Top 10 Christmas Duets of All Time

The holidays are a time to be together sharing presents, time, laughs and song.

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The holidays are a time to be together sharing presents, time, laughs and song. In honor of a time when it’s okay to sing together like a bad episode of Glee, here are the top videos of Christmas musical duets.

1. David Bowie and Bing Crosby singing “The Little Drummer Boy”

This has become a Christmas classic since the odd couple first blended voices for the 1977 Bing Crosby Christmas special. It was a duet that almost never happened because Bowie at first refused to do it, saying “The Little Drummer Boy” was all wrong for him. A team of writers and composers retooled the song with new lyrics and a new melody for Bowie that he loved, and the rest is music history.

2. John Lennon and Yoko Ono singing “So This Is Christmas”

Okay, aside from the married couple saying Merry Christmas to each other at the beginning of the song, it’s not much of a duet. And although Yoko gets a writing credit on the song, it is doubtful she added more than approval. But the anti-war song is still powerful and important today, as proven by the fact that the John Lennon estate re-released the song with a video featuring disturbing new images of war.




3. Elvis Presley and Martina McBride singing “Blue Christmas”

This was recorded during the ’68 Comeback Special on NBC, featuring the stripped-down and acoustic Elvis Presley singing in the round with a number of recording artists. It was the No. 1 TV event of the year that gave birth to a top-10 album for the following year, and Elvis’s career was reborn.

4. Sheryl Crow and Eric Clapton singing “Merry Christmas Baby”

So many modern Christmas collaborations have come from the “A Very Special Christmas” project, a series of albums to benefit the Special Olympics. The Clapton-Crow song was performed live for the fourth album in the series at a 1999 benefit concert held by then-President Bill Clinton and First Lady Hillary Rodham Clinton.

5. Lady Gaga and Joseph Gordon-Levitt singing “Baby It’s Cold Outside”

It is bizarrely perfect that the two got together to sing this famous duet for the Live Muppet Christmas Special, with Gaga singing the part normally performed by the male vocalist. Over the years a number of weirdly wonderful duos have covered “Baby It’s Cold Outside,” including Rod Stewart and Dolly Parton, Norah Jones and Willie Nelson and Jessica Simpson and Nick Lachey, but none have the weird wonder of these two.

6. Natalie Cole and Andrea Bocelli singing “The Christmas Song”

Two incredible voices sing the Christmas Classic Live for a 2009 Holiday special. There isn’t much of a back story, but the coming together of these two voices must be shared.

7. Jimmy Fallon and Mariah Carey singing “All I Want for Christmas Is You”

This has become a running bit on Fallon's show and it is ingenious. The Roots, Fallon’s house band, pick up toy instruments and play backup to popular songs performed by the stars who made them hits. There is no bigger modern Christmas song than the Mariah Carey version of “All I Want for Christmas Is You,” and Fallon and the Roots enshrine it on YouTube forever.

8. Bing Crosby and Frank Sinatra singing “White Christmas”

The song was released 1941, 18 days after the attack on Pearl Harbor, and Americans grabbed it for comfort. Since then, it is estimated that Bing Crosby’s version of “White Christmas” is the best-selling single of all time. It is so iconic that most singers wouldn’t dare infringe on Crosby’s crooning for a duet. But Frank Sinatra isn’t most singers. This is from The Frank Sinatra Show in 1957.

9. Bruce Springsteen and Clarence Clemons singing “Santa Claus is Coming to Town”

Unlike my phillymag.com compadre Victor Fiorillo, I am a huge Springsteen Fan. One of the late, great Clarence Clemons's enduring moments is his saxophone solo and Santa impression in Springsteen’s version of “Santa Claus Is Coming to Town,” which became an instant classic. The best way to enjoy Springsteen and the E Street Bands is live. Here they are Passaic, New Jersey, in 1978 before Springsteen was buff and Clarence was in his prime.

10. The Pogues and Kirsty MacColl singing “Fairytale of New York”

This is one of the most hauntingly beautiful Christmas duets in history and wildly popular on You Tube with millions of hits. MacColl died in December of 2000, a week before Christmas. She was hit by a speeding motorboat in the waters off Mexico, after pushing her teenage son out its path. This song is her legacy.

***One bonus video

It is kind of a duet between Charlie Brown and Linus from the Charlie Brown Christmas Special. It is the scene where Linus explains the real meaning of Christmas. Enjoy.

If you want more, People Magazine also has a list of weirdly wonderful duets. Including Susan Boyle bringing Elvis back from the dead for a duet. Merry Christmas.

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  • The Silent Majority

    Nothing from Dean-o? Shame on you!!

    • Aaron Cunningham

      This is one of the worst things that ever happens on the Internet: A complaint without a solution. What classic from the Dean deserved to make this list? And what should’ve been bumped?