With all the fuss about Tom Waits’ new tour, I remembered that he worked on the “One From the Heart” soundtrack with Crystal Gayle :dubious: . Yep, he dueted with Mrs. “Don’t It Make My Brown Eyes Blue”. Then I remembered an even wilder collaboration–in 1992, Michael Bolton recorded a song called “Steel Bars” that he’d cowritten with Bob Dylan :eek: :eek: :eek: ! What other odd artist pairings do you remember? And does anyone know how either of those collaborations got off the ground?
David Bowie and Bing Crosby singing Little Drummer Boy
I know Waits is friends with Francis Ford Coppola, the director of One From the Heart, and appeared in at least two of his other movies, The Outsiders and Rumble Fish. I don’t know how Crystal Gayle got involved, though.
Robert Plant and Alison Krauss
Didn’t Eminem do a duet with Elton John?
Tiny Tim & Brave Combo? The amazing polka band from Denton, Texas, backed Mr Tim on his final album. It’s not bad–for Tiny Tim.
Brave Combo have won 2 Grammys for Polka albums, but they also play “rumba, cha-cha-cha, choro, samba, two-step, cumbia, charanga, merengue, etc.” And they rock. If Brave Combo come to your town–go & hear them!
Conway Twitty and the Residents (on Youtube, but I regret I can’t offer a link to it on my work computer)
Wildman Larry Fischer, a mentally ill man originally discoverd singing on the street by Frank Zappa, and Rosemary Clooney (who herself had suffered from mental illness and was admirably motivated to lessen its stigma) did a duet produced by Barnes and Barnes (of the earworm song “Fish Heads,” and one Barnes of which was Billy Mummy, who played Will Robinson on “Lost in Space.”)
african bambatta and James Brown? Or James Brown and Jackie Chan?
The children’s song, I Need a Nap, by Kate Winslet and Weird Al Yankovic. You can hear a sample here
Back in 1992? I saw the Indigo Girls at a concert at Colby College. Good show.
Special guest that night was Siouxsie Sioux.
I lived in Denton for about eight years. Brave Combo is fantastic. 
That’s the one I thought of, too. I don’t like either performer (and that’s putting it generously), yet this album was actually quite good.
I think the Eminem with Elton John thing was just a publicity stunt - they performed together at the Grammys, after Eminem had been accused of being homophobic (and I’m sure it didn’t hurt Elton John’s street cred, either).
Tammy Wynette and KLF, “Justified and Ancient”. I love the song, but it’s even more of a weird combo than Crosby and Bowie.
Def Leppard and Tim McGraw ("Nine Lives’). Ain’t too bad.
Al has also collaborated with Wendy Carlos.
Eminem and Elton John just performed a duet, but Elton did sing on a posthumous Tupac Shakur track… Not sure how 'pac would have like that one.
First thing that sprung to my mind was Shirley Bassey and the Propellerheads.
Cliff Richard and the cast of The Young Ones singing Living Doll.
Nick Cave and Kylie Minogue - Where the Wild Roses Grow.
And, most creepy of all - **Natalie Cole **and her late father **Nat King Cole **doing a very forgettable version of Unforgettable “together”.
I once heard a CD with a bunch of duets that Ray Charles did with various other singers/musicians. Probably the most, er, unexpected collaborator on the CD was Willie Nelson.
Goes to show how many different fields of music Ray Charles dabbled in and appreciated, I guess.
Hanson and Andrew WK
In that video Andrew mostly is shown from the back…but with all the hair you couldn’t really see him anyway.
