The best unlikely duos sound, afterward, as if no one else could have stood in the other microphone. These ten still do.
10Lil Nas X and Billy Ray Cyrus – “Old Town Road” The 2019 remix took a banjo loop, a rap verse and a country chorus and held the Billboard Hot 100 for 19 weeks. The pairing looked like a meme. It behaved like a standard. Genre police lost. The song stayed.
9Jay-Z and Linkin Park – “Numb/Encore” On Collision Course in 2004, Mike Shinoda and Jay-Z stitched a nu-metal chorus to a victory lap. It should have been a corporate handshake. The crowd treated it as a hymn. Unlikely is not the same as unserious, and this one proved it in arenas.
8Tony Bennett and Amy Winehouse – “Body and Soul” Recorded for Bennett’s Duets II in 2011, it was among Winehouse’s last studio vocals. A jazz elder and a soul singer half his age met on a standard and neither blinked. The tenderness is the surprise. The tuning is the classic.
7Paul McCartney and Michael Jackson – “Say Say Say” The 1983 single, from Pipes of Peace, is two of the century’s melodic minds sharing a pop smile. They had already done The Girl Is Mine. This one is lighter, stranger, and harder to file. It topped charts anyway, because the hooks did not care about the file.
6Pet Shop Boys and Dusty Springfield – “What Have I Done to Deserve This?” In 1987 Neil Tennant and Chris Lowe handed a verse to the voice of Dusty in Memphis and let the machines glitter around her. The contrast is the song. Springfield sounds like memory. The Pets sound like the present tense. Together they made a top-ten fact.
5Nick Cave and Kylie Minogue – “Where the Wild Roses Grow” The 1995 single from Murder Ballads puts a pop star in a murder ballad and does not wink her out of danger. Minogue sings the victim. Cave sings the river. The video is a painting. The record is a classic because neither voice pretends to be the other.
4Freddie Mercury and Montserrat Caballé – “Barcelona” Written for the 1992 Olympics and released in 1987, the duet sets an opera soprano against the least modest voice in rock. It could have been kitsch. Mercury’s seriousness about her instrument saves it. When they hit the title, the city feels earned.
3Bing Crosby and David Bowie – “Peace on Earth/Little Drummer Boy” Filmed in London in September 1977 for Crosby’s Christmas special, weeks before Crosby’s death, the medley is a generation gap that decides to harmonize. Bowie reportedly disliked the drummer boy part. The counter-melody they built instead is the gift. It returns every December because the oddness worked.
2Queen and David Bowie – “Under Pressure” Mountain Studios, Montreux, 1981: a jam that became a single because neither camp would leave the room. Deacon’s bass, Bowie’s yelp, Mercury’s gospel climb. The tension is audible. So is the joy. Unlikely duos rarely leave a riff this immortal.
1Run-D.M.C. and Aerosmith – “Walk This Way” Rick Rubin put them in a studio in 1986 and forced a conversation rock radio had avoided. The 1975 riff came back wearing a new accent. Hip-hop entered the mainstream without asking to be a guest. After this, the unlikely duo was no longer a novelty. It was a method.
