10. "Bridge Over Troubled Water" - Simon and Garfunkel
Not necessarily one you'd think of, "Bridge Over Troubled Water" won many awards for being the best record of the year and was labeled an "American anthem." This song was sung so emotionally and honestly by Garfunkel that many actually believed him to have written it, contributing to the difficulty of the song - you could pull off a semi-decent rendition of it, but at the end of the day, you'll always be in Garfunkel's shadow.
9. "Samson" - Regina Spektor
Perhaps a lesser-known about entry, Regina Spektor has been cited as a storyteller through her songs, with "Samson" being a perfect example of this. Not only do you have to combat jumps of over an octave from the word "go," but you have to subdue the delivery of the song to convey the anger and sadness behind it, whilst pulling of a performance of biblical proportions. Even the slightest mistakes are instantly noticeable in this deceptively difficult song and unless you have the voice for it, it's not one I'd recommend trying.
8. "It's the End of the World As We Know It" - R.E.M.
With the longest title of the list, you should only really expect something difficult to sing. The verses of the song take absolutely no breaks, so breathing is undoubtedly an issue here. Not only that, but you'll really annoy fans of R.E.M. by performing such a poor cover of such a classic song, even if there's over six-hundred words in the space of three and a half minutes. So, you know, no pressure.
7. "Dreams" - The Cranberries
Remember this one? Cranberries' frontwoman Dolores O'Riordan has been cited as having one of the quirkiest, most interesting voices in the music industry. With a strong Limerick accent and a soft, lilting tone, even going into the first few almost-falsetto notes of this classic Cranberries' track are difficult, which rather unhelpfully sets you up for a plenitude of weird voice breaks and yodeling moments later on in the track. A pleasure to listen to, a pain to sing.
6. "Cry Baby" - Janis Joplin
The Janis Joplin version of this song became more popular and much more intensified than its' predecessor. Janis Joplin's just someone who, no matter which song of hers you pick, you really can't sing, and this song is no exception. Balancing out the powerful, driven notes with those emotionally-stricken, pained ones is not something that's easy to do. This song holds a certain cultural significance to it, too - it was released posthumously by an American legend, so unless you really can nail it - don't try it.
5. "Woodstock" - Joni Mitchell
From someone who performed at Woodstock to someone who wishes they did, both Joni and Janis were born in the same year and are both considered voices of a generation. "Woodstock" became more popular by Crosby, Stills, Nash & Young, but it's Mitchell's original version that earns a place here. Written in the uncomfortable key of Eb minor, "Woodstock" hits a barrage of beautiful, high notes, especially towards the end, where the song slows down considerably to display a number of vocal trills at falsetto-pitch. Added on to this, the singer should encapture the original feel of the legendary "Woodstock" festival without losing their way.
4. "Barracuda" - Heart
If you can find a decent cover of this, I'd like to see it! "Barracuda" became Heart's signature song for all the right reasons - it was heavy, loud and angry - and difficult to sing. Ann Wilson has been labeled as being one of the "top heavy metal vocalists of all time," and "Barracuda" - a song with numerous big notes juxtaposing with the short, quick ones - displays this perfectly. Not only that, but trying to add too much vibrato to those huge notes or overdoing them will lead to a very uncomfortable performance. This song encourages you to take everything you've learned about singing and throw it out of the window.
3. "Take On Me" - A-ha
An '80s Norwegian synthpop track really shouldn't work, but it just does. With a speed of 170 beats per minute (the fastest on this list), you really shouldn't expect to be in for an easy time with this one. The chorus hits lows of A2 and highs of E5 - a two and a half falsetto octave jump - and if that wasn't enough, each of these notes lasts a full bar, meaning you'd be struggling for any room to breathe. In short - with or without any experience, you're screwed.
2. "(I Would Do) Anything For Love" - Meat Loaf
When the shortest version you can find of a song is well-over five minutes, you know you're in for a difficult time. Perhaps this is cheating, as there's not one singer but two, though that's not to say this song is easy. With changes in time signature, key signature and tempo, even completing this masterpiece is a challenge in itself, never mind how you finish it - and even if you can finish it, you'll likely be seen as a karaoke pub singer trying to emulate Meat Loaf. If you want to enjoy yourself with a song, go for it. But if you want to show off your vocal range and capabilities, this should not be your first choice.
And number one is...
1. "It's Oh So Quiet" - Björk
Bet you weren't expecting this! I know Björk didn't originally write or record the song, but it's her version that's always cited as the best. This musical masterpiece has many changes in tempo, changes in key, and drastic changes between long, sustained notes and short, sharp ones. Added on to this, there's big, random shrieked exclamations added in the chorus of the song and towards the end. What's even worse, though, is that Björk has a vocal range better than that of Mariah Carey, spanning five (yes, five) octaves, so you really can't beat her. Oh, plus the fact that when she performs this live, she uses reverse phonation to get a dolphin-like sound effect, hitting notes usually you'd see on an oscilloscope. Performing this live is very tricky to do, and even if you master everything, Björk's versions of the song will always come out on top. It may only be three minutes, but many would argue it's three minutes too long.