5 of the Most Unlikely Duets

Finding the perfect duet partner can be a challenge.

While some duet partners just make sense – Ella Fitzgerald with Louis Armstrong, Michael Jackson with Paul McCartney, and Dolly Parton with Kenny Rogers – others will leave you thinking: “How in the world did those two link up?”

It’s those unexpected duets that we’re looking at today. Below, find five of the most unlikely duets of all time.

1. Dolly Parton and Sylvester Stallone – “Woke Up in Love”

Would you believe Sylvester Stallone as a country singer? Yeah…audiences in 1984 had trouble settling into that one too while watching Rhinestone. The film saw Stallone play a grouchy cabbie that was tapped by a nightclub singer (Dolly Parton) to get a Southernly transformation. In the end, Stallone’s character takes a more rock ‘n’ roll route with his music, which feels more apt for the New Yorker. Nevertheless, we were gifted this twangy duet between the actor and the country star that is so strange it almost works.

2. Nelly and Tim McGraw – “Over and Over”

The idea of a hip-hop country crossover might not seem so bonkers today in a post “Old Town Road” world, but in 2004 it was a hard sell. When Nelly and Tim McGraw teamed up for “Over and Over” they were met with some trepidation from their record labels. Nevertheless, the track reached the Top 5 on the Billboard Hot 100 chart, far exceeding the naysayers’ expectations.

“Tim was cool,” Nelly once told The Boot about this collaboration. “Obviously, when I came up with that idea to do that record, everybody wasn’t all gung-ho like they would probably say they are now, obviously seeing the success.

“I give Tim so much credit,” he continued. “[He] was still at a peak in his career where he was growing. For him to entrust in a rapper, to give this a go, you got to understand how forward-thinking he was as well, because I could probably guess that he had a few people like, ‘Yo, are you sure? What is this going to do?”’

3. Phil Collins and Bone Thugs-N-Harmony – “Home”

Samples can be a fickle thing. At times, a group will interpolate a section from a track, turning it into something that the original artist isn’t too keen on. That was not the case for Phil Collins when Bone Thugs-N-Harmony sampled a section of his track “Take Me Home” for their 2003 song “Home.”

Collins appeared in the group’s video for “Home,” joining in on the fun and sternly looking down at the camera. The track earned Collins a spot as an honorary member of Bone Thugs-N-Harmony with the moniker Chrome Bone.

4. Shakira and Blake Shelton – “Need You Now”

The Voice brought Shakira and Blake Shelton together and subsequently delivered this unsuspecting yet beautiful cover of Lady A’s “Need You Now.” Though Shelton’s country roots make him a shoo-in for this track, Shakira’s musical style couldn’t live farther away from the vocal group’s. Nevertheless, the pair’s voices meld perfectly together in this cover making for a welcomed surprise.

5. Ozzy Osbourne and Jessica Simpson – “Winter Wonderland”

Competing for perhaps the weirdest thing you will see today is this duet between Ozzy Osbourne and Jessica Simpson. The idea of Osbourne singing a Christmas song is an interesting proposition in its own right, but you add Simpson into that mix and the likelihood of it happening seems like one in a billion.

Nevertheless, the stars aligned prompting this odd couple to perform “Winter Wonderland” for The Osbourne Family Christmas Special on MTV in 2003. Osbourne’s heavily warped vocals paired with Simpson’s belt are the height of cognitive dissonance.

(Photo by L. Cohen/WireImage)