11 of the most unexpected musical collaborations of all time

In honour of Ed Sheeran’s upcoming collaboration with Cradle of Filth, here are the other duets that no one saw coming

It’s happening, everyone. Cradle of Filth front man Dani Filth has confirmed that Ed Sheeran is still working on their collaborative single.

“He’s done some of it, but then he had a baby, and he obviously got very sidetracked with that and doing whatever Ed does, which is play massive shows around the globe,” Filth said in a recent interview. “He’s not at our beck and call. But he is going to finish it, he assures me. I actually spoke to him quite recently.”

What will a Sheeran/Filth duet look like? We can’t wait to find out (although we do hope it involves Ed changing his name to Dead Sheeran, as speculated by Stereogum). In the meantime, here are eleven other musical collaborations that no one saw coming.

Ed Sheeran and Bring Me The Horizon

Ed Sheeran – Bad Habits (feat. Bring Me The Horizon) [Live at the BRIT Awards 2022]

Sheeran is known for his collaborations, but his team-up with British rock band Bring Me The Horizon still managed to surprise us. Enlisting their help on the lead single from his newest album =, ‘Bad Habits’, the singer delivered something darker than we’ve previously heard from him. Bring Me The Horizon also recently invited Sheeran to join them onstage at their Reading festival set as a surprise to fans.

Louis Theroux, Duke & Jones and Jason Derulo

Jason Derulo x Duke & Jones x Louis Theroux x Amelia Dimz - Jiggle Jiggle [Official Music Video]

When Chicken Shop Date creator Amelia Dimoldenberg asked Louis Theroux if he could recall a rap from a twenty-year-old Weird Weekends episode, neither of them could have predicted that they’d find themselves in a music video with Jason Derulo. But that’s exactly what happened after producing duo Duke & Jones got hold of the snippet and turned it into TikTok’s new favourite song, ‘Jiggle Jiggle’. Even more unexpectedly, Derulo found his way onto the music video version with a feature verse about the difficulties of digesting caviar, among other things.

David Bowie and Bing Crosby

A supremely awkward skit on Crosby’s Merrie Olde Christmas special in 1977 gave way to a surprisingly beautiful duet in which Bowie and Crosby performed a mash-up of ‘Little Drummer Boy’ and ‘Peace On Earth’ beside a piano. They weren’t the duet partners we were expecting, but the world was moved nonetheless. The recording ended up being Crosby’s final TV performance – he tragically suffered a heart attack just weeks later.

Nelly and Tim McGraw

Nelly - Over And Over (Official Music Video) ft. Tim McGraw

How did these two cross paths, you might wonder? Playing basketball, according to Tim McGraw. They got along like a house on fire and Nelly ended up pushing his label to orchestrate a collab. Although Nelly pitched the track ‘Over And Over’ to McGraw as a country song, McGraw strongly disagreed that it fit into the genre, although he told news outlets that it was good fun all the same.

Lil Nas X and Billy Ray Cyrus

Lil Nas X - Old Town Road (Official Video) ft. Billy Ray Cyrus

When Billy Ray jumped on the remix of ‘Old Town Road’, the lines between rap and country became even blurrier. One thing, however, was crystal clear – people loved it. Their successful collaboration brought the two musicians close, and Cyrus told Insider that he thought of Lil Nas as family. “I would die for that boy, I really would,” he said.

Find tickets for Lil Nas X here.

Young Thug, Elton John and Nicki Minaj

Elton John, Young Thug, Nicki Minaj - Always Love You (Official Audio)

When Young Thug sampled ‘Rocket Man’ on his 2018 track ‘High’, John sat down with the rapper to give him some career advice. He told Thug to include more melody in his rap music, believing the combination of the two to be the young musician’s best chance of success. Their working relationship developed to the point where they decided to release a track together. John has since described the experience of watching Thug freestyle in the studio on ‘Always Love You’ as “an amazing moment in my musical life”. The pair also enlisted rapper Nicki Minaj to round out the track.

Find tickets for Elton John here.

Taylor Swift and Bon Iver

Taylor Swift – exile (feat. Bon Iver) (Official Lyric Video)

When mega popstar Taylor Swift pivoted suddenly into indie folk with a surprise album, no one saw it coming. Listening through the album, fans discovered more surprises, including a duet with American indie folk band Bon Iver named ‘Exile’. The tender, folksy ballad wasn’t far out of Bon Iver’s wheelhouse, but it was worlds away from Swift’s previous sugary electropop album, Lover.

Find tickets for Bon Iver here.

Paul McCartney, Rihanna and Kanye West

Rihanna, Kanye West, Paul McCartney - FourFiveSeconds

More than anything, this single will be remembered by the amount of Twitter users calling McCartney a “random old man”. ‘FourFiveSeconds’ united three unlikely collaborators to create something that doesn’t sound like it would have appeared on any of their solo albums – which is what makes it unexpectedly great.

Jack White and Alicia Keys

Alicia Keys & Jack White - Another Way To Die [Official Video]

The theme song for the 2008 Bond film Quantum of Solace facilitated an unlikely collaboration. ‘Another Way To Die’ brought together White Stripes front man Jack White and R&B singer songwriter Alicia Keys for the first duet in Bond theme song history.

Justin Bieber and Busta Rhymes

Justin Bieber - Drummer Boy ft. Busta Rhymes (Official Audio)

The year was 2011, and 17-year-old pop star Justin Bieber had already secured a number of high profile features for his Christmas album Under The Mistletoe, including Mariah Carey, Usher and (somewhat hilariously) Boyz II Men. But he was preparing to record a duet that would top them all – ‘Drummer Boy’ with Busta Rhymes. You just have to listen to this one.

Find tickets for Justin Bieber here.

Tony Bennet and Lady Gaga

Tony Bennett, Lady Gaga - The Lady is a Tramp (from Duets II: The Great Performances)

Elsewhere in 2011, pop star Lady Gaga met 85-year-old jazz singer Tony Bennet in New York, and the two decided to record a version of ‘The Lady Is A Tramp’. Finding that they enjoyed working with each other immensely, the two went on to record not one but two albums together – 2014’s Cheek to Cheek and 2021’s Love On Sale – picking up a few Grammys for good measure.