The Ten Worst Duets in Pop History

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10. Tony Bennett and Amy Winehouse: "Body and Soul" In 2011, the classic crooner Tony Bennett paired up with a cavalcade of pop stars to record some standards, resulting in a mostly great but occasionally horrendous album, Duets II. A few of Bennett's choices are just wrong, like his rendition of "Stranger in Paradise" with adult contemporary hot shot Andrea Bocelli. But it's his version of "Body and Soul" with a slurring Amy Winehouse that is most cringeworthy. Yeah, it is Winehouse's last performance before her untimely death and, sadly, it's not that great.

9. Britney and Jamie Lynn Spears: "Chilln' with You" By now, it should be explicitly clear that Britney Spears was at best fleetingly gifted at singing or writing songs. "Chillin' with You," off her 2013 (!!) album, Britney Jean, is not her finest hour. Throughout the first half of the song, Spears sings about getting drunk in a heavily auto-tuned voice over a club beat that sounds like it was produced on a laptop at 3 a.m. by some drunk DJ. Then, things get really chill when Jamie Lynn Spears shows up for the second verse with her equally pitch-corrected whine.

8. Huey Lewis and Gwyneth Paltrow: "Cruisin'" Have you ever seen the movie Duets? The film is a real heartwarmer about competitive karaoke that stars Gwyneth Paltrow, Huey Lewis and Paul Giamatti. In a pivotal scene, Paltrow joins Lewis on stage to sing Smokey Robison's "Cruisin'," and soon, the duo is cruising right along into a hopelessly cheesy version of the Motown classic.

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Ian Gassman
Contact: Ian Gassman