Top 10 Hardest Classic Broadway Songs to Sing

“Here she is, boys!” And, if you ever get the opportunity to sing this song, you better be ready to work. Throughout “Gypsy,” Rose works as hard as she can to make her daughters famous, striving to get them onstage and make them perfect. By the time “Rose’s Turn” comes around at the end of the second act, she has shed all pretense that anything she’s done is for her daughters, admitting to wanting to live out her dreams through their successes. Not only is the song incredibly difficult to sing, but it takes a strong and capable actress to perform the complexities and nuances of Rose’s character while still delivering a big, bombastic, show-stopping number.

When a song becomes a popular tongue twister, that’s pretty iron-clad proof it’s a difficult song to perform. Originally sung in Gilbert and Sullivan’s “The Pirates of Penzance,” this famous tune pokes fun at the so-called “modern education” received by the 19th British Army, and continues to be parodied and referenced more than 100 years later. While it may be one of the most well-known songs on our list, don’t be fooled – not just anyone can pull this song off. The number’s breakneck pace requires the performer to have excellent diction and rhythm, making it one of the hardest songs to sing from the classic era.

You might not immediately think of “The Sound of Music” when you hear the word “hardest,” but you’d be surprised how many difficult songs have snuck their way into this beloved musical. We could have gone with the soaring heights of “Climb Ev’ry Mountain,” or the swelling emotion of the musical’s titular number, or the yodeling in “The Lonely Goatherd,” but we couldn’t ignore the rousing energy of “Do-Re-Mi.” The words may be simple, but the number of progressions and arrangements contained within this one song are anything but. Add in that amazing high note at the end – thank you, Julie Andrews – and you’ve got yourself a winner.

When it comes to word memorization, it doesn’t get much harder than “(Ya Got) Trouble” – well, maybe a bit harder, but we’ll get to that later. “The Music Man” has a few songs that involve complicated rhythms and more words than we can count, but this song takes the cake for the most difficult. “(Ya Got) Trouble” takes place early on in the show, when conman Harold Hill convinces the parents of River City that pool tables are sure to rot their children to the core. The actor playing Hill has a lot of ground to cover in little time, throwing out lyrics nonstop while walking a fine line of believability and smarm.

When it comes to writing a romantic duet, Rodgers and Hammerstein tend to go all out – and, while we love the gorgeous, choral tones of “You’ll Never Walk Alone,” the award for the toughest song in “Carousel” has to go to “If I Loved You.” In the show, the song is sung between Billy and Julie as they hesitantly start to explore their feelings for each other. The song offers each performer a moment to shine, with its soaring, impressive notes, but the real challenge – as usual – is in the acting. Both Julie and Billy have to portray romantic interest, but walk on eggshells at the same time, making for an intricate dance between what they’re saying and what they mean.

When you put Leonard Bernstein and Stephen Sondheim together, you’re bound to get some of the most difficult songs in the musical theater canon. “West Side Story” is filled with great examples of its composer’s and writer’s prowess – Tony’s introductory number “Something’s Coming,” in particular, comes to mind – but we decided to go with a much more comprehensive production. “Tonight” involves nearly every character in the show singing at once, meaning all of those singers have to find the balance, harmony, cadence, and rhythm to make the song flawless. It’s a difficult task – we’re not sure if either movie adaptation really got it just right – but the original Broadway cast does it to perfection.

If we had to guess which musical has the most opportunities for wild moments of belting, we might guess “Jesus Christ Superstar.” There’s, of course, Judas’ rocking number “Heaven on Their Minds,” but it’s just impossible to deny the power of “Gethsemane (I Only Want to Say).” In the song, Jesus pleads with God to tell him why he has to die, unleashing a swell of anger and sadness. The song builds, each note getting higher and higher, until Jesus lets out a breathtaking, rock ‘n’ roll scream, one that has us feeling all of his frustration and fear in a single note. It’s an amazing moment, and a really difficult one to nail.

When you watch Barbra Streisand perform in the original Broadway production, she makes it look easy. So easy, in fact, that we sometimes forget just how difficult it is to do what she’s doing. So is the case for many songs in “Funny Girl.” Babs is amazing in the role, pulling off songs like “People” with astounding range and diction. But no song proves her stardom more than “Don’t Rain on My Parade.” The song takes place when Fanny Brice decides to take a chance on love, and requires the performer to not only hit and sustain incredibly high notes, but to do it with such exuberance that we can’t help but be on her side.

We bet you thought we were done with the tongue twisters! Impossible, because this list would not be complete without “Getting Married Today” from the 1970 musical “Company.” Now, you might listen to this Stephen Sondheim classic and think it’s just about getting all those words right, right? Wrong! “Getting Married Today” – a song with a verse that requires the performer to sing 68 words in about 11 seconds – needs so much more than memorization. The performer has to have perfect diction, pitch, breath support, and comedic chops to knock this number out of the park. Lose just one of those things, and you’ve lost the audience.

Before we unveil our top pick, here are a few honorable mentions.

“Anything Goes,” “Anything Goes” (1934)
Singing This Song Is Hard Enough Without Tapping It Too

“Summertime,” “Porgy and Bess” (1935)
The Livin’ Might Be Easy, but This Song Sure Isn’t

“The Impossible Dream,” “Man of La Mancha” (1965)
More Like the Impossible Song!

“Big Spender,” “Sweet Charity” (1966)
This Performer Better Have Some Big Pockets & Even Bigger Pipes!

“Green Finch and Linnet Bird,” “Sweeney Todd: The Demon Barber of Fleet Street” (1979)
It’s Right There in the Song: “How Is It You Sing?”

If you’re a soprano and you’re looking to impress, this one is a good number to add to your repertoire. But, be warned – make sure you can nail it. “Glitter and Be Gay” comes from Leonard Bernstein’s “Candide,” and is one of the most difficult songs a performer can sing for a few reasons. For one, they have to hit a number of wild high notes, including not one, not two, but three high E-flats. In addition to having impeccable control and virtuosic talent, the performer also has to be incredibly funny, hitting their marks and jokes with expert comedic timing.