Top 20 Most Difficult Songs to Sing

Journey
We're kicking off our list with a little friendly advice: don't 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.

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.

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.

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."

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.

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.

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.

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.

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.

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 performance—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.

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.

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 which still evokes chills today.

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.

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.

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.

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.

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 Tonyand 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.

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.

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.

Before we name our number one pick, here are some honorable mentions!

"Sinful Passion" (2018), Dimash Kudaibergen
From Kazakhstan with Love

"Given Up" (2008), Linkin Park
Screaming & Singing Is No Easy Feat

"Listen" (2007), Beyoncé
A Soul-R&B Ballad Where the Vocals Range from F♯3 to G5

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.