Top 10 Best Stephen Sondheim Songs
#10: “Not a Day Goes By” “Merrily We Roll Along”
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“Not a Day Goes By” will simultaneously melt and break your heart, one of Sondheim’s trademarks. As Act 1 nears its end, so does Frank and Beth’s marriage. Beth can’t forgive Frank following his affair with Gussie, but that doesn’t mean they’ve fallen out of love. Although Frank performed this song in the original Broadway production, it was reworked as a solo for Beth in the off-Broadway revival. Whoever sings it, the song will resonate with any couple that’s broken up, despite still caring deeply for one another. The lyrics are full of frustration, but the melody possesses a nostalgic sentiment, perfectly fitting the singer’s conflicted feelings. Even if Beth leaves Frank, they’ll occupy each other’s thoughts every day until the end of time.
#9: “Send in the Clowns” “A Little Night Music”
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This musical follows a man, his virginal wife, his old flame, her lover, and his wife, all of whom collide for “A Weekend in the Country.” “A Little Night Music” is a classic farce, but it’s not all laughs. Although one might assume it’s a happy song, “Send in the Clowns” is a tragic tune masked by a comical title. Having been rejected by Fredrik, Desiree reflects on the foolish choices that led her there. There’s an old saying in the theatre that when the show goes downhill, send in the clowns. If Desiree’s life is a show, then this would be an ideal time to lighten the mood with a joke. Not even clown makeup can conceal the doleful song in Desiree’s heart, however.
#8: “No One Is Alone” “Into the Woods”
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It centers on fairy tales, but “Into the Woods” doesn’t wrap up in happily-ever-after fashion. Many characters meet dire fates while the survivors are left to pick up the pieces. What gives the remaining characters a glimmer of hope is that they don’t have to endure these dark times alone. The Baker, Cinderella, Little Red, and Jack find that they’ve all made selfish choices. By coming together and learning from each other’s mistakes, though, perhaps they can make a better world for children to inherit. Whether you’re going through a personal tragedy or something on a wider scale, it’s easy to feel isolated. This bittersweet tune reminds us that no one is alone, and unity is the first step towards a happier ending.
#7: “Rose’s Turn” “Gypsy”
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Mamma Rose’s world revolves around molding her daughters into stars. Rose’s dream was never about June and Louise, however. This stage mother was forcing them to live out her own dream of fame and she’s seemingly alienated everyone in the process. The spotlight has always belonged to Rose, but now she’s truly taking center stage for a show-stopping solo. Rose beams with confidence as she proclaims to the audience that she’s got it. She’s ultimately singing to an empty theater, however, slowly pulling her back down to reality. Sondheim’s lyrics and Jule Styne’s music bring out Rose’s passion, regret, and bitter broken dreams. It’s a triumphant song with melancholic undertones that leave the audience to wonder if everything is really coming up roses.
#6: “Somewhere” “West Side Story”
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Caught in the middle of two rival gangs, Tony and Maria aren’t sure how they can be together given all of the hate that surrounds them. They thus decide to escape from the Upper West Side and find somewhere else for their love to flourish. Sondheim’s uplifting lyrics are perfectly complemented by Leonard Bernstein’s soothing melody as the star-crossed lovers long for peace, forgiveness, and acceptance. Although their love story ends in woe, “Somewhere” remains a beacon of inspiration that guides its listeners to a better tomorrow. The place Tony and Maria sing about could exist anywhere if people put their prejudices aside. Unfortunately, it sometimes takes a tragedy to make people open their ears and their minds.
#5: “Epiphany” “Sweeney Todd: The Demon Barber of Fleet Street”
“Sweeney Todd” is easily the most haunting musical Sondheim has ever cooked up. “Not While I’m Around” is an especially eerie duet as two people sing about protecting the ones they love most… by any means necessary. “Epiphany” is arguably the most crucial song, though, as it sees Sweeney Todd fully become the demon barber of Fleet Street. Having missed his shot at the judge, the vengeful Todd is no longer satisfied with slitting his throat. He plans to give everyone in London, the rich and poor alike, a close shave. Like the best villain songs, “Epiphany” is menacing while also getting the audience pumped. Mrs. Lovett has an epiphany as well, realizing what’s been missing from her meat pies… [A Little Priest]
#4: “Getting Married Today” “Company”
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Ironically, “Getting Married Today” is one song that you probably wouldn’t want to play at your own wedding, but any Broadway fan should have it on their playlist. This patter song authentically captures the panicked sensation of getting cold feet on the big day. The hyper music makes you feel the butterflies swarming around in Amy’s stomach as she thinks of all the reasons not to marry Paul. Sondheim’s witty lyrics fly at the audience a mile a minute with little if any room to pause. To master a song as fast-tempo as this, you need the timing of a comedian and the speedy delivery of an auctioneer. If executed properly, this song will leave the audience breathless before even making it down the aisle.
#3: “Losing My Mind” “Follies”
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Sometimes love just doesn’t make sense, which can drive a person insane. Such is the case for Sally, a showgirl looking back on her relationship with Ben and the future they can’t have together. Although Sally knows that her feelings are one-sided, she can’t get Ben out of her head. Sondheim’s lyrics and music are so calming at first, but it doesn’t take long for the song to spiral into despair and loneliness. You can sense that Sally is putting up a tough front, but on the inside, her heart is at war with her mind. “I’m Still Here” also carries a nostalgic note as aging film star Carlotta reminisces about her colorful career. Yet, “Losing My Mind” is the more personal and poignant number.
#2: “Sunday” “Sunday in the Park with George”
This musical depicts Georges Seurat as an artist who lives in his paintings, neglecting the real world around him. This shines through in the number “Finishing the Hat,” as George continues to put his work before his loved ones. The song that best exemplifies George’s creative genius and obsession, though, would have to be the Act 1 finale. “Sunday” finds George in the park where his subjects are running amuck. George freezes the moment in time, painting a portrait in his head as the ensemble sings in harmony. As the pieces start falling into place, the melody becomes more relaxing than a stroll through the park. Once the song reaches its climax, you can feel George’s vision come into fruition and it’s picture-perfect. Before we unveil our top pick, here are a few honorable mentions. “Someone in a Tree” “Pacific Overtures” “Comedy Tonight” “A Funny Thing Happened on the Way to the Forum” “The Ballad of Booth” “Assassins” “Take Me to the World” “Evening Primrose” “Loving You” “Passion”
#1: “Being Alive” “Company”
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In so few words, “Company” is about finding what’s most important in life. Some folks go through life dwelling on insignificant things, as demonstrated through the sarcastic song “The Ladies Who Lunch.” For Robert, he’s spent more than three decades fearing the concept of marriage, content with having a group of close friends. Robert focuses on all the downsides of commitment, repeatedly asking the question, “What do you get?” The more thought he gives the question, Robert finds that he may get more than he initially assumed. This spellbinding song speaks to anyone who’s ever been afraid to pursue something that always seemed out of reach. It may not be perfect, but the journey - be it full of highs or lows - is part of being alive.
