Duets can help elevate an artist’s career in more ways than one. They show versatility, can introduce you to a totally new audience, and give you a bigger stage to show off your talents on. Here are some collaborations that were a little unexpected but that left us wanting more.
Videos by American Songwriter
“Peace On Earth/Little Drummer Boy” by David Bowie and Bing Crosby
In 1977, Bing Crosby and David Bowie did a mashup of these two Christmas classics, to everyone’s surprise. The performance was actually recorded for Bing’s television Christmas Special at the time, and it wasn’t even Bing’s idea. The duet was orchestrated by music supervisors Ian Fraser and Larry Grossman. Originally, Bowie didn’t even want to do the special, as it didn’t really align with his artistic vision. However, it was his mom, apparently, that convinced him to do it. Bing’s daughter, Mary Crosby, told The Sun, “David wasn’t going to do the show, and his mum said, ‘No, you have to work with Bing Crosby!’ She was a fan. She was like, ‘You have do this.’”
“I’ve Got You Under My Skin” by Bono and Frank Sinatra
For a crooner like Sinatra to collaborate with someone like Bono, the lead vocalist of U2, some otherworldly forces would have to be at play. I guess they were, because in 1993, this song was the first single off Frank Sinatra’s Duets album. Other duets off the project included collaborations with Gloria Estefan, Tony Bennett, and Barbra Streisand, all of which make total sense. However, the album as a whole snatched the No. 2 spot on the Billboard charts, so I guess Sinatra knew what he was doing.
“Say Say Say” by Michael Jackson and Paul McCartney
Before these two pop icons collaborated on “Say Say Say,” they had already recorded two other duets. However, this one turned out to be the most memorable of the three, scoring Paul and Michael a No. 1 hit on the Billboard Hot 100. However, even McCartney admitted that, when you listen to the song, it’s hard to tell whose voice is whose. “Particularly on the new mix,” he told James Dean Bradfield, “you can’t tell kind of thing.” Apparently, when working on the song, McCartney was trying to match the vibe of Jackson’s voice, and now, it’s hard to tell them apart.
Photo by: TV Times via Getty Images












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