Duets You Never Want To Hear

poetinahat

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Corey Hart and ZZ Top, singing Sunglasses at Night, Arrested for Driving While Blind
 

poetinahat

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The Righteous Brothers and King Missile, singing You've Lost That Detachable Penis

Sir Mix-A-Lot and the Cramps, singing Baby Got Goo Goo Muck
 
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ShapeSphere

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Jacques Brel and The Jam, singing My Death, Going Underground

George Gershwin and Paris Hilton, singing An American in Paris Hilton
 

Priene

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Iron Maiden and Kelis - Bring your milkshake to the slaughter
 

poetinahat

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Johnny Cash and Phil Collins - A Boy Named Sussudio
 

Priene

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Nat King Cole and Doves - Get your kicks on (the M62)
 

alleycat

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Stephen King and The Hollies.

Carrie Anne

You lost your charm as you were aging
Where is your magic disappearing
 

SirOtter

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Astrud Gilberto and Neil Diamond - The Girl From Ipanema Will Be a Woman Soon


The Beatles and the Fugs - Give Peace a Chance; Kill For Peace

King Crimson and Johnny Rivers - 21st Century Schizoid Secret Agent Man
 

SirOtter

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The Sons of the Pioneers and the Capitols - Cool Water Jerk
 

SirOtter

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Three Dog Night and Bette Midler and the Dave Clark Five - Black and White and Red All Over
 

~*Kate*~

brings the random.
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I've been wracking my brain trying to think of something to add, but I have to credit my mother with this one:
John Denver and Vanessa Hudgens: Rocky Mountain High School Musical
 

Higgins

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Jacques Brel and The Jam, singing My Death, Going Underground

George Gershwin and Paris Hilton, singing An American in Paris Hilton

George was dead by the time the Movie came out so it's
Oscar Levant and June Alison...uh...well that's horrible enough, but they do this thing
where they sing to each other
over the radio while Jimmy Stuart slowly freezes to death in a crashed B-36E in Alaska.
They had to shoot that 30 times because Jimmy kept sneezing.
 
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Higgins

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Three Dog Night and Bette Midler and the Dave Clark Five - Black and White and Red All Over

Nice...and then there's Nick Dale and Dick Drake trying to straighten out who gets to do what with which guitar.
 

ChunkyC

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The Beatles and the cast of the original Broadway show singing Tax Man of La Mancha.

PS -- fargin' great game, Row-Bear!
 

ChunkyC

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Led Zeppelin and Belinda Carlisle singing Stairway to Heaven is a Place On Earth.

Freddie Mercury and George Gershwin playing Bohemian Rhapsody in Blue.
 

SirOtter

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Nice...and then there's Nick Dale and Dick Drake trying to straighten out who gets to do what with which guitar.

Or just carry this game another step, combine the two of them into Dick Dale and let him handle it in his own inimitable manner. :D
 

SirOtter

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Fats Waller and Marty Robbins - Your Feets Too Big Iron
 

SirOtter

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Big Brother and the Holding Company and the Rolling Stones - Piece of my Heart of Stone

The Animals and the Moody Blues - San Francisco Nights in White Satin

War and Bruce Springsteen - Slippin' Into Darkness on the Edge of Town
 

SirOtter

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John Prine and the Beach Boys - Pretty Good Vibrations
 

regdog

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Ozzy Osbourne and John A Lomax Mama I'm Comin' Home On The Range
 

regdog

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Jeff Golub and The Who Mister Magic Bus