Top 20 Hardest Modern Broadway Songs to Sing

The duet is a Broadway standard. In a lot of productions, it is usually performed by a male and female actor. But this one comes from two stellar ladies. “Sonya & Natasha” is sung by its two titular women, and comes after the latter breaks off her engagement with Andrey in order to pursue Anatole. Sonya, worried about her cousin, begs her to reconsider and the two begin to argue. The music perfectly matches each woman’s varying emotions at any given moment, giving them a chance to give and take, while working off each other’s vocals. Both women have a moment to show off their chops, and absolutely nail every note in this immaculate duet.

Stephen Sondheim is famous for writing some of the most difficult songs in the musical theater canon. In “Sunday in the Park with George,” he delivers some of his best work yet. “Putting It Together” is a particularly tasking Act 2 banger, but we can’t imagine the power it takes to sing “Finishing the Hat.” In Act 1, the main character George belts this tune about his relationship with art, women, and everything under the sun. Sondheim’s orchestrations build the song up to a stunning climax that’s filled with emotion about complex ideas that would be difficult for just any actor to convey. Add in the fact that the tune’s structure itself is pretty complicated, and you’ve got a monster of a number.

You’ve heard about duets, trios, or even quartets. But a true blue octet is pretty hard to come by. In Adam Guettel’s “The Light in the Piazza,” Fabrizio and Clara are two young people in love. For the song “Octet,” the strength of their passion affects everyone around them. Emotions throughout the tune run the gamut of the spectrum, but the hardest thing about this number is staying together. With so many intricate moving parts, it’s important the singers stay on top of their game, not allowing even the slightest of slips. When all that hard work pays off, the song comes together beautifully. But it sure is easy to get wrong.

With range like this, who needs to be able to spell? “The 25th Annual Putnam County Spelling Bee” is known for its lighthearted and silly numbers. But one tune stands out from the rest, both because of its serious subject matter and its difficulty. “The I Love You Song” is a trio between spelling bee contestant Olive, her mother, and her father. The parts meld together beautifully, but the range (particularly the upper register) for every character is remarkable. One notable moment comes when the singer who plays Olive has to hit a very high note, infused with terror and sadness in equal measure. This song is pretty daunting, so hearing it executed with such mastery is nothing short of amazing.

There are a couple of songs that a singer can choose that immediately let you know how good they are. From the opening notes of “I Dreamed a Dream,” you better hope that you’re in good hands. Because if not, things could go terribly wrong. The song is a lament sung by Fantine just after she’s been fired from her factory job. It’s the only solo number performed by the character and the first real glance we get into her mind. There’s a lot riding on the song emotionally, and judging by the complexity of its structure, it can be quite difficult to reach those emotional heights. When a good performer gets a hold of this tune, however, there’s absolutely nothing like it.

“Hadestown” is an amazing musical filled with intricate and exciting modern music. The show follows the story of Eurydice and Orpheus, and requires both actors to be tremendous singers. In particular, the song “Flowers,” sung by Eurydice, can be an amazing feat of vocal achievement. Eurydice belts the tune after she arrives in Hadestown while she slowly loses her memory of the world above. This number has great range on both ends of the spectrum, but the performance is what pushes it over the edge. The actress playing Eurydice has to act through the feelings of a woman losing her way and mind, while still delivering a hauntingly beautiful melody.

If you’ve never heard of “Ride the Cyclone,” we suggest you check it out right now. The experimental show follows a group of teenagers who die on a rollercoaster and then compete for a chance to come back to life. “The Ballad of Jane Doe” is sung by the eponymous headless girl, whose identity is a mystery since no one claimed her body after the accident. The technical demands of this tune are out of this world. It requires a true soprano to hit its high, chilling notes, while flying at the same time. As if that’s not enough, the performer has to quickly adapt when the song later changes to a jazzier sound. Truly a rollercoaster of a musical number.

An Act 1 closer is an essential part of any musical. You want to end on a strong emotional note that leaves the audience excited to come back for more. “Legally Blonde” does exactly that with the notoriously difficult “So Much Better.” Elle Woods sings this song just after finding out she’s won an internship that no one thought she would get. It’s a moment of pride and exaltation for the character, and the vocals and choreography certainly won’t let you forget it. The actress playing Elle sings the high notes pretty much all the way through while still having to dance. Seriously, the stamina needed to move like this while belting out those notes must be astronomical.

There are many tasking songs throughout the acclaimed musical “Hamilton.” Some of them are notable for their particularly difficult rap flow, while others require singing chops that only a few can boast of. Among the latter is the heartwrenching Act 2 song “Burn.” The number is performed by Eliza Hamilton after she learns of Alexander’s affair and burns all of his letters to her. Emotions run high throughout the tune, as Eliza grapples with her anger and sadness. Due to all of these feelings being conveyed at the same time, the song can be quite difficult to maintain, pitch-wise. It demands complete control from the singer, especially in the verses, and “Hamilton’s” Phillipa Soo absolutely nails it.

It’s hard enough finding one singer who can nail the dramatics it takes to be a queen. Try finding six! “Six” is a musical that requires actors, singers and dancers of the highest quality. Out of all the songs, however, “All You Wanna Do” is one of the most difficult to perform. Sung by the actor playing Katherine Howard, the sexy, high-energy number finds the character grappling with her predatory relationship with the King, and coming to a strong realization by the end. Hence, the emotional arc is pretty difficult to convey, and when you add in the range required, you’ll realize you’d have to do all you gotta do to execute it perfectly.

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.

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.

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.

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.

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.

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.

“Dreamgirls” is a singer’s dream, filled with amazing songs that give ample opportunities to show off their range. “Listen” and “I Am Changing” surely are standout numbers that are 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.

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. “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.

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.

“I’ll Cover You (Reprise),” “Rent”
The Sadness Alone Makes This One Brutal to Perform

“El Tango de Roxanne,”Moulin Rouge!”
This Moving & Technically Complex Song Sure Makes Our Hearts Cry

“She Used to Be Mine,” “Waitress”
She’s Messy, She’s Kind, & She Can Blow You Away with Her Strong & Moving Belts

“Pity the Child,” “Chess”
We Pity the Singer Tasked With This One

“I’m Breaking Down,” “Falsettos”
We’re Breaking Down Thinking About the Prospect of Having to Sing This

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,” 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.