The Nine Worst Duets of All Time

Chris Brown and Rihanna may just have recorded a song together, but theirs is hardly the most misguided duet in music history. Here are nine of the all-time worst.

03.13.09 6:32 AM ET

Will Chris Brown and Rihanna record a song together? Reports are conflicting, but let's just say theirs would hardly be the most misguided duet in music history. Here are nine of the all-time worst.

William Shatner and…William Shatner

Whether William Shatner was in on the joke of this 1978 cover of Elton John’s “Rocket Man”—from the split screen Shatner-versus-Shatner to the irony of the Star Trek guy singing “Rocket Man”—doesn’t stop this solo duet from boldly going where no man should ever go again.

Michael Jackson and Eddie Murphy. No, Really.

It’s difficult to understand why Eddie Murphy’s singing career didn’t take off. He collaborated with Michael Jackson on this 1993 song, “Whatzupwitu,” and taped an accompanying music video that’s filled with animated hearts and what appears to be a cadre of dancing bellhops. Actually, that makes it pretty easy to understand.

Celine Dion Meets the Ghost of Elvis

The King may have left the building, but his hologram has remained behind to sing a duet with…Celine Dion? Having the technology available is not reason alone to do something, as this post-mortem duet—a 2007 performance from American Idol—so aptly proves.

Yo! Sylvester Stallone and Dolly Parton, Y’all

Did you know Sylvester Stallone could sing? Trick question—he can’t. That doesn’t stop him from teaming up with legendary Dolly Parton on this single from their 1984 movie Rhinestone.

Bono Gets Under Sinatra’s Skin

Frank Sinatra’s cover of Cole Porter’s “I’ve Got You Under My Skin” gets an update when Bono joins Ol’ Blue Eyes for the 1993 “Duets” album. Worth hearing only to remind you just how good Sinatra was—and how bad Bono was during his Zoo TV phase.

Rob Lowe and Snow White Don’t Do Mary Proud

It’s difficult to imagine what John Fogerty could possibly have done to deserve this performance. From the 1989 Oscars, the worst-ever performance of “Proud Mary.”

Rosie and Liza Present the Great “Yikes” Way

In this performance from her one-night-only 2008 prime-time variety show, Rosie O’Donnell pairs up with Liza Minnelli to sing “City Lights.” The two doyennes of Broadway high-kick their way through a cheesy, high-energy performance that makes Cats look tame in comparison.

Milli Vanilli Is Just Plain Silli

It’s hard to say which is worse: Milli Vanilli’s hit single “Girl You Know It’s True”—or the fact that they just lip-synched it.

Tough Guys Don’t Sing—or At Least These Two Shouldn’t

One has certain expectations of the exemplars of American manhood, among them that they will not do song-and-dance numbers. Or as Homer Simpson said of this Clint Eastwood and Lee Marvin duet from 1969’s Paint Your Wagon, “Aw, why did they have to screw up a perfectly serviceable wagon story with all that fruity singing?"