The singer had a close relationship with Ozzy Osbourne, and at the 2025 MTV Video Music Awards, he performed a tribute to his late mentor. However, Yungblud is not the first to work with an artist of another generation; here are seven other iconic multi-generational collaborations.
Tony Bennett & Lady Gaga
In 2014, Tony Bennett and Lady Gaga joined forces for their collaborative album Cheek to Cheek, becoming an unexpected but beloved duo. Gaga had cemented herself as a pop superstar, known for wearing meat dresses to award shows. However, after her experimental 2013 album, Artpop, Gaga pivoted again, this time turning toward jazz music.
The two first worked together in 2011 on a cover of “The Lady Is A Tramp,” which led to their 2014 album. After much success, the two toured together and released a follow-up album, Love For Sale, in 2021, ten years after their first cover. Gaga continued making pop music, releasing Chromatica in 2020 and her big comeback, Mayhem, this year.
However, her Tony Bennett collaborations changed the trajectory of her career. Not everyone can go from being one of the biggest pop stars of the 2010s to singing jazz music with an industry legend, but Gaga proved her artistic abilities. She also earned a lot of respect for the collaboration as she pushed the boundaries for what pop stars are capable of.
While there were certainly rock influences in their track “Take What You Want,” the song was mostly trap and rap-inspired. The British singer’s vocals brought the track to life, especially toward the end, as the electric guitars kicked in. A year later, Osbourne featured Post Malone on a song for his own album.
“It’s A Raid” leaned more into rock than the rapper’s song, pushing Malone out of his comfort zone. The collaborations inspired Post Malone to further experiment with music, allowing him to move from rap into the rock and even country genres.
Dua Lipa & Elton John
Dua Lipa became an official pop superstar when she released her sophomore album, Future Nostalgia, in 2020. Incorporating disco-pop into her sound, Lipa resonated a lot with older generations who longed for the sounds of their youth.
The “Levitating” singer was happy to team up with some of the stars of the past, releasing “Cold Heart” with Elton John in 2021. The song interpolates John’s songs “Rocket Man,” “Kiss The Bride,” “Sacrifice,” and “Where’s the Shoorah?” Not only did the song build music industry credit for Lipa, but it also proved John’s ability to resonate with audiences of all ages.
The dance-pop production matched perfectly with Lipa’s sound without sacrificing John’s lyricism. Lipa has recently been performing with some other industry legends on her Radical Optimism tour, like Nigel Rogers, and her collaboration with Elton John arguably led her there.
Madonna & Justin Timberlake
When two of the biggest pop stars of their time come together, it’s indubitably a massive deal. Madonna was the biggest pop star of the 80s, and Justin Timberlake took over the 2000s after going solo. For her eleventh studio album, Hard Candy, Madonna teamed up with Timberlake and producer Timbaland for “4 Minutes.”
The song dominated the airwaves, making Madonna the center of attention again and giving Timberlake an added boost to his career. It’s arguably one of the most iconic collaborations of the 2000s.
Mariah Carey & Ariana Grande
When Ariana Grande left Nickelodeon for the pop world in 2013, she was instantly compared to Mariah Carey. The ’90s icon was not fond of the comparisons, responding, “First of all, I’m still young,” when told Grande was being called a young Mariah.
However, the two put their mostly tabloid-fueled feud behind them for a 2020 Christmas collab that changed their relationship forever. Grande appeared on a new rendition of “Oh, Santa” alongside Carey and Jennifer Hudson during Mariah Carey’s Magical Christmas Special. In 2024, Grande released her single “Yes, And?” and about a month later released a remix featuring Mariah Carey.
The two also appeared together on Barbra Streisand’s track “One Heart, One Voice.” Grande and Carey were most recently seen together when Grande presented the “Always Be My Baby” singer with the Video Vanguard Award at the 2025 MTV Video Music Awards. The collaboration helped the two overcome the comparisons, proving they could coexist and both continue to be iconic.
Paul McCartney, Kanye West, & Rihanna
An unexpected collaboration came in 2015 when Kanye West and Rihanna teamed up with Paul McCartney for “FourFiveSeconds.” The collab came out of left field, especially for West, who has stuck exclusively to rap in his career. The track was a much more stripped-down song than anything West or Rihanna had released before.
The track marked a new beginning for West, who at this point had reconciled with Taylor Swift and seemed to have the public back on his side. While it certainly didn’t last, it was still an interesting career move for him and showed the public that rappers and R&B artists should not be pigeonholed into that genre.
Dolly Parton & Sabrina Carpenter
When Sabrina Carpenter finally broke into the mainstream with her album Short n’ Sweet, the comparisons were endless. Carpenter was like a modern Marilyn Monroe, Agnetha Fältskog (of ABBA), and Madonna. However, one of the comparisons she got the most was to country icon Dolly Parton.
Carpenter played into the role, and Parton didn’t mind the comparisons either. ForShort n’ Sweet deluxe, Carpenter included a country rendition of “Please Please Please,” featuring Parton. The two sounded effortless together, and the accompanying music video made them look like a mother-daughter duo.
Parton is always one to appreciate the artists who came after her and welcome them into the industry with open arms. She did the same with Carpenter and even admitted she’d love to work with the pop star again sometime.
0 Comments