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Ask the Mary Sues: Our Favorite Stephen Sondheim Songs

We look back at Sondheim's unparalleled legacy of music.

Stephen Sondheim being Stephen Sondheim

When composer and lyricist Stephen Sondheim passed away last week at 91 years old, he left a monumental legacy that few artists can rival. Sondheim’s body of work reshaped American musical theater, pushing the boundaries of the genre and exploring new worlds within the art form. Fans from around the globe have paid homage to Sondheim, as have the Broadway community. His death has had us all revisiting our favorite albums and numbers from his vast catalogue of work. Here are some of our favorite Sondheim numbers.

Rachel Leishman:

“Marry Me a Little” from Company is a beautiful look at life and love and this idea of marriage that so many of us have. It also explores how some of us have an inability to ever understand what the world and universe want from us in that department. Bobby doesn’t want to fully give himself away to love. He wants to be himself and happy, but he also doesn’t want to be alone, and this song is a perfect look at that weird balance while also breaking my heart into a million pieces. Truly any song from Company hurts by design. You’re supposed to be utterly wrecked by the time you get to “Being Alive” and while that might actually be his prettiest song (with also the exception of the entire cast recording of Sunday in the Park With George), I just love “Marry Me A Little” so much.

Chelsea Steiner:

Admittedly, I was going to write about the sublime “Ladies Who Lunch” from Company, but given the new West Side Story hitting theaters next week, I can’t not seize the opportunity to talk about “Gee Officer Krupke.” At the start of his career, Sondheim wrote the lyrics for Leonard Bernstein’s musical masterpiece, which would go on to be a staple of American theater. West Side Story is filled with fantastic numbers, but few are as darkly funny and aware as “Gee Officer Krupke.” What starts as a song mocking the inept local policeman turns into an indictment of law enforcement, the justice system, and social programs that continue to misunderstand and mistreat at-risk teens. Before the term “school to prison pipeline” was even invented, Sondheim artfully told a story of the ways in which the government and the adults in charge fail the youth on both a personal and societal level. Few numbers remain as timeless or as searing an indictment on how this country works.

Kaila Hale-Stern:

It’s almost impossible to choose a single song from my favorite Sondheim musical, the macabre masterpiece Sweeney Todd, but I think I have to go with “Epiphany” (Len Cariou/Angela Lansbury cast recording, natch). “Epiphany” is a song like no other, one man’s journey through every conceivable emotion, a feat of lyricism, scoring, and stunning vocals that take on hatred and anguish in equal measure. If you don’t get shivers every single time Sweeney sings, “And my Lucy lies in ashes/And I’ll never see my girl again/But the work waits!/I’m alive at last!/and I’m full of joy!” I don’t know what to tell you about your life and your choices.

The split pathos of this song—of Sweeney losing his chance at vengeance, banishing all hope, resolving to murder, and finally leaving behind everything that he loved—there’s nothing like it in any musical anywhere. And like much of Sweeney Todd, “Epiphany” teaches a sharper awareness of human nature than you’ll find in college philosophy classes: “Because in all of the whole human race/Mrs. Lovett, there are two kinds of men and only two/There’s the one staying put in his proper place/And the one with his foot in the other one’s face.”

Alyssa Shotwell:

“God, That’s Good!” From Sweeney Todd both serves as a musical callback to another one of my favorite songs “Pirelli’s Miracle Elixir” and plays out into a fun busy scene. Little spunky vocal kids that are kinda too entrepreneurial out of desperation are entertaining and a very sad. Tobias and Mrs.Lovett peak here, and I love their found family, while it lasts.

Princess Weekes:


What’s your favorite Sondheim number? Let us know in the comments!

(image: Thos Robinson/Getty Images for The New Yorker)

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Chelsea was born and raised in New Orleans, which explains her affinity for cheesy grits and Britney Spears. An pop culture journalist since 2012, her work has appeared on Autostraddle, AfterEllen, and more. Her beats include queer popular culture, film, television, republican clownery, and the unwavering belief that 'The Long Kiss Goodnight' is the greatest movie ever made. She currently resides in sunny Los Angeles, with her husband, 2 sons, and one poorly behaved rescue dog. She is a former roller derby girl and a black belt in Judo, so she is not to be trifled with. She loves the word “Jewess” and wishes more people used it to describe her.