11. ROY ORBISON & K.D. LANG
Orbison’s classic 1961 tearjerker seemed not only untoppable but un-mess-withable. Yet somehow, this redo with the lowercase Canadian songstress turned the song’s defining loneliness on its head, twining the pair’s voices in a soaring invocation of shared heartache.
9. TAYLOR SWIFT & T-PAIN
”Thug Story” (2009)
Kanye may have famously impugned her video bona fides, but Florida rapper T-Pain had no such qualms when he joined the princess of country-pop on this CMT Awards parody of her own hit ”Love Story” — a perfect storm of out-of-control Auto-Tune and Swift’s sweetheart charm (”What, what, I knit sweaters, yo!”).
7. THE KLF & TAMMY WYNETTE
”Justified and Ancient” (1992)
All bound for Mu Mu Land! That command, issued by the Nashville icon and a pair of British art-pop pranksters then largely unknown Stateside, was, as far as anyone could tell, a call to arms for pancultural, postmodern urban druids. Deeply weird? Yes. Glorious? Absolutely.
4. DAVID BOWIE & BING CROSBY
”Peace on Earth/Little Drummer Boy” (1977)
Whoever had the imagination to put the Thin White Duke and Mr. White Christmas in the same room, let alone on the same song, was justly rewarded. Their lovely televised reworking of a holiday classic was made even more poignant when Crosby passed away only weeks after its recording.
1. EMINEM & ELTON JOHN
Eminem was already known for his pitch-black worldview and the often-blatant homophobia in his lyrics when he released the brutal obsessed-fan murder fantasy ”Stan.” So when he chose openly gay Elton to sing the song’s hook at the 2001 Grammys, many thought that hell had in fact frozen over. And yet the matchup proved unexpectedly resonant — and the unlikely duo remain friends to this day.
Pink and Jack White? Taylor Swift and Kanye? Find out who’s on our wishlist of surprising duets.