: “I’ll Cover You (Reprise)” “Rent”
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“I’ll Cover You” demonstrates how one song can be interpreted in multiple ways. When we first hear the song, it’s a joyous duet shared between lovers Angel and Collins. Although AIDS and poverty have made life difficult for them, this couple has nonetheless built a happy home together. The audience couldn’t possibly be more elated listening to this cheerful tune, but the reprise comes at the musical’s most tragic moment. Angel has abruptly passed away, leaving the king without his castle. Suddenly, the lyrics take on a whole new meaning as Angel’s heart expires and Collins covers the love of his life. In a heartbeat, a delightful song can turn into a devastating one, and the most spirited person alive can become a literal angel.
#2: “Somewhere” “West Side Story”
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“West Side Story” hasn’t lost its relevance in a world where prejudice continues to drive people apart. Coming from different ethnic backgrounds, Tony and Maria fall in love against the backdrop of a gang war. Although they’re initially convinced that love will prevail, reality sinks in when loved ones get caught in the crossfire of hate. It becomes clear to Tony and Maria that they can no longer remain in this environment. Through a quietly poignant duet, the couple dreams of a place where they can find peace and rewrite the wrongs of the past. They may still be living in a fantasy, but for a brief moment, the two find comfort in each other and the hope of moving somewhere better. The tragedy is all the more all-consuming knowing the unfortunate fate the pair meets. Before we get to our top pick, here are a few honorable mentions: “Loving You” “Passion” “As Long as He Needs Me” “Oliver!” “Unworthy of Your Love” “Assassins” “I Know the Truth” “Aida” “Not a Day Goes By” “Merrily We Roll Along”
#1: “On My Own” “Les Misérables”
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“I Dreamed a Dream” may be a tear-jerker, but “On My Own” is Broadway’s definitive song about unrequited love. Éponine’s one of the most complex and tragic figures in “Les Misérables,” pining after a man whose heart belongs to another. While she knows that Marius will never be hers, as she walks through the streets of Paris, Éponine can’t help but imagine what could’ve been. As the song gains momentum, her emotions become angrier, and it doesn’t take long for Éponine’s parade to be rained upon, and she reminds herself that her love is one-sided. Overflowing with disappointment and heartache, this passionate song will speak to anyone who’s ever hidden their feelings from the one they love most.
