Top 20 Hardest Broadway Songs to Sing

What’s the one thing every musical needs? An inspirational tune to get you through the hard times – and for extra points, make it incredibly difficult to sing. In Rodgers and Hammerstein’s “The Sound of Music,” Maria – who is training to be a nun – falls in love with Captain von Trapp, the father of the children she serves as a governess for. Afraid of her feelings, she seeks advice from the Mother Abbess. The Mother Abbess sings “Climb Ev’ry Mountain,” a first act closer filled with numerous successive, high sustained notes that can’t be easy to sing beautifully – so it makes sense that the song is usually sung by a classically trained soprano. It’s an inspiration to Maria, but also immensely impressive.

#19: “She Used to Be Mine” “Waitress”

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This one is full of high highs and low lows – talk about the importance of range! In the “Waitress” musical based on the 2007 film of the same name, the main character Jenna sings this song as a meditation on the ways her life has gone wrong, and how she’s lost herself in the process. Not only is that a lot of emotional range to cover, but also the actual vocal range of the song is no easy feat. Sara Bareilles – who wrote the music and lyrics for the show – sings a version of this song herself, with a vocal range stretching from F3 to D5. Take that already difficult span and add in the emotional weight of performing on Broadway, and you’ve got yourself a difficult song to perform.

#18: “Made of Stone” “The Hunchback of Notre Dame”

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Everyone knows it can be hard to hit the high notes, but have you ever tried it while maintaining the physicality demanded to convincingly portray the bellringer? Probably not. Quasimodo, the titular Hunchback of Notre Dame, sings this killer song that contemplates the impending fate of his lost love, Esmeralda. The song requires the actor to be completely raw in their emotions – which is something that actors should expect and be able to do. However, sometimes, the actor playing Quasimodo also has to affect a certain, hunched physicality that makes it all the harder to really nail those high notes – especially in the last chorus.

It takes some serious lungs to pull this one off. In Andrew Lloyd Webber’s musical “Evita,” Eva Peron sings this incredible song as she prepares to tour Europe. It may not be quite as memorable as the show’s other signature songs, such as “Don’t Cry For Me Argentina” or “A New Argentina,” but it’s the most difficult in the show – and it takes a truly great singer to push it over the edge. The range of the number is fairly large: the lead has to sing strange intervals, and the style changes throughout. Add in those key changes, and you’ve got yourself one heck of a song – especially when it’s sung by one of the greats, Patti LuPone.

It can be hard enough to pull off a really difficult solo – it can be even harder to pull off a really good duet with another person. But, have you ever tried to sing a duet with yourself? Well, as you can probably imagine, it’s no easy feat. After Dr. Jekyll’s evil alter ego Mr. Hyde kills his love, Lucy, Jekyll decides to confront Hyde about it… so he confronts himself. And sings a duet… with himself. We’ll forgive you if you’re confused, because it takes a really talented actor to pull off this musical number. The actor is required to switch on a dime, changing their voice, physicality, motives, and everything else. And the actual singing ability required? Pretty hard, too.

#15: “Rose’s Turn” “Gypsy”

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Stephen Sondheim does nothing if not give his actors incredible material to work with – and this stellar eleven o’clock number from “Gypsy” is no exception. Rose sings the song towards the end of Act II when she finally admits she’s been pushing her daughters towards fame to live vicariously through them. It’s not as melodic as other songs in “Gypsy,” but what pushes “Rose’s Turn” over the edge isn’t necessarily the musical quality, but the emotional work that needs to go into the performance. The audience has been wondering about the motivations of this character for the whole show, and here, she finally admits what they are. When done right, it can be terrifying – filled with ambition, sadness, anger – all of it.

When you think of Broadway, you think of big, brassy showtunes. Well, “Chess” definitely isn’t the quintessential Broadway musical, with music written by ABBA’s Björn Ulvaeus and Benny Andersson and lyrics by Ulvaeus and Tim Rice, but that almost makes it harder to pull off. The song starts off slow, just a man singing over a piano, reminiscing about his horrible childhood and how it affected his life. But then, the drums hit – and the song becomes more of a powerful rock anthem, where the notes get higher and higher as the song goes on. It requires a heavy amount of power and range, as well as the ability to pull off the arena rock sound that gives the song its edge.

#13: “So Much Better” “Legally Blonde”

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If you love Broadway, then you love a good belt – and especially a good belty, sustained note at the end of a big number. At the end of Act I in the 2007 musical version of “Legally Blonde,” Elle Woods finds out she landed an internship with Professor Callahan, even though no one expected her to. She breaks out into this rousing song, which includes a heck of a lot of movement, dancing, and running around the stage. This is far from the only number in the show that requires an incredibly in-shape performer – “Whipped Into Shape” is a physical feat in and of itself that we could only dream of attempting – but that final, long, joyous note in “So Much Better” gets us every time.

#12: “Your Fault” “Into the Woods”

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When have you ever known Sondheim to make things easy on his actors? Never, and especially not in “Into the Woods.” There are plenty of extremely difficult, wordy songs to sing – “On the Steps of the Palace” comes to mind – but the pacing challenge that is “Your Fault” is without a doubt the toughest song in the show. The number is fast, and filled with so many words even some of the best singers can’t wrap their mouths around them. Not only that, but it’s also got multiple singers involved – so you’ve got a bunch of other people to worry about. Did we mention it’s fast? And wordy? It’s just really hard. Props to anyone who can pull it off.

#11: “I’m Here” “The Color Purple”

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If the end of Cynthia Erivo’s Tony performance doesn’t give you chills, then what will? “I’m Here” serves as the culmination of Celie’s journey throughout the show, and it’s an emotional powerhouse showcase for the actress lucky enough to play the part. Vocally, the song is all over the place, requiring the actress to use her belt and her mix at varying intervals, before exploding into that final section that, if done correctly, leaves the audience weeping. But in addition to its vocal challenges, it’s all about learning to love yourself first and foremost. It’s part of an actor's job to bring all that emotion to the forefront, but when you’re able to do that while executing those notes perfectly, that’s truly something.

#10: “Major-General’s Song” “The Pirates of Penzance”

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Now widely known by theater kids everywhere as warm up exercise, the tongue twisting, vocal challenges of “Major-General’s Song” cannot be overstated. Probably the most famous of the patter songs written by the duo Gilbert and Sullivan, the song is sung by Major General Stanley as he introduces himself to the other characters and the audience. It’s an extremely comedic, satirical song, which can get lost in the mix if you don’t sing and perform the lyrics perfectly – and with so many words to get through and so much alliteration in the mix, it’s a challenge for any actor worth their salt.

#9: “Memory” “Cats”

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We’re going to focus on another Andrew Lloyd Webber original – but don’t worry, it won’t be the last. “Memory” is without a doubt the most famous song from “Cats” – maybe the most famous song from a musical, period – but also one of the hardest songs to sing in the show. Upon first listen, “Memory” might sound a bit repetitive, but that’s exactly what makes it so difficult – those high, slow, repetitive belty notes can be difficult to sustain. To convey the emotional intensity of the song through those repetitive melodies, the actor has to stay on top of their game. Plus, if an actor can make us care about a disgraced … cat? We think they’re doing a good job.

“Hamilton: An American Musical” is chock full of incredibly tough and rewarding songs for actors. You’ve got Angelica’s amazing showcase in “Satisfied,” and of course the show stopping “The Room Where It Happens.” But for this entry, nothing gets us more hype than “Guns and Ships.” The running gag for Lafayette at the beginning of the show is that he hasn’t quite mastered the English language yet. So by the time “Guns and Ships” rolls around – and Lafayette busts out in one of the fastest verses we’ve ever heard – the audience is rightly amazed at his mastery of words and rhythm. We hope all of the amazing Lafayettes out there have “rapping with a French accent” right at the top of their resume.

#7: “Bring Him Home” “Les Misérables”

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Folks, songs can be deceiving – they might sound slow and repetitive, but those very things can make it incredibly difficult to perform well. So is the case with “Bring Him Home,” a gorgeous song from the 1980s’ musical “Les Miserables.” This may not be the most high energy song in the show, but when the right actor performs it? Boy, does it leave an impact. The song has a steady, measured melody that builds and builds, both vocally and emotionally – it gets pretty high for the male voice, and requires a ton of control. Props to every Valjean who has nailed it live.

#6: “And I Am Telling You I’m Not Going” “Dreamgirls”

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There are some songs that are so difficult, they’re really only meant to be sung by a handful of people – and this is one of them. When Jennifer Holliday originated the role of Effie in “Dreamgirls” on Broadway, she did so to thunderous acclaim – and her most memorable moment from the show came in the form of its first act closer. “And I Am Telling You” is written as a plea to Effie’s lover, Curtis, asking him not to leave her. But the way Holliday sings it, it’s more of a demand. She sings with such power and force, almost every single performance that’s come since – of course, barring the great Jennifer Hudson – feels subpar.

Jesus Christ, please save us from all the terrible renditions of this song! For real, if you’re going to attempt this, you better be a tenor worth your salt. This powerful song comes at about the middle of Act II of “Jesus Christ Superstar,” as Jesus becomes more and more doubtful of the task he must complete … namely, dying. On a pure acting level, it takes a lot of acting chops to humanize the literal lord Jesus, which this song requires the actor to do. But more than that, the notes the actor has to hit are absolutely ridiculous. Seriously, it’s akin to an act of God in and of itself that anyone can hit those babies.

Defying gravity? Try defying expectations with how incredibly difficult this song is. When Elphaba and Glinda go to meet the Wizard, they find out he’s not as nice as they initially believed him to be. “Defying Gravity” serves as the moment Elphaba decides to renounce the Wizard and all his cronies, and it’s an incredibly tough act to land. Elphaba has plenty of big, belty moments in the show – “No Good Deed” is definitely a doozy – but what’s really astounding about this performance are the physical demands behind the song. As originally staged, the actress playing Elphaba has to sing all those ridiculously high notes while literally suspended in mid air. Talk about flying high.

#3: “Getting Married Today” “Company”

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Sondheim is nothing if not known for his words. And 1970’s “Company” has a plethora of tough, wordy songs. We almost went with “Another Hundred People,” but “Getting Married Today” takes the cake. Amy sings this song as an anthem to cold feet everywhere in the moments before her wedding. Through the song, Amy completely self-destructs – becoming more and more anxious, and singing more and more quickly until she comes to the end. Not only is the song extremely fast-paced and wordy, but it’s a tough comedic line to walk. The audience has to be able to laugh at Amy while simultaneously feeling bad for her as they watch her fall apart onstage. But, when it’s done right, it’s hilarious and impressive to boot.

Sing, my angel of music! Sing, for me! And make it as high as humanly possible! This one is a doozy, folks. The titular song in Andrew Lloyd Webber’s “The Phantom of the Opera” comes when Christine first follows the Phantom down into his lair – and the end of the song is absolutely killer. The Phantom begins to magically draw notes out of Christine, each one higher than the last. By the time she finally gets to the end of the tune, she lets out an E6 – the highest note in the song, and in the show. The Phantom gets his own moment to shine later with the very difficult “The Music of the Night,” but an E6? There’s nothing more impressive than that … poor Christine. Before we get to our top pick, here are some honorable mentions. “Dead Girl Walking”, “Heathers: The Musical” If J.D. Doesn’t Kill You, That Final Note Will “Octet”, “The Light in the Piazza” And You Though a Duet Was Hard “Kiss Me”, “Sweeney Todd: The Demon Barber of Fleet Street” A Duet Tougher Than Meat Pies “I Am What I Am”, “La Cage aux Folles” Sometimes Being Yourself Is the Hardest Thing “Raise a Little Hell”, “Bonnie & Clyde” Raising Hell’s Never Been Harder

Dangle a shiny object in front of a soprano and you can bet they’ll try to sing it – but to sound good on “Glitter and Be Gay,” you’ve got to have some serious chops. First of all, the comedic chops needed to really sell this performance are no joke – it’s an extremely physical song, which can be a challenge when you’re consistently hitting high E-flats – three, to be exact. In addition to those ridiculous notes, there are so many long, languid passages that require extreme fluidity and control. If you’ve got the guts to even attempt this one? Well, we salute you. Glitter and be gay, my friend!