David Bowie & Bing Crosby and Tony Bennett & Amy Winehouse: What Do These Pairs Have in Common

Tony Bennett & Amy Winehouse

It seems like every singer over a certain age has released a CD of duets in the last ten years, usually sharing the microphone with singers decades younger. Think Tony Bennett and Jerry Lee Lewis.

At my most cynical, I think of an old Saturday Night Live sketch, in which Joe Piscopo impersonates Frank Sinatra recording an album of duets with younger, hipper singers in an attempt to reach a younger audience. Piscopo as Sinatra calls the album, “Frank Sings Tunes the Young People Will Enjoy.”

While I think there’s some truth to the sketch, I nevertheless love the results of one such duet: Body & Soul performed by Tony Bennett and the late Amy Winehouse. Although Bennett is not a performer I seek out—he’s a little too smooth for my taste, his music too “easy listening”—pair him with Winehouse, whose voice crackles with warmth, and you’ve got a great duet. She brings her distinctive voice and edge and tension to the song, which was her father’s favorite, and when she and Bennett harmonize, the contrast of their voices and the way their voices rise and dip above and below one another is bewitching.

Fact is, duets done right can be sublime, and given the inherent drama of two people singing to one another, it’s no surprise that some of the best were written for musical theater. My musical theater favorite is One Hand, One Heart from West Side Story, sung by the characters Tony and Maria. With Bernstein’s gorgeous chord changes and soaring melodies and Stephen Sondheim’s lyrics, One Hand, One Heart is one of those songs that takes music--and the listener--to new heights. It’s been recorded by everyone from Barbara Streisand and Johnny Mathis to cast members of Glee, but I’ll stick with the Original Broadway Cast Recording with Carol Lawrence and Larry Kert.

Another lovely duet is The Sea of Heartbreak, recorded by Roseanne Cash and Bruce Springsteen for Cash’s album The List. Roseanne’s father, Johnny Cash, recorded the song, as did Don Gibson in the 1960s, but it makes for a perfect duet with Cash and Springsteen. Both of them capture the longing in the lyrics, and Bruce practically croons on this song—in a good way. (For some reason, singing on other artists' records often brings out his prettiest singing, whether he’s singing with Roseanne Cash or Roy Orbison.)

Some other great duets are:

You Mean So Much to Me performed by Southside Johnny and Ronnie Spector on the album I Don't Want to Go Home (which DPPL cardholders can download for free via Freegal).

You Can Close Your Eyes performed by James Taylor and Carole King, a show-stopper in the documentary Troubadours: The Rise of the Singer-songwriter. (But to hear their performance in full, check out Carole King’s CD Live at the Troubador.)

Sweet Jane performed by Maria McKee and Bono.

And while it’s not a personal favorite, for sheer weirdness I have to mention The Little Drummer Boy/Peace on Earth performed by David Bowie and Bing Crosby.

What's your favorite duet? Or what two singers would you most like to hear perform together? (I'd most like to hear Bruce Springsteen and the amazing Maria McKee, who in a better world would be better known.)