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Which May-December Music Collaborations Made the Most Magic?​

Whether it’s Natalie Cole and her dad or Lady Gaga and Tony Bennett, these intergenerational duets are solid gold​

Side by side images of Kelly Clarkson and Reba McEntire together on stage, Tony Bennett and Lady Gaga singing together and Frank Sinatra holding his daughter Nancy in his arms during a television special

Ethan Miller/Getty Images; Kevin Mazur/Getty Images for Park MGM Las Vegas; Martin Mills/Getty Images

(Left to right) Kelly Clarkson and Reba McEntire; Tony Bennett and Lady Gaga; Nancy and Frank Sinatra

En español

​On Oct. 1, Lady Gaga and Tony Bennett, 95, are releasing their second album together, Love for Sale, a collection of Cole Porter covers. Considering that their last collaboration, 2014’s Cheek to Cheek, yielded a Grammy win for best traditional pop vocal album, this new musical partnership is sure to be another hit. While the contemporary pop diva was born nearly six full decades after the “I Left My Heart in San Francisco” crooner, the pair has undeniable musical chemistry. They’re the latest in a long line of intergenerational duets — that includes the likes of Frank and Nancy Sinatra (81) and Ray Charles and Norah Jones — who have topped the charts and picked up Grammys. Here, nine songs that prove that, when it comes to making beautiful music together, age ain’t nothing but a number. ​​

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The song: “Tell Him” by Barbra Streisand, 79, and Celine Dion, 53 (1997) ​

The age difference: 25 years, 11 months, 6 days​

The story: When Streisand decided not to appear at the 1997 Academy Awards to perform “I Finally Found Someone,” Dion — who was already there to sing “Because You Loved Me” — pulled double duty and sang both. Babs was so taken by her rendition that she reached out, and the pair soon collaborated on this soaring power ballad, in which Streisand urges the younger singer to share her feelings with the man she loves. “‘Tell Him’ feels like the highlight of an as-yet unwritten Broadway show,” Washington Post critic Richard Harrington wrote. “Don’t be surprised if Oprah builds a whole show around this ‘girlfriend’ anthem.” Though only a modest commercial hit in the U.S., the duet charted throughout Europe, and it was nominated for a Grammy for best pop collaboration with vocals. ​

Watch it: “Tell Him” by Barbra Streisand and Celine Dion, on YouTube

The song: “I Knew You Were Waiting (for Me)” by Aretha Franklin and George Michael (1987) ​

The age difference: 21 years, 3 months ​

The story: Of all of Aretha Franklin’s world-changing singles, only two ever reached No. 1 on the charts: “Respect” and this 1987 Grammy winner for best R&B performance by a group or duo, exactly 20 years later. The music video features clips of famous duets — including Sonny and Cher (75) and Marvin Gaye and Tammi Terrell — and Franklin and Michael shared a similarly timeless chemistry. After Michael died in 2016, the Queen of Soul compared recording with him to working with producer Jerry Wexler and said of the single, “Musically, it does not grow old.”​

Watch it: “I Knew You Were Waiting (for Me)” by Aretha Franklin and George Michael, on YouTube​

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The song: “Somethin’ Stupid” by Frank Sinatra and Nancy Sinatra, 81 (1967) ​

The age difference: 24 years, 5 months, 27 days ​

The story: First recorded in 1966 by C. Carson Parks and his wife, Gaile Foote, the easy-listening ditty became a smash hit the next year with this cover by the Sinatras, which went on to be nominated for a Grammy for record of the year. It’s also the only time a song performed by a father and daughter reached the top of the charts, and it was the last Ol’ Blue Eyes single to crack the Billboard Hot 100’s top 20 — amazingly, “My Way” (1969) peaked at number 27 and “Theme from New York, New York” (1980) only made it to number 32. ​

Watch it: “Somethin’ Stupid” by Frank Sinatra and Nancy Sinatra, on YouTube


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The song: “Unforgettable” by Nat King Cole and Natalie Cole (1991) ​

The age difference: 30 years, 10 months, 20 days ​

The story: For her 1991 standards collection Unforgettable … with Love, Natalie Cole performed a “virtual duet” with her legendary father, who had died in 1965. The album and recording went on to sweep the next year’s Grammys, picking up wins for album, song and record of the year. Natalie recaptured the magic five years later when she recorded “When I Fall in Love” using old vocal tracks from her father, and the song also nabbed two Grammys. ​

Watch it: “Unforgettable” by Nat King Cole and Natalie Cole, on YouTube

The song: “Smooth” by Santana and Rob Thomas (1999) ​

The age difference: 24 years, 6 months, 25 days (between Thomas and Carlos Santana, 74) ​

The story: This megawatt collaboration between Matchbox Twenty frontman Rob Thomas and the iconic Latin rock band is one of the biggest singles of all time; in fact, in 2018, Billboard ranked “Smooth” second behind only “The Twist” as the chart’s highest-performing song ever. It won Grammys for record and song of the year and best pop collaboration with vocals, and it has become one of the most ubiquitous radio singles of the past two decades. “It went through the, ‘Hey, this is a good, cool summer jam,’ and then the, ‘Hey, we’re all sick of this song and never want to hear it again,’” Thomas joked to Rolling Stone. “And then it went through the, ‘Hey, let’s listen to that song again. I remember it. That sounds good still!’” ​

Watch it: “Smooth” by Santana and Rob Thomas, on YouTube

The song: “Written in the Stars” by Elton John, 74, and LeAnn Rimes (1999) ​

The age difference: 35 years, 5 months, 3 days ​

The story: Sir Elton’s last top-40 single in the United States (so far!) was this duo with country star LeAnn Rimes, which appeared on the concept album for his Broadway musical Aida and later Rimes’ 2002 album I Need You. Within the plot of the show, the love duet is performed by Radames, the captain of the Egyptian army, and Aida, an enslaved Nubian princess, but even without that context, it works beautifully as a soaring adult-contemporary ballad that begs listeners to sing along. ​

Watch it: “Written in the Stars” by Elton John and LeAnn Rimes, on YouTube

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The song: “Here We Go Again” by Ray Charles and Norah Jones (2004) ​

The age difference: 48 years, 6 months, 7 days​

The story: Charles first recorded his version of the country standard in 1967, and it later appeared on his posthumous album, Genius Loves Company, on which he dueted with the likes of Willie Nelson (88), Bonnie Raitt (71) and Gladys Knight (77). The album went on to rack up an astounding eight Grammys, including record of the year and best pop vocal collaboration for this duet with Jones. “I sang it right next to Ray, watching his mouth for the phrasing,” Jones later reminisced about the recording session to Billboard. “He was very sweet and put me at ease, which was great because I was petrified walking in there.” ​

Watch it: “Here We Go Again” by Ray Charles and Norah Jones, on YouTube

The song: “Me Against the Music” by Madonna, 63, and Britney Spears (2003) ​

The age difference: 23 years, 3 months, 16 days ​

The story: Spears had already fully recorded this funk-inspired dance track, before she played it for the Queen of Pop during rehearsals for the 2003 MTV Video Music Awards — where the pair famously kissed. When Madonna responded positively to the song, the producers handed it over to Madonna, who added her own vocals. Spears later said she was “beyond surprised” by how much she added to the song, and it went on to become Madonna’s 50th entry on the Billboard Hot 100. ​

Watch it: “Me Against the Music” by Madonna and Britney Spears, on YouTube

The song: “Because of You” by Reba McEntire, 66, and Kelly Clarkson (2007) ​

The age difference: 27 years, 27 days ​

The story: Clarkson had a platinum hit with this emotional single in 2004, and three years later, she paired up with the country legend for a collaboration on her album Reba: Duets. The duo got to exercise their acting muscles in the stylish music video, in which they starred as a pair of 1930s Hollywood lounge singers, though Reba would later play a very different role in the American Idol winner’s life: She was Clarkson’s step-mother-in-law from 2013 to 2020. ​

Watch it: “Because of You” by Reba McEntire and Kelly Clarkson, on YouTube

Nicholas DeRenzo is a contributing writer who covers entertainment and travel. Previously he was executive editor of United Airlines’ Hemispheres magazine and his work has appeared in The New York Times, Condé Nast Traveler, Travel & Leisure, Sunset and New York magazine.