Frank Sinatra and Elvis Presley
> Song: Witchcraft/Love Me Tender
In 1960, ABC aired “The Frank Sinatra Timex Special: Welcome Home Elvis,” to celebrate the return of Presley from his military service in West Germany. As part of the program, the two sang a medley of one of Sinatra’s biggest hits and one of Presley’s, trading verses. Women in the audience crazy screaming whenever Elvis opened his mouth, attesting to his massive popularity at the time. In Sinatra’s own early days of stardom, women did the same for him.
Herbie Hancock and Trey Anastasio
> Song: Gelo No Montanha
In 2005, Hancock released his 45th studio album, “Possibilities,” featuring a range of pop artists including John Mayer, Christina Aguilera, Paul Simon, Sting — and the leader of psychedelic jam band Phish, Trey Anastasio. Their track, whose title is Portuguese for “Ice on the Mountain, a ballad featuring Anastasio’s guitar, won a Grammy nomination for Best Pop Instrumental Performance.
Iggy Pop and Ke$ha
> Song: Dirty Love
Iggy Pop has always been known for an experimental style and for rocking the boat. Labeled the Godfather of Punk, he founded the influential band The Stooges and collaborated with David Bowie in West Berlin in the 1970s. Singer and rapper Ke$ha had numerous Billboard Hot 100 hits in the 2010s that would still be a hit with the right crowd today. She brought Iggy on to her third studio album, “Warrior,” to record this track for an exciting mix of genres.
John Cale and Terry Riley
> Song: Church of Anthrax (album)
John Cale was a founding member of the Velvet Underground and Terry Riley is a composer best known for his minimalist works. The two combined their talents for this mostly instrumental art-rock album. Riley plays keyboards and soprano saxophone, while Cale handles keyboards and various string instruments.
Lil Nas X and Billy Ray Cyrus
> Song: Old Town Road
The track that holds the record for longest amount of time ever in the No. 1 slot on Billboard’s Hot 100, “Old Town Road” was a sensation, combining country and hip-hop for a unique sound. When the track met resistance from the conventional country music world, Cyrus — father of Miley Cyrus and known for his 1992 country megahit “Achy Breaky Heart” — jumped on the remix to give the song unmistakable country credibility The song was remixed several more times with Young Thug, Mason Ramsey, and BTS, and launched Lil Nas X’s flourishing music career.
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