Top 50 Hardest Songs to Sing

“Wicked” is one of the most famous musicals of the 21st century, and for good reason. It has a litany of unforgettable numbers. One of the most beloved and complicated songs, of course, is “Defying Gravity”, which Elphaba sings (joined in spots by Glinda and the chorus) as she embraces her true power. This arc is evidenced by her dynamics and cadence gradually increasing, eventually culminating in that seemingly insurmountable riff. It’s also the final moment before the end of the first act, meaning it requires some serious acting ability to pull off. Countless people have taken on the piece, but it’s a challenge for anyone to execute well. While some have done it justice, Kristin Chenoweth and Idina Menzel’s rendition remains the blueprint.

Aretha Franklin’s voice was one in a million, which is why it’s so hard to perfectly nail one of her tracks. One of her most complex by far is “(You Me Me Feel Like) A Natural Woman”, a ballad expressing how a lover makes the narrator feel down to her core. Franklin effortlessly shows off her vocal range throughout, ranging from rich lower tones to gorgeous, lilting higher notes. It isn’t a song for the faint of heart, as reaching those without being pitchy is nearly impossible. The self-control needed to pull the technique off while maintaining that passionate, joyful sound is something that only experts have, making this one of the most intricate songs ever.

As soon as those sultry guitars come in, you know you’re in for a performance. Mariah Carey is one of the greatest performers we have, and on the fifth single from her album “Butterfly,” she proved it again. Carey starts off quietly on this sexy, passionate song, content to show off her melisma skills and affords us soft runs all over the place. In the second and third choruses, her voice grows stronger as she lets out those high notes. But, as any good singer should, Carey never loses control, effortlessly switching between her belt and her head voice.

If you think you can throw on a red leather jacket and a bedazzled white glove and this song will be smooth sailing, well then you have another thing coming. Everyone remembers how amazing Jackson was as a dancer and performer, but his vocal abilities are sometimes overlooked. Well, they can’t be overlooked with “Earth Song.” The song speaks to our destruction of our planet and requires real, heartfelt emotions to pull it off. Also, one needs to range into higher notes that aren’t a moonwalk in the park for many singers.

1997 didn’t just give us James Cameron’s masterpiece of a film. It also brought us one of the best songs ever written and performed with it – a song that would be sung at karaoke until the end of time. Still, it might be best to leave this one to the pros! Not only because “My Heart Will Go On” is sung by the incomparable Céline Dion, but also because it’s incredibly difficult to get just right. Dion captures the emotion of the love ballad in a way no one else can with her effortless control. Her voice grows steadily stronger as the music progresses before completely exploding at the end, attacking those high notes perfectly.

Here’s one of the most impossible-to-nail slow jams of all time. Seriously, we don’t know how Lisa Fischer does it. She’s a goddess. It was released in 1991 and remains one of Fischer’s biggest hits to this day. Fischer manages to stretch her notes like no other, and listening to her attain those high notes so flawlessly makes us wish she got more opportunities like this to show off her chops. “How Can I Ease the Pain” requires an incredibly strong belter to get up into that high register while still pouring passion into the words. And once Fischer lets loose on those whistle tones? Please.

It’s not just the high notes that can be difficult to hit. The opening of “Un-Break My Heart” doesn’t necessarily make you feel like the song’s going to be that hard to sing. But then, you hear the incredible range of Toni Braxton. From that first verse, Braxton’s smoky vocals follow through the lower notes of her register with incredible strength and power. On top of that, her talent only shines stronger on the second verse, when she shows us all how low she can go while still maintaining precise control over her stellar runs.

The rock ballad is one of the best subgenres music has given us over the years. And “Total Eclipse of the Heart” is rock ballad execution at its finest. This song not only requires melodramatic, rock ‘n’ roll passion at a high level, but tremendous breath support as well. Bonnie Tyler stays up in that higher register for most of it, and not for nothing, those verses and choruses have a lot of words. With so much movement and not a ton of time to breathe, “Total Eclipse of the Heart” is certainly one of the most impressive ballads of its kind.

20: “Livin' on a Prayer” (1986)
Bon Jovi

Oh, you wanted more whistle tones in modern pop music? Well, Ariana Grande heard you, and she delivered. It’s no secret that Grande is an expert singer, but with her hit “imagine,” she went further than we could have imagined. The song’s chorus requires the singer to make a large vocal leap on the word “imagine,” and necessitates pinpoint precision in its notes. But all that aside, if you want to sound like Grande when you sing this song, you’ve got to try and go for those whistle tones at the end - definitely not an easy task.

“Rolling in the Deep'' was the song that first brought English singer Adele to international stardom, and for good reason. Written in response to a heated breakup she once had, the lyrics tell a personal story: it’s a song about a lover telling her ex that he is too foolish to see how much he could have had with her. It’s an angry, passionate tune: there are no whispers of despair in this brassy number, and only a strong singer with both low- and high-range vocal power can pull it off. Adele beautifully communicates the anger in the track without sacrificing the purity of her sound.

When Jennifer Holliday originated the role of Effie White in “Dreamgirls” on Broadway in 1981, this number brought down the house; Holliday won a Tony Award and was set on the path to pop and R&B fame. This song takes place after a stormy scene where Effie finds out she has been thrown out of her singing group; she adamantly insists to the manager that she is staying, no matter what, because she loves him. Strong, high belting and convincing drama are essential to the musical number, which makes it effective only when sung by a very talented singer and actress. And this isn’t the only difficult song from “Dreamgirls.” “I Am Changing” definitely strains our vocal chords a bit.

Though she performed with Stevie Wonder and Rotary Connection, Minnie Riperton spent most of her career struggling to be noticed–she died tragically young, succumbing to cancer when she was only thirty-one years old. However, she did have one smash hit single, and this is it. “Lovin’ You” is a soothing, repetitive track, seemingly simple, but by no means easy to pull off; some of the notes are so high, they have been mistaken for bird whistles! There actually are some bird twitters in the background, but those sweet fluting notes are all Riperton, who makes them sound amazingly effortless.

We’re not exaggerating when we say “I Believe in a Thing Called Love” is a good time from the first second, with fans fully rejoicing at Justin Hawkins’ amazing vocal range. Indeed, he indulges in all of the eccentricities of glam and hard rock styles. Of course, a good time doesn’t mean an easy one! The entire chorus functions like a minefield that’s hard to travel through without absolute control of your voice. With one high note after the other, Hawkins flies up and down his register without missing a beat. This melodically-sophisticated throwback never ceases to stump even the most capable artists.

Notoriously difficult, “Don’t Rain on My Parade” is from the musical “Funny Girl”, which was based on the life of Fanny Brice. Barbra Streisand, who played the lead role on Broadway in 1964 and won an Oscar for her performance in the movie adaptation, makes it sound quite natural; however, the song’s tricky rhythms, frequent leaps, and consistent high energy have daunted many aspiring vocalists. Although a few professionals like Bea Arthur and Idina Menzel have covered the song, the musical wasn’t revived on Broadway for decades - possibly because of the challenge of finding someone for that dynamic leading role. That changed in 2022, however, with the revival that eventually cast Lea Michele as Fanny.

Inspired by Emily Brontë’s tale of tempestuous romance, the song “Wuthering Heights” focuses on the part of the story where Catherine’s ghost returns to Heathcliff after their many years of anger and misunderstanding in life. The song took the world by storm in 1978, topping charts throughout the UK. Kate Bush has a style that is extremely difficult to imitate, and while her voice sounds natural and sweet in the single’s high falsetto runs, they are extremely difficult for most singers to achieve. And as if that weren’t enough, the backing track gives almost no support–as many karaoke performers have discovered, to their dismay. And, just in case you were thinking about it–no, we wouldn’t try “Running Up That Hill” either.

Every time Steven Tyler looks in the mirror he sees a man with an amazing singing voice. But for most any other vocalist out there who thinks they can sing like Tyler, we have two words for you… “Dream On.” And it isn’t just the vocal range and the sheer power of Tyler’s voice that makes this a tough one. There’s also the change in melody which can catch some singers off- guard. And the same holds true for another difficult Aerosmith track that deserves a mention on this list: “I Don't Want to Miss a Thing.”

“The Bodyguard,” the 1992 movie that stars Whitney Houston as a famous singer and Kevin Costner as her, well, titular bodyguard, is somewhat of a cheesy mess. But that soundtrack is definitely the silver lining. “I Have Nothing” is but one of the amazing singles that came from “The Bodyguard,” and also one of the toughest in Whitney Houston’s roster. The song requires incredible force and resonance, particularly when it hits the chorus. We don’t know about you, but we can’t imagine anyone other than Houston giving this one the passion it deserves.

Originally released in 1955 “Unchained Melody” has been recorded over 1,500 times by more than 670 artists. But for the purposes of this list we will focus our attention on the 1965 version recorded by The Righteous Brothers. We can’t imagine any singer listening to Bobby Hatfield croon and think to themselves that it would be easy to do that. Even Elvis Presley, who has a great voice and does a great version of the song, doesn’t try to hit the same high notes and pull off the same crescendos that Hatfield does so effortlessly.

It seems too far out of reach to picture a time when Mariah Carey wasn’t popping off in her whistle register. Turns out, this time was actually before 1990. The release of “Vision of Love” was actually the first time audiences would hear Carey hit those tones. And it was incredible. Still, the whistle notes are not the only thing that makes “Visions of Love” so impressive. It requires a singer with an incredible depth of range, downright insane breath control, and the ability to transition vocally without a hitch.

While this song is also technically from “Dreamgirls”, it did not appear in the original musical; it was specially written for the 2006 movie adaptation. “Listen” is sung by a character who has felt stifled and uncertain throughout, until she finally breaks out into this show-stopping number and demands that people listen to what she has to say. It is a fierce and dynamic tour de force, with big leaps, florid riffs, and long runs that require a strong, powerful voice to perform well; Beyoncé does an amazing job of keeping up the passion and volume without sacrificing any of that gorgeous flexibility.

Sia has made a successful career writing songs for other singers, and originally, she intended “Chandelier” to be sung by Rihanna, with some sources also adding Beyoncé. But as she crafted the track, she realized it was one she needed to sing herself. Although it is somewhat gritty and raw, describing the effects of hard partying and addiction, “Chandelier” still requires an accomplished singer; from low, rapid mutters, to high leaps and strong held notes, it’s a wild ride. Sia’s voice blends pain and lyricism in a way that makes this song uniquely hers–and because of both her talents and her personal connection with the song, it’s doubtful whether anyone else could perform it so effectively.

Where do we start with this one? “Bohemian Rhapsody” is a prog rock classic. Part ballad, part opera, part hard rock anthem all wrapped up in an almost six minute vocal trip that has humbled many a singer who has taken the ride. And we aren’t the only ones who think Freddie Mercury’s performance of the song is a vocal feat not to be taken lightly. In a Rolling Stone readers poll, Mercury’s performance of the song was voted the greatest in the history of rock and roll. But ya, you can go ahead and try to sing it if you want. Just remember, this is the real life. This isn’t just fantasy.

Christina Aguilera is one of the most prolific singers in Hollywood. Unfortunately, one of her greatest, most difficult songs to sing, is not one of her most famous. “Hurt” is a number from Aguilera’s 2006 album “Back to Basics.” It sort of got buried under the pizazz of the rest of the tracklist, which includes the likes of “Ain’t No Other Man” and “Candyman.” However, in “Hurt,” Aguilera slows things down and delivers a masterful performance with incredible range. The chorus necessitates a kind of emotion and resonance that is rare to come by.

Céline Dion has won acclaim for many dramatic and challenging songs, but this one stretched even her impressive powers: a quiet, introspective beginning leads to a swelling key change, and finally, a passionate outpouring of sorrow that demands strong, sustained high notes relentlessly. As with all deeply emotional pieces, the singer must be expressive without losing the beauty of the sound; not an easy task at any time, but particularly hard when you are belting very high and very loud in front of a large audience. “All by Myself” has become one of Dion’s most iconic songs - despite being a cover of an Eric Carmen original - and there’s a good reason you rarely hear someone else attempt it.

It’s time to talk about key changes! Beyoncé’s 2011 hit “Love On Top” is one of the pop diva’s most fun songs. From the outset, it doesn’t seem like it will be particularly difficult to sing. Not more difficult than any other Beyoncé song, anyway. But, by the end, we’ve found ourselves with so many key changes, we don’t even know how to begin counting them off. As Beyoncé’s voice keeps getting higher and higher, our jaws keep dropping lower to the ground. It’s insanely impressive how high up she can get, never mind the absolute clarity with which she does!

Whitney Houston had a voice unlike anyone else’s. She won fame singing not just original songs, but covers, and classics that had been done a hundred times, like “The Star-Spangled Banner.” However, this tune–originally written and recorded by Dolly Parton–is probably Houston’s most famous. The stamina and versatility required to sing “I Will Always Love You” are just the beginning. Because of the single’s wide range of notes and dynamics, the singer must be able to adopt many different vocal characters, from sweetly quiet to powerfully low and finally to triumphantly (but gorgeously) high. Or, at least, that is the way Houston sang it–and nearly everyone else has been too daunted to tackle it since!

Many of our audience members probably guessed that a vocal performance by Mariah Carey was coming, they just didn’t know which. Like Whitney Houston, Carey seems to be capable of performing vocal feats that are beyond those of regular mortals, and this one is a perfect example. “Emotions” is an upbeat R&B, post-disco hit with no room for rest–one cannot help but wonder at Carey’s constant high-energy belting, seemingly effortless runs, and of course, those incredible high notes soaring up into the stratosphere. A good operatic soprano could probably hit them, but rarely are notes so high heard with such pure and beautiful clarity. It all adds up to make this a fitting choice for our top most difficult song.

Which song do you think would be the hardest to tackle? Let us know in the comments below!