8 Music Collaborations Nobody Expected That Produced the Best Work of Both Careers

Some of the most enduring moments in music history weren’t planned. They happened when two artists from completely separate worlds decided, for whatever reason, to make something together – and what came out the other side surprised everyone, including the artists themselves. The list below isn’t about celebrity cameos or label-engineered crossovers. These are genuine creative unions where both parties raised their own game. In each case, the collaboration didn’t just produce a hit. It produced something that now sits near the very top of what either artist ever made.

Run-DMC and Aerosmith – “Walk This Way” (1986)

In 1986, hip-hop group Run-DMC covered “Walk This Way” in collaboration with Aerosmith, releasing it as the lead single from Run-DMC’s third album, Raising Hell. Before this track dropped, rap and rock lived in totally separate worlds, and MTV barely played hip-hop. Aerosmith’s career had also started to fade.

When producer Rick Rubin persuaded rap sensation Run-DMC to join forces with Aerosmith, no one could have anticipated what a game-changing moment it would be. There was reportedly an initial lack of enthusiasm among both parties, with concerns about reputation, but the result was a rap and rock masterpiece that some argue birthed an entirely new genre, directly informing bands like Rage Against the Machine, Linkin Park, and Eminem. The song reached number four on the Billboard Hot 100, becoming the first rap single to reach the top ten, and helped revitalize Aerosmith’s career, which had been in decline in the early 1980s.

David Bowie and Queen – “Under Pressure” (1981)

Not only was Bowie one of the greatest musicians and songwriters in history, he was also one of the great collaborators – able to produce his best while working with another artist and create a platform for them to meet him at peak performance. Under Pressure is a masterpiece, quite simply two geniuses in Freddie Mercury and Bowie meeting each other at the very top of their game.

The song stands as a true masterpiece that defies description, and the fact that both artists were at the pinnacle of their craft resulted in a moment of pure artistic mastery. To appreciate the full genius of the collaboration, you only need to listen to the acapella recordings of the vocals, recorded in the small hours of a 1979 night in New York. Even without the music, the result is spine-tinglingly magnificent.

Robert Plant and Alison Krauss – “Raising Sand” (2007)

Raising Sand is the first collaborative studio album by rock singer Robert Plant and bluegrass-country singer Alison Krauss. The genesis of the record came during a Lead Belly tribute at the Rock and Roll Hall of Fame, where the two singers performed together for the first time. Nobody saw a full album coming, let alone what it would become.

On February 8, 2009, the album won all five awards for which it was nominated at the 51st Grammy Awards: Album of the Year, Best Contemporary Folk/Americana Album, Record of the Year for “Please Read the Letter,” Best Pop Collaboration with Vocals for “Rich Woman,” and Best Country Collaboration with Vocals for “Killing the Blues.” The album met with critical acclaim, earning an average score of 87 from reviews compiled by Metacritic. The sessions involved a fascinating role reversal, with Plant tackling Krauss’s trademark bluegrass while she embraced the bluesy style that penetrates his solo work.

Taylor Swift and Bon Iver – “Exile” (2020)

“Exile” is a song by Taylor Swift featuring Bon Iver, from Swift’s eighth studio album Folklore. Depicting an imaginary narrative of two estranged lovers in an unspoken dialogue, the track is a minimal but cinematic indie-folk ballad with gospel, orchestral and chamber pop elements, combining Swift’s honeyed vocals and Vernon’s deep baritone into a melancholic duet propelled by a plodding piano, swirling strings, and soaring harmonies.

Upon release, “Exile” garnered widespread critical acclaim, with emphasis on the duo’s vocal chemistry, the agonizing lyricism, rich instrumentals and bleak atmosphere. The song also became Bon Iver’s highest-charting song and first top-ten song in all of the countries in which it charted. Folklore itself received widespread critical acclaim for its emotional weight and intricate lyricism, with critics regarding its sound as a bold reinvention of Swift’s artistry.

Lady Gaga and Tony Bennett – “Cheek to Cheek” (2014)

Lady Gaga had built her fame on outrageous pop anthems and theatrical performances. Tony Bennett had been singing jazz standards since before her parents were born. Pairing them together seemed more like a publicity stunt than a serious musical project. Critics were skeptical, audiences were curious, and then the album dropped. “Cheek to Cheek” won the Grammy for Best Traditional Pop Vocal Album in 2015, silencing every doubter.

Gaga’s vocal restraint and genuine warmth surprised everyone who expected flashy pop energy. Bennett, ever the professional, brought elegance and class. Together they introduced jazz to millions of younger listeners who had never paid attention to the genre before. Though Bennett delivered a strong effort, it was Gaga who drew significant praise, with Bennett himself believing she was destined for superstardom.

Rihanna, Kanye West, and Paul McCartney – “FourFiveSeconds” (2015)

Three names that should never logically appear on the same song: Rihanna, Kanye West, and Paul McCartney. Yet “FourFiveSeconds” managed to feel completely natural, almost like a campfire song that happened to involve three of the biggest names in music history. The acoustic guitar-driven track stripped away every expectation each artist carried with them.

Released in early 2015, it became one of the year’s most talked-about releases. McCartney’s classic songwriting instincts, Kanye’s rhythmic presence, and Rihanna’s effortless vocal delivery blended into something refreshingly simple. In a world of overproduced pop, the song’s quiet confidence was its greatest strength and biggest surprise. It remains the first and only track to bring together all three cross-generational hitmakers.

Christina Aguilera and A Great Big World – “Say Something” (2013)

Christina Aguilera had built her career on enormous, show-stopping vocal performances. So when she joined A Great Big World on “Say Something,” the biggest surprise was how little she sang. Her restraint on the track was the most powerful vocal choice she had made in years, and it worked beautifully.

The minimalist piano ballad about loss and letting go became a worldwide hit and won a Grammy for Best Pop Duo/Group Performance in 2015. A Great Big World’s understated delivery set the emotional tone, and Aguilera honored it completely. The pairing made sense in retrospect, but almost no one predicted a pop powerhouse known for big belts would do her most affecting work by pulling back. Sometimes holding back says more than belting ever could.

Post Malone and Ozzy Osbourne – “Take What You Want” (2019)

Post Malone built his brand on blending genres, but teaming up with Ozzy Osbourne was still a bold move. Ozzy, rock royalty since the 1970s, brought his signature growl to a track that also featured Travis Scott, making it one of the most genre-diverse songs of 2019. The result was surprisingly cohesive and genuinely hard-hitting, with younger fans discovering Ozzy through Post Malone’s audience while longtime rock fans grudgingly admitted the track worked.

Ozzy’s vocal performance felt energized and alive, silencing concerns about his health at the time. The song introduced two very different fan bases to each other in the best possible way. For Ozzy, it was a moment of genuine reinvention. For Post Malone, it was proof that his instinct for finding the right voice for a track was as sharp as anything in his catalog. Younger fans discovered Ozzy through Post Malone’s audience, while longtime rock fans grudgingly admitted the track slapped.

What ties all eight of these together isn’t genre, era, or even commercial success. It’s the fact that in each case, the collaboration pushed both artists somewhere they wouldn’t have reached alone. The best musical partnerships don’t dilute what each person brings. They amplify it.