Ahhh, which Broadway songs are the most difficult to sing? That is a topic that will be hotly debated for centuries to come. But here is a list of ten serious contenders based on various sources on the internet. The vocal gymnastics and intensity of emotion to fully realize the scene demands that only the best of the best need apply. Belting out songs night-after-night before live audiences also leaves singers at serious risk of damaging their instruments. This can lead to cracks, warbles, and raspiness. So unsustainable vocal habits are out of the question. With that in mind, here are some incredibly difficult songs to pull off.
“Roses Turn” Gypsy
This song brilliantly captures the unhinged state of mind of Mama Rose [based on the real person Rose Hovick] who pushed her daughters into show business in an attempt to heal her own past wounds. Sometimes it’s the high notes or the fast pace of a musical piece that makes it so challenging to pull off. Other times, as in this case, it’s the intensity of emotion, to the point of being frightening, coupled with the ability to tell the story—and tell it well—that is a huge feat.
“Gethsemane (I Only Want to Say)” Jesus Christ Superstar
In the Andrew Lloyd Webber and Tim Rice rock opera, the tenor singing “Gethsemane” needs to express the intensity of the internal struggle of Jesus before being put to death while also being able to hit unforgettable high notes while crying out with great anguish. Many have tried, but few have succeeded in the challenge.
“Rainbow High” Evita
Even though the song is relatively short, Evita’s “Rainbow High” requires a hearty spirit from beginning to end to capture the sheer determination of the First Lady of Argentina Eva Peron. The singer must belt out lyrics with several key changes—which truly takes some star qual-it-y!
“Bring Him Home” Les Misérables
This heavenly, measured, but powerful song requires tremendous control and plenty of high notes. Partially sung in falsetto, Alfie Boe characterizes what makes Jean Valjean’s earnest prayer so breathtaking. To make things more challenging, the song is sometimes sung while sitting down. Tenderness of voice is a must!
“Guns and Ships” Hamilton
Among the masterful syllables-per-second contenders is Hamilton’s French ally Lafayette. Like a cheetah, the Frenchman’s rap is quick and sweet. However, it punctuates the musical with such impact and charisma, it’s no wonder Lafayette is so many people’s favorite Hamilton character. Not to mention, Lafayette actor Daveed Diggs performs this challenging rap while taking an impressive leap—all without skipping a beat!
“(Not) Getting Married Today” Company
This extremely fast-paced Sondheim song is a comical take of a pre-wedding panic attack. Besides managing a megamouth full of words and finding places to breathe, the singer must make sure to articulate clearly enough so the audience can understand all of the packed-in jokes. It requires a masterful comical actress like Madeline Kahn to pull it off.
“Defying Gravity” Wicked
In a moment of personal empowerment finishing the first act, the fiery Elphaba flies on her broom all the while belting out emotional high notes. She is required to be hoisted into the air on a harness and have several microphone packs in her witchy hat, singing her heart out and hitting a top F. It’s no surprise that casting selected the top-notch vocal talent Idina Menzel in the original Broadway.
“The Phantom of the Opera” The Phantom of the Opera
As Christine follows the Phantom of the Opera into his gothic lair, her high notes just seem to get higher and higher, ending in an outrageous E6—much along the lines of Mariah Carey’s astounding vocal capabilities.
“And I Am Telling You I’m Not Going” Dreamgirls
In the 2006 film Dreamgirls, Jennifer Hudson nailed her performance of this extremely challenging marathon of a song. Digging deep into the complex emotions of the character Effie White, Hudson, and other actresses who’ve played the role—especially the jaw-dropping talent Jennifer Holliday—must simultaneously tackle the nimble riffs while emoting with power and force in this desperately passionate masterpiece.
”Glitter and Be Gay” Candide
When it comes to challenging Broadway songs, the Leonard Bernstein operetta Candide probably sets the record for most difficult. For six minutes, the soprano’s florid vocal performance ranges from a flowing legato to trills as high as Eb6. The singer has moments where she reclines on a couch, making it all the more difficult to breathe sufficiently. Glitter and Be Gay requires highly intricate work between the singer, conductor, and orchestra. Not to mention, this level of expertise must be combined with a large scoop of comedy!
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