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10 Songs From Musicals That Are Unexpectedly Difficult To Sing, According To Reddit

2021 brought musical theater lovers adaptations of Dear Evan Hansen, In The Heights, Tick, Tick… BOOM!, and even more. While 2022 has been considerably quieter, information drops about Matilda and the long-awaited Wicked musical have kept fans on the edge of their seats. While the songs and stories of musicals are widely known, the shows themselves are largely inaccessible thanks to distance, cost, or pandemic guidelines.


Because of that, many fans are left to enjoy musicals on their own, downloading the soundtracks, singing along, and imagining everything in between. There’s a different level of emotional connection that comes from fans singing the songs themselves, but that can be hampered by songs that are surprisingly difficult to sing. Some songs are widely known for being impossible for anyone without extensive training, but musical theater fans took to Reddit to discuss the secret ones they weren’t expecting to struggle with as much as they did.

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10 “A New Argentina” — Evita

The musical Evita follows the life of Eva Perón as she made her way from poverty to power, investigating how she became an icon in Argentina. The first act ends with the song “A New Argentina,” in which Eva and Juan Domingo Perón gain social and political power through the promises they make to the people.

The song is deceptively simple, with Eva’s short phrases seeming more like dialogue than a song – until you try to sing it. As bethholler said, “Very few performers can sing it without sounding like they are screaming.” This is consistent with how Patti Lupone talks about the musical: “I was screaming my way through a part that could only have been written by a man who hates women” (via The New York Times).

9 “Giants In The Sky” — Into The Woods

Despite being played by the incredibly talented Daniel Huttlestone in the movie, the role of Jack in Into the Woods is generally played by a man in his late teens or early 20s, and his songs are written for someone who’s spent all that time training. “Giants in the Sky” is a wonderful song, but it’s also extremely difficult.

Redditor psychotwilight calls it a song “written by a sadist,” going on to define its complexity as: “Hard notes to hit, quickly jumping from high notes to low notes, complicated lyrics that are tricky to memorize and enunciate, the meter changes quickly, requires a really good actor with powerful stage presence to sell it well.” It’s a powerful song, but definitely not one that beginners can tackle without some serious effort.

8 “Wishing You Were Somehow Here Again” — Phantom Of The Opera

Christine’s songs in The Phantom of the Opera are famously difficult, but most people focus on her most show-stopping, high-pitched numbers. However, according to Redditor im_not_bovvered, Christine’s song to her father is actually “one of the hardest musical theater soprano songs out there.”

When performed well, the song feels remarkably calm, but it takes a talented singer to keep that emotional tone while also hitting the right notes. Petite_Courtney explains the song’s complexity: “A lot of people focus on the high E, but what really makes her songs hard is a lot of the lower pitches. Any Christine actress needs a huge range, but also one that’s very comfortable in her breaks.”

7 “I’m Alive” — Next To Normal

Next to Normal came out on Broadway in 2008 to much fanfare, but it remained relatively unknown to the public until it was featured in one of Riverdale‘s infamous musical episodes. The musical follows one woman’s attempt to manage her bipolar disorder while also grieving the loss of her son.

One of the show’s most popular songs is “I’m Alive,” sung from the perspective of her son (or her disorder, depending on the interpretation). While the song has few difficult notes, Redditor Sarcherre describes it as “a simultaneous marathon and sprint.” It’s hard to have the breath control to survive the song and, as Carnivile explains, “It’s also really boring if you don’t have a good performer. You need a very energetic voice because otherwise it’s just repeating I’m alive 60 times.”

6 “By The Sea” — Sweeney Todd

Musical theater fans are likely to be rewatching Halloween classic Sweeney Todd in the next couple of months, but they may find it surprisingly difficult to keep up with Helena Bonham Carter as she attempts to seduce Johnny Depp’s maniacal barber into running away with her.

“By the Sea” isn’t very difficult when it comes to the notes that Ms. Lovett sings, but XenoVX explains that the complexity comes in the phrasing: “[Sondheim] mostly isn’t that bad in terms of range but is very challenging to just get the lyrics correct while maintaining proper phrasing and acting with the intention of the lyrics.” There’s a lot to say in very little time, and it takes a lot of skill to sing it clearly and convincingly.

5 “Endgame #3” — Chess

Many musicals are based on historical events, with Chess using a literal chess tournament as a metaphor for the Cold War. On his podcast Get Onto My Cloud, Tim Rice spoke about the musical in January 2022, stating that the success of Queen’s Gambit has made it so the show may soon get a Broadway revival and/or a movie.

The song “Endgame #3” takes place at the climax of the musical, when both the chess tournament and the personal crises of the characters are on the line. The instrumental is extravagant, which could trick audiences into assuming singing it is simple. But as pickseese says, “In every live recording I’ve heard, most of the cast (even pros) are fully out of breath or struggling by 3/4 of the way through.” This musical is not for the faint of heart.

Rodgers and Hammerstein’s musical Carousel follows the love story of Julie Jordan and Billy Bigelow as they go through life’s complications. Before things fall apart, they sing “If I Loved You,” a song that teases their attraction without outright saying it.

Though the song is relatively simple when it comes to the singers’ range, nearly every word is extended. As 16note put it, “You need breath for days to make it through that song’s phrases, and that’s even before you get into the acting challenge of the scene.” There are some amazing duets out there, but this one can be incredibly difficult to pull off unless both parties happen to be practiced performers.

3 “Maria” — West Side Story

The classic musical West Side Story was just redone in 2021, bringing its soundtrack back into popularity. For all its complexities, though, its hardest song might be masquerading as its easiest: “Maria.”

Redditor IrmeliPoika explains the surprising choice: “It has a pretty difficult melody, the rhythm is kinda deceptive and there are some pretty impressive high notes. The lyrics mostly being ‘Maria’ also kind of make it harder, because you can’t rely on words to get the emotion through.” Repetitive songs often seem easiest, but they can be very difficult to do right.

2 “Send In The Clowns” — A Little Night Music

A Little Night Music explores a tangled mess of mismatched couples who gradually find their way into better relationships. In the midst of the many affairs is Desiree, an actress who struggles to find contentment in life’s offerings.

“Send in the Clowns” is an incredibly popular song from this musical, yet it hides its complexity in plain sight. While the audience focuses on the lyrics and notes, the timing is toying with them. As Shh04 explains, “it starts at 12/8 time and before you finish a phrase, goes to 9/8, and alternates between the two throughout the song.” Success means the audience never notices how difficult it is.

1 “Shiksa Goddess” — The Last Five Years

The Last Five Years follows Jamie and Cathy as they attempt to make their relationship work, with one looking back on the relationship from its ending and the other seeing it progress from beginning to end. While the musical is known in the theatre community for being extremely complex, it didn’t seem that hard in the 2014 movie adaptation, especially Jamie’s songs like “Shiksa Goddess.”

However, as Ethra2k points out, “Jason Robert Baritones are basically tenor ranges but with a full baritone sound.” Because his songs don’t stay within a clear vocal range, they can be surprisingly difficult to manage.

NEXT: 10 Non-Musical Movies That Have Been Made Into Stage Musicals

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