Bizarre Musical Pairings
Music is the only world where two people who otherwise wouldn’t be caught in the same room together can stand side by side like soul mates — at least for three minutes and 20 seconds. Some of the best (and, admittedly, worst) music has been made by people who probably don’t even know each other’s last names. Call them arranged marriages. Call them the brainchild of an overzealous manager. Call them the last “Hail Mary” pass for a career about to take its last gasp. Take a look at these genius and misguided pairings and then decide who you want to accompany you on your next karaoke night.
GALLERY: See all of our bizarre musical pairings.
Elton John & Eminem
In the great struggle for gay equality, you can look to Elton John and Eminem’s 2001 Grammy Awards performance as a turning point. Under pressure from the Gay and Lesbian Alliance Against Defamation (they didn’t dig some of his lyrics), Mr. Mathers agreed to an arranged marriage with Mr. John, performing his single “Stan.” The union was a success. Still, Elton and Eminem broke up the next day.
Jonas Brothers & Stevie Wonder
My God, what insane, tone-deaf music publicist put this train wreck together? The ’tween hacks were matched with Stevie at the 2009 Grammy Awards telecast for a rendition of “Superstition.” Are you kidding me? “SUPERSTITION”? A song that has more chords and changes than the entire Jonas Brothers catalog? The final nail in the coffin occurred when one of those Jonas dudes yelled, “Show ’em what you got, Stevie!” before Wonder took a solo. I'm grinding my teeth just thinking about it.
David Bowie & Bing Crosby
This is the Holy Grail of bizarre musical pairings. The two singers recorded “Peace on Earth/Little Drummer Boy” in 1977 for Crosby’s TV special, “Bing Crosby’s Merrie Olde Christmas.” Bowie has said the only reason he did it is because his mom was a fan. Unfortunately (or thankfully, depending on who you ask), there would be no future collaborations. Bing died less than two months after recording the special.
Ben Folds & William Shatner
While recording side project Fear of Pop, Folds asked Shatner to perform vocals on the track “In Love.” It was the first time Shatner had done a studio recording since his famed 1968 release, “The Transformed Man.” The two became fast friends and made a full album together in 2004, “Has Been.” They upped the oddball ante by inviting Henry Rollins, Joe Jackson, and Aimee Mann to participate.
Jack White & Loretta Lynn
Who would have thought that a 69-year-old country singer and an eccentric 29-year-old Detroit musician would make such a natural duo? As odd as the pairing may seem, it resulted in 2004’s “Van Lear Rose,” the coal miner’s daughter’s best record in years. Lynn called White her “friend forever” and took home a 2005 Grammy for Best Country Album.
Crystal Gayle & Tom Waits
In 1982 Francis Ford Coppola made an experimental musical called “One from the Heart.” The film was a financial and critical failure, but it did introduce beatnik Tom Waits to straight-laced country singer Crystal Gayle. It was a little like “Beauty & the Beast,” but it worked. Waits got an Academy Award nomination for his score.


Now lets pretend that the guitars the Bro's played didn't even make a sound, and that the Jonas dudes [no offence to the poster] were there just for show.
Wouln't that be bizzare? But then again, no one would be stupid enough to do something like that right? Right??...
but, in all seriousness, these people are going to start covering (murdering) Dylan songs or something of this nature, and that will be a sad day for real musicians everywhere.
And lately the Grammys are littered with this kind of stuff -- it usually doesn't work.
really creeped out by it. Super creeps, indeed. Makes my hair stand on end just remembering it.