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.
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.”