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8 May-December Duets to Play Now

Veteran artists and younger musicians are sharing the mic — with chart-topping results

spinner image Tony Bennett and Lady Gaga; Dolly Parton and Kelly Clarkson; Olivia Rodrigo and Billy Joel
(Left to right) Tony Bennett and Lady Gaga; Dolly Parton and Kelly Clarkson; Olivia Rodrigo and Billy Joel
Kevin Mazur/Getty Images for ViacomCBS; John Locher/AP Photo; Kevin Mazur/Getty Images

Elton John and Britney Spears have had countless hits on their own, so it shouldn’t be too surprising that their first collaboration, “Hold Me Closer,” has soared to No. 1 in dozens of countries since its release last month.

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While “May-December” duets are nothing new, a wave of new ones have cropped up lately. A few worth hearing:

Britney Spears (40) and Elton John (75), “Hold Me Closer” (2022)

​Spears’ first song in six years, the track signifies a comeback for the pop star as well as a yellow brick road of sorts for younger fans who may not be familiar with the original “Tiny Dancer,” released more than 50 years ago, in 1971. 

Why it’s a good match: This upbeat, modern take on John’s “Tiny Dancer” lets both voices shine and gives longtime fans of both artists a new reason to celebrate.

In their words: “I’m just crossing my fingers that this will restore her confidence in herself to get back into the studio, make more records and realize that she is bloody good,” John told The Guardian. Upon hearing news of its No. 1 status, Spears tweeted she was “about to have the best day ever.”

Dua Lipa (27) and Elton John (75), “Cold Heart” (2021)

​Before the Britney duet, John and 27-year-old pop star Dua Lipa scored a hit with this clubby mash-up of his hit songs “Sacrifice” and “Rocket Man.”

Why it’s a good match: Few artists are as of the moment as Lipa. “Cold Heart” sounds both refreshing and warmly nostalgic.

In their words: “‘Rocket Man’ is my driving song, it’s my shower song. It’s my song I sing along to myself,” Lipa said on The Late Show With Stephen Colbert. “When I got asked to sing that part, I was, like, ‘OK, it was just meant to be.’ ” John has said he wants to record one duet each year “for a fun, happy summer record.” So far he’s two for two.

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Dolly Parton (76) and Kelly Clarkson (40), “9 to 5” (2022)

​Though the new version of Parton’s 1980 hit won’t be released until Sept. 9, a preview can be heard in the trailer for Still Working 9 to 5, a new documentary about the challenges women face at work. Notes the film’s codirector, Camille Hardman: “This version is just a little bit melancholic — that women are still trying to get equality, and it hasn’t happened yet, 42 years after this song was created.”

Why it’s a good match: While one could argue Dolly and anyone is a good match, Clarkson brings a new perspective (and has actually covered it before).

In their words: During an appearance on The Kelly Clarkson Show, Parton told her collaborator, “I love how you took that and just made it your own — and I got a chance to sing background for a change.”

Ronald Isley (81) & the Isley Brothers and Beyoncé (41), “Make Me Say It Again, Girl” (2022)

​After more than eight decades making music, the Isley Brothers found a way to top themselves again: by releasing a song featuring Beyoncé. “Make Me Say It Again, Girl” marks the first collaboration between the legendary R&B group and Queen B, and it appears on the Isley Brothers’ forthcoming record. The soulful remake puts a new spin on a track they first released in 1975.

Why it’s a good match: The song exemplifies how the musicians are still at the top of their game — and is just icing on the cake for Beyoncé in the midst of her spectacular renaissance.

In their words: “It is a whole redefinition of the song that many people will be hearing for the very first time,” Ernie Isley told Billboard. “And this new version is the mountaintop.”

Billy Joel (73) and Olivia Rodrigo (19), “Uptown Girl” (2022)

​When Rodrigo joined Joel onstage at Madison Square Garden last month, it was a complete surprise, even though her admiration of the singer has been well documented. After singing her own “Deja Vu,” which includes a reference to Joel and “Uptown Girl,” the pair launched into Joel’s 1983 hit.

Why it’s a good match: The energy coming from Joel and Rodrigo is contagious, and the duet feels free and spontaneous, which isn’t easy to do at MSG.

In their words: After the performance, Rodrigo posted on Instagram that the night was “the biggest honor ever” and she was “still crying.”

Dionne Warwick (81) and Chance the Rapper (29), “Nothing’s Impossible” (2021)

​The unlikely duet from Warwick and Chance the Rapper came about after Warwick tweeted, “Hi, @chancetherapper. If you are very obviously a rapper, why did you put it in your stage name? I cannot stop thinking about this.” Chance responded, and a friendship and collaboration followed, with the song benefiting their two charities, Hunger: Not Impossible and SocialWorks.

Why it’s a good match: It seems like not even the artists themselves saw this coming, which makes hearing them perform together even more of a delight.

In their words: When Variety asked about the collaboration, Warwick’s answer was simple: “If I see someone on Twitter I want to know more about, I ask them.” Chance’s mother, Lisa Bennett, tweeted that she was a “very Proud Ma” after hearing the duet.

Tony Bennett (96) and Lady Gaga (36), “Cheek to Cheek” (2014) and “Love for Sale” (2021)

​These two have set the standard for May-December duets in recent years, releasing two full albums of covers that include beloved songs like “Anything Goes,” “I Can’t Give You Anything but Love,” “It’s De-Lovely” and “I Get a Kick Out of You.” Highlights include their joyful rendition of “The Lady Is a Tramp,” which appeared on Bennett’s 2011 album Duets II and kicked off their work together.

Why it’s a good match: These two bring out the best in each other, and it shows. Lady Gaga electrifies jazz standards that Bennett’s fans love, and the crooner seems to get a kick out of belting out verses alongside her.

In their words: On The Late Show With Stephen Colbert, Lady Gaga spoke about recording “Love for Sale” after Bennett was diagnosed with Alzheimer’s. “When jazz begins, this man lights up in a way that is such magic,” she said.

Metallica and Joseph Quinn (28), “Master of Puppets” (2022)

​Season 4 of Netflix’s Stranger Things marked a second life for two ’80s hits: Kate Bush’s “Running Up That Hill” and Metallica’s “Master of Puppets,” originally released on the band’s 1986 eponymous album. On the show, character Eddie Munson performs the song during a pivotal moment. In real life, fans have gone wild for a behind-the-scenes video of actor Joseph Quinn jamming with Metallica and a TikTok video where the band “duets” with Eddie. The latter clip has been viewed more than 13 million times.

Why it’s a good match: Without spoiling anything, Eddie Munson’s “Master of Puppets” scene is one of the most exciting in the series. To see Metallica embrace it only elevates their appeal.

In their words: “It’s an incredible honor to be such a big part of Eddie’s journey and to once again be keeping company with all of the other amazing artists featured in the show,” Metallica posted on Instagram.

Whitney Matheson is a contributing writer who covers popular culture. The founder of USA Today’s prizewinning Pop Candy blog, she has contributed to Slate, The Hollywood Reporter and ET Online, and wrote the children’s book We Make Comics.

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