What would be the most difficult songs in history to sing (as a cover) ?

I am not a technical singing expert by any means.

I would imagine Kate Bush's Wuthering Heights would be up there

Heart's Alone is also considered quite a difficult song to sing

A-Ha's Take on Me.

Staying Alive by the Bee Gees unless you were born with an amazing Falsetto like Barry Gibb

Snow - Informer

Bohemian Rhapsody is a tough one to pull off

The Star-Spangled Banner

Hocus Pocus by Focus.

The grammar and capitalization in the header is giving me a zetz

Anyway, aside from the melisma-afflicted pop du jour, try tackling MmmBop at karaoke. Or better yet, don't!

It's the End of the World as We Know It (And I feel fine)

Il dolce suono.

Iron Butterfly-In A Gadda Da Vida

In sixth grade, our class was singing various songs from around the world for a school show and we had to sing something called "Lady of Spain," which had a prologue with a note progression in it that none of us could master. It was this verse:

It was the bolded part that gave us the most trouble and defied us in every rehearsal. We may have gotten close to it in the final rehearsal and our teacher would have said something like, "Okay, good enough, do it like that in the show and we'll be fine." In any event, on the night of the big show, of course, we botched that verse all over again and tried to compensate by singing the rest of the friggin' song as loud as we could. During the intermission, the teacher stormed into the kindergarten classroom that was being used as our backstage rest stop and yelled at us, telling us that was the worst singing he'd ever heard. I've since listened to professional recordings of the song and even Luciano Pavarotti would have trouble with that note. Any intelligent show director working with sixth-graders would have simply changed songs or--best solution yet--cut out that freaking verse! It was totally unnecessary. There is no reason that song couldn't have started with the main verse, "Lady of Spain, I adore you / Right from the night I first saw you..." etc., etc.

I had occasion to bring this up recently with two classmates from that era (this show happened 50 years ago) and neither one could remember what the hell I was talking about.

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One more. Credeasi, Misera! without resorting to falsetto. Probably only couple handfuls have been able to sing this over the last two hundred years or so.

One Week - Barenaked Ladies

The singer himself failed when playing the song in Karaoke Revolution (I believe at E3).

Anything sung by Freddie Mercury or Roy Orbison, both had incredible range - deep to high and back again without breaking.

Any Philip Glass composition.

(Maybe not exactly what the OP had in mind).

Trying to sing and play guitar at the same time, where the singing is not written entirely in sync with the guitar lines, and/or the guitar lines are extremely technical.

Examples of the former is stuff like:

Journey - Separate Ways (World Apart), Only The Young, etc ...
Guns 'N Roses - Welcome To The Jungle
Duran Duran - The Reflex
Def Leppard - Hysteria


ie. The singer isn't also playing a guitar.

I would imagine many of Mariah Carey's songs would apply here.

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Some songs on Sanctuary's first album Refuge Denied.

https://en.wikipedia.org/wiki/Refuge_Denied
https://en.wikipedia.org/wiki/Warrel_Dane

Machine Gun Eddie is even tougher!

I've always been proud of myself for being able to nail "Semi-Charmed Life" by Third Eye Blind in karaoke a few times. I know all the words and can hit the high notes haha.

Especially while trying to hold in the laughter.