Your choice for the hardest song to sing at a Karaoke Bar? Mine is "Along Comes Mary."

Wanderin' Star by Lee Marvin?

 

The original by Lucky Starr is even harder:

 

Let's see one of you microphone macho men tackle this one:

 

Anything by Roy Orbison!

Many of his songs are quite complex and start our relatively low, but end on a high note, and the worst thing is that you have to sustain that note for quite a while... Even Pretty Woman, which sounds deceptively simple to some, is quite difficult to sing, because you have to be able to hit a F#4 and not make it sound like a forced yell...

Also, don't try any of these unless you're a skilled singer (with tenor range):

Any Journey song... (Steve Perry is a high tenor)
Any Boston song... (again, Brad Delp is a high tenor)
Bon Jovi - Livin' On A Prayer (the chorus will kill you)
Bruce Springsteen - Dancing In The Dark (Bruce really belts pretty high for a baritone)

 

"Too Much Monkey Business" ~ Chuck Berry

 

A few years ago I tried to sing along when Becca Stevens did a cover of Joni Mitchell's "Help Me" live. I had to stop singing after less than 2 lines. When I mentioned it to Becca at the merchandise table afterwards she agreed that it was indeed "very hard to sing".

 

Life Is a Rock (But the Radio Rolled Me) would be quite a feat of labial-fricative dexterity...

 

I watched a very close friend attempt "My Way" once...an excellent singer, they hit all the right notes, but the swagger just wasn't there...

 

3 Days by Bare Naked Ladies

 

...Tequila

 

Jillian, over-souling it on "Comin' 'Round The Mountain" (1:08; borderline work-safe)
Jillian at Karaoke - Workaholics (Video Clip) | Comedy Central

<that is how you get it done

 

I tried singing Stevie Wonder's "Send one your love" at a Karoake bar in Japan..And really struggled with it..Tough song to sing!

 

Porpoise Song

 

Elis Regina - Bala Com Bala

 

Please…don’t sing ‘My Way’, ‘Frank’s’ way!

If a vocalist’s performance of another artist’s song could qualify as an oxymoron, I’d have to say that song would have to be ‘My Way’.
I get it, if one is gonna pick someone’s vocal style to emulate that’s not in the Rock arena, why not aim for Sinatra, right?
If while the intro is vamping during Karaoke or Talent Night, you mention that you’re doing a ‘tribute’ to Frank, that I can understand and fully accept…case closed.

But if you chose that particular tune because you’d like that song’s powerful lyrical statement to be your final self-testimonial, ya’ may want to consider varying the phrasing and maybe consider substituting the exact notes of the melody just ever so slightly here and there, to may make it sound just a wee-bit more believable….

 

Barry Jive and The Uptown Five do a fine version of it in ' High Fidelity '.

 

I had a hard time with Revolting Cocks cover of Da Ya Think I'm Sexy

 

Frank Sinatra - My Way

 

'Weasels ripped my Flesh' - Frank Zappa

 

Here we go ( deep breath ) :
" Bee B Bumble and the Stingers , Mott the Hoople , Ray Charles Singers , Lonnie Mack and Twangin' Eddy . Here's my ring we're goin' steady........................................Aretha!...............Listen they're playing ' our song....celebrate , celebrate dance to the music....wooo"

 

The Led Zeppelin's Black Dog is a toughy. I've seen it done with unintentionally hilarious results. Wailing like Robert Plant ain't easy.

 

Bridge Over Troubled Water - good freakin' luck with that sustained note by Garfunkel at the end.

 

Yeah, written by an Aussie bloke named Geoff Mack, who gave it to Lucky, who prior to the record was a rock n roller, known for his custom Star shaped guitar, but hadn't had any substantial hits. This one was a huge one in '62 down under and put him on the path to doing more 'Novelty' type discs.

 

I couldn't carry a tune on a flatbed truck, sober. I'd have to be plenty likkered up to attempt karaoke.