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

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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

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