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Top 10 Hardest Modern Broadway Songs to Sing

Top 10 Hardest Modern Broadway Songs to Sing
VOICE OVER: Emily Brayton WRITTEN BY: Sammie Purcell
Anyone who masters the hardest modern Broadway songs deserves applause. For this list, we'll be looking at the most difficult tunes Broadway has produced from 1980 until today. Our countdown includes "Cats," "Hamilton," "Into the Woods," and more!

#10: “Confrontation” “Jekyll & Hyde” (1997)

It’s one thing to play one struggling character. It’s a whole ‘nother thing to play two – much less to play them at the same time. Toward the end of “Jekyll & Hyde,” Dr. Jekyll has a final showdown with his alter ego Mr. Hyde for ultimate dominance. For one thing, the song has some incredibly tough notes to hit. What’s more, the actor playing the role – or, ahem, roles – has to switch back and forth between personalities. That involves modulating their body language, vocal style, and everything in between. That’s certainly a tough line to walk.

#9: “Words Fail” “Dear Evan Hansen” (2016)

The lead of “Dear Evan Hansen” has quite the task to tackle. With songs like “Waving Through a Window” and “For Forever,” it’s possible that no modern musical has as many emotional ballads as this one. But the show would be difficult enough with just “Words Fail.” Throughout the musical, Evan lies to the Murphy family about his relationship with their late son, Connor. He finally confronts the truth of what he’s done through this song – in messy, weepy, fashion. The number is already intricate by design, but the amount of vulnerability and emotion that go into it make it all the more tough.

#8: “Your Fault” “Into the Woods” (1987)

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From the moment that dissonant melody begins, you know you’re in for a treat. “Your Fault” is a Stephen Sondheim sequence on high, with fast-paced lyrics and intricate rhythms. The song takes place in the second act, with all the characters blaming each other for various wrongdoings and mistakes in the most chaotic fashion possible. Memorizing the words to this number is already difficult, but then you’ve also got to master the notes, the rhythm, and the speed. Oh, and you have to do it all while other people are reciting their own, very different parts. But it’s amazing to watch when done correctly.

#7: “Memory” “Cats” (1982)

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Salem Orion Memory

When a tune sung by cats is this touching, you know it’s special. But “Memory” isn’t just the best song from Andrew Lloyd Webber’s famous feline extravaganza – it’s also the hardest. The honor of singing it goes mainly to the person playing Grizabella, a “glamour cat” who’s going through a rough patch and longs for acceptance. The song is inspired by the musical stylings of opera composer Giacomo Puccini, so it features grandiose swells of music filled with emotion. The passion, mixed with the high notes, make this a complex powerhouse number. While it’s a challenging piece, the strength of “Memory” is impossible to ignore.

#6: “I’m Here” “The Color Purple” (2005)

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Top 10 Hardest Songs to Sing

Love songs are a dime a dozen in the musical canon, but self-love shouldn’t be forgotten. Near the end of “The Color Purple,” Celie sings “I’m Here,” a glorious 11 o’clock number filled with confidence and strength. But belting out this beautiful song isn’t as easy as it looks. It builds from a place of quiet contemplation to exuberant passion, rising up to the singer’s higher range and ending with a long stretch of belting. By that last note, the performer has got to be able to pour their entire soul into it, letting out all the love in their heart.

#5: “Satisfied” “Hamilton” (2015)

Lin-Manuel Miranda’s hit musical “Hamilton” is filled with songs that any singer or actor would kill to be able to perform. But not all singers and actors have what it takes. We could’ve gone with the impossibly fast cadence of “Guns and Ships” or the slow build of “Burn,” but nothing is more impressive than “Satisfied.” Angelica Schuyler’s show-stopping number is an intricate blend of belting, and speedy rapping. The performer must nail each unique part while playing the emotion of the song perfectly. Renée Elise Goldsberry gave a perfect performance in the original Broadway production, showing us what a master at work looks like.

#4: “Bring Him Home” “Les Misérables” (1987)

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If there’s one musical that’s a who’s who of famous, beautiful ballads, it’s “Les Misérables.” But they’re also extremely difficult to perform well. “I Dreamed a Dream” is filled with equal parts pain and hope, and “Stars” gives us a full glimpse into one man’s philosophy. But nothing sets us off quite like “Bring Him Home.” The song requires impeccable control from the moment it starts, with its strong, sustained notes and quiet passion that grows into an agonized plea. If you don’t immediately hit those starting notes with precision, you’ve got no shot with the rest of it. If that’s not pressure, we don’t know what is.

#3: “And I Am Telling You I'm Not Going” “Dreamgirls” (1981)

“Dreamgirls” is a singer’s dream, filled with amazing songs that give ample opportunities to show off their range. “Listen” is assuredly a standout number that’s not for beginners. But “And I Am Telling You I’m Not Going” is so difficult that very few performers can pull it off. Jennifer Holliday brought Effie to life on Broadway. And the skill with which she performed this song set the standard so impossibly high that we still talk about her stupendous work today. In the musical, she sings the song in an impassioned plea to her beau Curtis, and explodes with emotion, amazing riffs, and a belt that’s to die for.

#2: “The Phantom of the Opera” “The Phantom of the Opera” (1988)

With an iconic organ opening like that, how could you not think of this number fondly? The titular song from “The Phantom of the Opera” begins as sort of a standard duet between Christine and the Phantom, but ends in a strikingly eerie, beautiful fashion. At the end of the song, the Phantom orders Christine to sing. The performer must then hit a sequence of impossibly high notes, rising in tone, until she finally ends on an E6, which is no simple feat. By the time that final note bursts out, it’s impossible not to be flabbergasted by the technical feat you’ve just witnessed. Before we unveil our top pick, here are a few honorable mentions. “El Tango de Roxanne,” “Moulin Rouge!” (2019) This Moving & Technically Complex Song Sure Makes Our Hearts Cry “So Much Better,” “Legally Blonde” (2007) Each Fast-Paced Lyric Sounds So Much Better Than the Last “Finishing the Hat,” “Sunday in the Park with George” (1984) It’s Not Easy to Sing with This Level of Emotion “She Used to Be Mine,” “Waitress” (2016) She’s Messy, She’s Kind, & She Can Blow You Away with Her Strong & Moving Belts “I’ll Cover You (Reprise),” “Rent” (1996) The Sadness Alone Makes This One Brutal to Perform

#1: “Defying Gravity” “Wicked” (2003)

Kids, don’t try this one at home. With Kristin Chenoweth and Idina Menzel at the center of the original Broadway cast, “Wicked” was bound to feature incredibly difficult songs. After all, they can handle it. But not everyone can! “No Good Deed,” Elphaba’s impassioned wicked witch number, requires tremendous power. Still, nothing compares to the level of skill it takes to pull off “Defying Gravity.” It’s Elphaba’s moment, and it’s one of the most impressive feats of belting on a Broadway stage to date. That infamous high note required for the final riff could intimidate even the most talented vocalist, and it’ll never not be iconic.

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