For me one I can think of immediately is "Friends In Low Places".

I mean singing the real original notes not substituting easier notes to hit. What about your hardest song to sing.
Boo

One of the toughest is Star Spangled Banner.
Don't try to get too perfect though. Garth Brooks never sings it the same way twice!
DonM

First is the Star Spangled Banner..next up for me...is Ave Maria..I was asked to sing this at a wedding next week...Big Basilica ..little me...pavarati I am NOT!!!

Hey B2

The trick to Ave Maria (from experience) is NOT to be Pavarotti. Be yourself, most couples want a more contemporary feel to their wedding music, and if you over do the operatic vocals it will sound too unnatural. Be yourself, you will do fine.

As far as the hardest song, while SSB is difficult, you can put it in the right key for you and be okay.

A hard one for me is Paul Davis' "I Go Crazy." Some really low stuff in there.

How about Love me tender[just kidding]..

I'd settle for just being able to sing lead vocals !!!

Steve

I find different songs present different kinds of vocal challenges:

1) Songs with a wide vocal range
* Star Spangled Banner

2) Songs which contain unusual musical intervals:
* I Love You, Cole Porter ( descending Maj 7th interval)
* Lush Life, Billy Strayhorn (unusual intervals)

3) Songs with off-beat or sycopated rhythms or unusual meter changes
* 'Anyone Who Had a Heart', Burt Bacharach: 4/4 & individual measures of 5/4
* 'Top Hat, White Tie, and Tails', Irving Berlin: tricky rhythm & sycopated phrasing

4) Fast tempo songs with tricky phrasing & lyrics (tongue twisters)
* 'One Note Samba', Antonio Jobim
* 'Joy Spring', Clifford Brown
* 'I've Been Everywhere', Hank Snow

I find the most taxing songs to be ones that stay in the upper range for pretty well the whole song, like Hotel California. HATE doing that song. :-)

Range wise I would have to say that songs by Mariah can be challenging as she loves to sing through her whole range in every song.

Celine Dion is probably the most difficult to sing well as she is so sickeningly perfect in her trills and dynamics that if you don't match her, you will automatically suffer in comparison.

But all in all the most difficult songs for me are ones that use any type of low falsetto. Like "How Deep is your love", "Tiny Dancer", or the last note of Meatloaf's "Heavan can wait". If my voice isn't in tip top shape than the first thing to go is my falsetto, and the low range is gonzo for sure.

I had the good fortune to sing the Star Spangled Banner at a Phillies/Mets game in 1986 at Vet stadium, and even with the HUGE echo, the 35,000 people (it was April brrrrr...)and my face on the fan-o-vision it was not as scary as the time I had to do the Ave Maria (I chose the Bach)for my cousin's wedding. The song is tough enough, but added to the mix was the fact that the bride's mother was MY godmother and a LATIN professor to boot. PRESSURE !!!!!!
My throat was dry, the room seemed dead and all I could hear was the pounding of my own heart. Terrifying. I love the song, but it's much better suited to an operatic type voice than mine.

Back to the Vet - I'm gonna miss that place. My high school band played the first Eagles game as well as the first Phillies game in that stadium. We have a long history and it's a shame to tear it down for a team that never even won the big one. Hey - I love my home teams, but a new stadium ? C'mon .... what's THAT gonna do? Just raise the prices.

Funny that the two songs that trouble me the most were already mentioned, huh? Maybe we're not all that different after all?
Thankfully, I almost never do either song at my regular jobs. Whew.

Well it seems many of us here have something in common with Billie Holiday. Ha! Ha!
Not bad company heh?

Brava - Mina, has weird intervals, Phasing, word play and range. Also very fast.

I give it to Minnie Ripperton on the high note department as more then belting one or two up there, she sang. Check out her solo stuff and even more so the Rotary connection records. That aint a synth, it's Minnie.

For me it is every thing as I suck