Top 30 Most Difficult Songs to Sing

Top-30-Most-Difficult-Songs-to-Sing

Welcome to WatchMojo, and today we're counting down our picks for the Top 30 Most Difficult Songs to Sing.

We won’t be including Rap songs, as that’s a list for another day.

#30: “Un-Break My Heart” (1996)
Toni Braxton
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.

#29: “How Can I Ease the Pain” (1991)
Lisa Fischer
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.

#28: “imagine” (2018)
Ariana Grande
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.

#27: “Don’t Rain on My Parade” (1964)
Barbra Streisand
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.

#26: “Go the Distance” (1997)
Michael Bolton

It’s widely recognized as one of Disney’s most motivational songs. Paradoxically, you may need to listen to the track just to make yourself believe that you can actually sing it. The notes soar higher than Olympus itself, and the lyrical context requires the performer to belt each one with unwavering vocal confidence. It was originally tackled by Roger Bart for the “Hercules” soundtrack, followed by Michael Bolton, Ricky Martin, and an assortment of Walt Disney World cast members. You’d better have a brave choral range to conquer it, as well as the ability to convey a challenging scope of emotions. If you can convincingly nail both the vulnerability of its opening and the epic crescendo of its finale, then you just might please the gods!

#25:“You Raise Me Up” (2003)
Josh Groban
“You Raise Me Up” was originally written by the duo Secret Garden. The Norwegian-Irish twosome released the track back in 2002 and since then it’s gone on to be covered by over 100 different artists both male and female. One of the most popular covers is the 2003 version by Josh Groban and copying that version is quite difficult for other male singers. Groban’s vocal range is wide and trying to replicate it isn’t easy, or even possible, for many other male vocalists. In 2005 Irish boy band Westlife released their version of the song. It’s a very nice version of the song, but as you can hear, the vocals stay in a much narrower range.

#24: “Hurt” (2006)
Christina Aguilera
Christina Aguilera is one of the most prolific singers in the biz. 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.

#23: “Crawling” (2001)
Linkin Park
Chester Bennington was a phenomenal vocalist, and gave Linkin Park one of the most unique sounds of the 2000s. But the notes Bennington could hit isn’t really what makes the song “Crawling” a difficult song to master. Rather it’s the range of styles and techniques he employs throughout the three and a half minute track. From the softer, more melodic singing of the verses to the loud, emotional screaming of the chorus, it covers a lot of ground. You better prepare your throat if you plan on attempting this one.

#22: “Love On Top” (2011)
Beyoncé
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!

#21: “Livin' on a Prayer” (1986)
Bon Jovi
You can take our hand, but when it comes to properly rocking this track, we can’t swear to the fact that you’ll make it. Awesome 80s hairdo aside, Jon Bon Jovi powers through “Livin' on a Prayer” with some subtly impressive vocal stylings. The song might seem like a rather simple 80s rock ballad. But as many karaoke audiences know, making it through that chorus ain’t as easy as many think it is. Most guys should probably just remember that it’s all for fun and it doesn't make a difference if they make it or not.

#20: "Don't Stop Believin'" (1981)
Journey
Do not try to sing Journey's "Don't Stop Believin'" at your next karaoke party. Oh sure, it may sound like a great idea at the time, and everyone thinks they're going to be able to nail this absolute rock anthem with Steve Perry's grace and power....but it rarely, if ever works out. That's not only because Perry is one of classic rock's finest singers, but also because the performance hinges so strongly on his combination of clarity, power and range. "Don't Stop Believin'" may start off slowly with that iconic keyboard intro, but by the time the chorus finally hits, we're firmly on that spaceship into infinity.

#19: "Hello" (2015)
Adele
Speaking of "power," is there any popular female vocalist in recent memory that can compete with Adele in terms of sheer vocal strength? Not many! There's a reason that the English singer-songwriter’s music has sold millions of albums—and it's not because they’re easy to sing. Though it’s sure fun to try! Fans really seem to connect with her lyrics, honesty and passion. And it’s the delivery that really brings it all together. "Hello" is a perfect example. It’s the sort of heart-wrenching ballad that fans adore. It isn't so much the brooding intensity of the verse that makes "Hello" challenging, but rather the vocal control required to nail that epic chorus. There's just no one who does it quite like Adele.

#18: "Take On Me" (1984)
A-ha
Falsetto. Love it or hate it, many artists and groups have taken the vocal style and run with it all the way to chart success. A-Ha was one of those bands, a Norwegian export that struck it HUGE in the eighties with their colossal synth-pop hit, "Take On Me." For our money, we LOVE Morten Harket's falsetto note that he hits near the end of "Take On Me's" epic chorus. And it's even more impressive when you take into account that Harket has to climb two and a half octaves from his starting point of A. It’s these vocal gymnastics that make "Take On Me" such a challenge for even the most seasoned of vocalists.

#17: "I'll Never Let You Go" (1990)
Steelheart
The world of glam metal has historically been one of powerful and dynamic singers. Even so, there are few who can compete with the likes of Steelheart's Miljenko Matijevic, who absolutely dominates on the band's highest charting single, "I'll Never Let You Go." Again, this is a song that starts innocuously enough. Matijevic begins with a clear, mid-range verse before shooting for the stars with a crazy high note. Oh, and it only gets more stratospheric from there, as the Croatian-born singer seems to almost taunt us with how high he can actually go. Seriously, there's high, and then there's STEELHEART levels of high, the levels perfected on songs like this one, or "She's Gone."

#16: "I Believe in a Thing Called Love" (2003)
The Darkness
The spirit of classic Thin Lizzy lived on within the classic rock style of England's The Darkness, although the falsetto singing style of The Darkness frontman Justin Hawkins was probably the furthest thing from Phil Lynott's bluesy howl. "I Believe in a Thing Called Love" was The Darkness' biggest international hit, and quickly became infamous for Hawkins' trouser-pinching vocal approach. Not everyone can pull off an ultra-high falsetto with the sort of conviction Hawkins musters throughout this twin-guitar epic, but Justin nails it with style and sleaze to spare.

#15: "Chandelier" (2014)
Sia
We have two words to describe "Chandelier:" THAT. CHORUS. It's difficult to explain just how much emotion and pathos Sia packs into her performance. She pairs a comparatively subdued verse with an explosion of passion and cathartic anger. Sometimes, a singer just possesses this nebulous quality, an ability to connect with an audience with how they sing a song, not just the mechanics of how a song’s composed. Sia is an artist who not only possesses the knowledge and skill to get her vocal performance across, but also the ability to make that performance unique and incredibly difficult to replicate.

#14: "Sherry" (1962)
Frankie Valli and the Four Seasons
We mentioned falsettos earlier in our list, and there are few male vocalists who mastered this style better than Frankie Valli, lead singer of The Four Seasons. Valli made himself a legend off of his ability to control his falsetto arguably better than any other male performer of his era, showcasing the sort of control that verges on supernatural. Falsetto, by nature, can sound fragile and thin, but Valli sounds large and in charge throughout his performance in "Sherry," which is no mean feat. There's a reason why they're called "classics," after all, and The Four Seasons definitely created one of those when they recorded this gem back in 1962.

#13: "Total Eclipse of the Heart" (1983)
Bonnie Tyler
They just don't make 'em like this anymore. We're talking about the pompous (in the best possible way), extravagant and over-the-top operettas of Meat Loaf collaborator and songwriter, Jim Steinman. These were the songs about muscular men and wild women, the sort of ferocity encapsulated by Bonnie Tyler and her amazing performance on "Total Eclipse of the Heart." It's gothic, sumptuous and decadent power-balladry at its best, amplified by Tyler's gruff and breathy delivery. Seriously, when the near seven minute album version reaches its vocal crescendo, we're right there with Bonnie on the mountaintop, shielding our eyes from the eclipse as her vocals block out the sun in an epic show of power.

#12: "Earth Song" (1995)
Michael Jackson
Ok, so we all know about Michael Jackson's pedigree for classic music videos. But we admit that sometimes the singer's actual talent can get lost amongst all the visual spectacle. Not so with "Earth Song," a track meant for the King of Pop's "Dangerous" album, but which didn't get released until the 1995 album "HIStory: Past, Present and Future: Book 1". The song is a real showcase for Jackson's ability to meld and cross-pollinate genres, from operatic highs to gospel choral lows. Michael's legendary soul and power also make their presence known, of course, making this something of a forgotten classic from this iconic talent.

#11: "The Star-Spangled Banner" (1814)
Lyrics: Francis Scott Key & Music: John Stafford Smith
It's been the honor and bane of many a singer's existence: performing "The Star-Spangled Banner." The national anthem of the United States is infamously difficult to sing—even for the most accomplished performer—because of how much control it takes to navigate its range of key changes. The key is to start low and to conserve energy, saving a big burst of power for the anthem's climax. This is easier said than done, of course, with many great singers tripping up at either the performance side of things, or something as simple as remembering the lyrics! We're not gonna fault anyone for failing at "The Star-Spangled Banner," though, because it is a massive challenge.

#10: "Bridge over Troubled Water" (1970)
Simon & Garfunkel
The world of folk might not be the first place you might look for a stratospheric vocal performance, but don't sleep on Simon & Garfunkel. If you do, you'll be missing out on one of the all time greatest vocal achievements: the incredible "Bridge Over Troubled Water." Paul Simon wrote the song, and delivers some excellent backing harmonies, but "Bridge Over Troubled Water," at its core, is a showcase for Art Garfunkel. It's the sort of vocal that builds from a place of quiet contemplation into an emotive explosion—assisted by a perfect storm of string arrangements, incredible production and session backing from drummer Hal Blaine. We dare you not to get caught up as Garfunkel sails away on that last high note.

#9: "Wuthering Heights" (1978)
Kate Bush
Kate Bush possesses an extraordinary voice and progressive visual style, which earned her acclaim from both fans and critics. "Wuthering Heights" serves as Bush's biggest hit, and for good reason, as it sets on full display all of the singer's incredible vocal range. The song has been recorded twice by Bush, and both versions are melodic masterpieces that hinge on Bush's soaring vocals, from the song's sparse intro right on through to the booming chorus. Finally, Bush lets it rip alongside the song's lead guitar-accompanied outro, proving her place as a member of art rock royalty with a performance that still evokes chills today.

#8: "Unchained Melody" (1965)
The Righteous Brothers
"Unchained Melody" was written in 1955, and has been performed by a number of different artists over the years. It's the version recorded a decade later by The Righteous Brothers that has since gone on to become the definitive version, however, thanks largely in part to Bobby Hatfield's soaring vocal performance. "Unchained Melody" actually starts off quite slow and somber, but Hatfield soon kicks things up with a level of emotion that is completely raw and delivered with unbelievable passion. Oh, and once the drums kick in around the two minute mark? Forget about it; there isn't a dry eye in the house.

#7: "Dream On" (1973)
Aerosmith
A good power ballad can be a wonderful thing, and once in a while it can even define a band's career. Proof of this can be seen in that of Aerosmith’s, who scored a massive, iconic hit with this track from their 1973 self-titled debut. "Dream On" is another slow burn of sorts, a sensitive song composed in F minor that reaches a crescendo a little past the halfway mark as Steven Tyler's measured vocals duel with Joe Perry's lead guitar. Tyler's powerful scream serves as the linchpin of "Dream On," a gold standard against which many other classic rock singers have been measured.

#6:"All by Myself" (1996)
Celine Dion
The next song on our list has a long history of cover versions, after its original artist, Eric Carmen, adapted it from a Rachmaninoff concerto in 1975. Carmen's "All By Myself" is still remembered fondly today, but it's Celine Dion's 1996 version that is even more vocally impressive: she hits an immensely powerful high note shortly before the three minute mark, turning what was initially a great pop song into a tour de force for the French-Canadian singer to shine. Trust us when we say that you probably don’t want to attempt this one at karaoke.

#5: "Bohemian Rhapsody" (1975)
Queen
There are many reasons why Queen's "Bohemian Rhapsody" is an incredibly difficult song for just about anyone to sing. For starters, it's composed in multiple keys, and shifts styles and tempos from a ballad arrangement, to operatic accompaniment and straight up hard rock. Then, there's the nature of the vocals, which consist of all four members of Queen layering their tracks in the studio to create a larger-than-life atmosphere. There are high falsettos, deep basses and hard rock screams to tackle, all combined by lead singer Freddie Mercury and company. Simply stated: Mercury was an inimitable vocal talent, and only the bravest singers should even attempt at laying their stamp on this one - or “The Show Must Go On” for that matter.

#4: "And I Am Telling You I'm Not Going" (1982)
Jennifer Holliday
Power. This is perhaps how best to describe "And I Am Telling You I'm Not Going," a key song from the Broadway hit "Dreamgirls." The song earned Jennifer Holliday a Tony and a Grammy Award in 1982 for her absolutely inspiring performance, while Jennifer Hudson would also score a hit with her take on the film version in 2006. The tune is incredibly difficult for even the most seasoned singer to perform, as it never lets up for a second, demanding range, tone and, yes, POWER to give "And I Am Telling You I'm Not Going" the justice it deserves. Luckily, Holliday had all of these qualities and more, delivering the vocal performance of a lifetime.

#3: "Lovin' You" (1975)
Minnie Riperton
Minnie Riperton was the OG when it came to striking gold with this sort of approach, as evidenced by "Lovin' You" and its chart-topping success back in 1975. The song is backed by a sunny keyboard performance from Stevie Wonder, while Riperton sings a sweet ode to love and sex that hits the stratosphere when she hits those famous whistle notes. Fun fact: Minnie Riperton is actually Maya Rudolph's mother, and can be heard singing her daughter's name during the outro on unedited and album versions of the track.

#2: "I Will Always Love You" (1992)
Whitney Houston
We're not taking anything away from the absolutely killer original version of "I Will Always Love You," recorded by country legend Dolly Parton in 1973. For many, however, it's the arrangement Whitney Houston used for the 1992 film "The Bodyguard" that serves as the most well-known. Houston used Linda Ronstadt's 1975 cover as a basis for her version, yet she ultimately makes it her own, thanks to an incredible vocal performance. Houston's uncanny ability to balance vulnerability and power not only makes "I Will Always Love You" a stone cold classic, but it also served as a defining, pivotal moment of Houston's career as one of the great, all time singers.


#1: "Emotions" (1991)
Mariah Carey
It's not an exaggeration to describe Mariah Carey as one of the foremost vocal talents of her generation. Her prowess as a singer has been well-documented over a career that has spanned over thirty years, including such hits as "Vision of Love," "Honey" and "Hero." "Emotions" might be the ultimate Mariah Carey jam, however, one that showcases the singer's uncanny ability to reach glass-shattering high notes. The song is also a great example of the sort of light and breezy R&B that dominated charts in the ‘90s, yet is punctuated by Carey's charm and charisma. Meanwhile, her vocal histrionics steal the show from any pretender who might lay claim to her throne.


Which of these songs is your go-to in the shower? Let us know in the comments.