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Monday, June 1, 2020  Spokane, Washington  Est. May 19, 1883
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Sing with Bing: A playlist of favorite Bing Crosby holiday tunes

UPDATED: Thu., Dec. 20, 2018

We all know the image: A smiling Bing Crosby, wearing a Santa hat and a bow tie of holly leaves, looking out at us from a snow-white background.

It’s the cover image from “Merry Christmas,” the 1955 re-release of an earlier Crosby compilation. The title was changed again, in 1986, to “White Christmas,” in honor of the record’s most famous song.

Bing and Christmas go hand in hand; as Richard Corliss pointed out in a 2014 article in Time, “Bing pretty much invented the Christmas music industry. He’d been hosting Christmas specials on radio since 1936.”

(It was, in fact, on one of his radio broadcasts, Christmas Day in 1941, that Crosby would first perform the song that would come to define him.)

While “Merry Christmas”/“White Christmas,” is not just Bing Crosby’s best-known album, it’s also one of the iconic holiday albums of all times, right up there with Nat King Cole’s “The Christmas Song,” the Vince Guaraldi Trio’s “A Charlie Brown Christmas,” or Elvis Presley’s “Elvis’ Christmas Album.”

So sure, you could make a playlist that includes just the songs from the Spokane-raiseed singer’s classic LP. But during his lifetime, Crosby recorded at least seven Christmas albums and appeared on several Christmas-themed compilations, so there’s a lot more Christmas music to choose from. Below are my Top 10. You’ll find them assembled in a public playlist on my Spotify page for easy listening.

1. “Little Drummer Boy/Peace on Earth” (1977) I’m getting the controversial one out of the way first. Some people love this song. Others loathe it. I’m in the former camp. I love how weird the chemistry between David Bowie and Crosby is. I also love how good their voices sound together. Filmed for Crosby’s final Christmas special “Bing Crosby’s Merrie Olde Christmas” – Crosby died five weeks after the taping – the song would become a hit in the U.K. when it was released as a single in 1982.

2. “Mele Kalikimaka” (1950) Crosby and the Andrews Sisters were among the first to record this song by Robert Alex Anderson. It appeared on the 1955 reprint of the iconic “White Christmas” album. The song is jaunty and fun and puts me in the mood for a stroll on the beach and a seaside cocktail. There are worse ways to spend Christmas.

3. “Sleigh Ride” (1977) Crosby recorded a version of “Sleigh Ride” in 1952; that’s the version that appears on “The Voice of Christmas: The Complete Decca Christmas Songbook,” a 1998 compilation of Crosby’s Christmas recordings on Decca from 1935-56. Shortly before his death in 1977, Crosby recorded songs for an album called “Seasons,” which was released posthumously. For this project, he took on “Sleigh Ride” again, this time with a funky, 1970s smooth jazz vibe, thanks to arrangements and backing from Pete Moore and his Orchestra and the Johnny Evans Singers. His voice had lost some of its characteristic smoothness but still sounded like Bing.

4. “The Christmas Song” (1946) Yes, Nat King Cole recorded it first, also in 1946, and his 1961 recording of this Bob Wells and Mel Tormé song is iconic and perfect and glorious. But Crosby also turns in a lovely version. There are songs that simply mean Christmas, no matter who sings them. This is one of them.

5. “Silver Bells” (1950) While his good friend Bob Hope sang this Jay Livingston and Ray Evans song with Marilyn Maxwell for the movie “Lemon Drop Kid,” it was Crosby who recorded it first, with help from Carol Richards. Their voices are so lovely together.

6. “Have Yourself a Merry Little Christmas” (1962) Does this top the iconic Judy Garland version? No. But it’s such a beautiful song, and Crosby’s rich baritone sings it beautifully.

7. “I’ll Be Home for Christmas” (1943) This one might be the most important song on Crosby’s discography. Written by Kim Gannon and Walter Kent, the song reportedly was intended to honor soldiers serving overseas during World War II. Indeed, as the Library of Congress notes, the song “became the most requested song at Christmas U.S.O. shows in both Europe and the Pacific.” Crosby pours so much emotion in the song, just try to listen to it without tearing up. I dare you.

8. “Jingle Bells” (1943) Crosby and the Andrews Sisters scored a hit with their take on the winter tune by James Lord Pierpoint, published under the title “One Horse Open Sleigh” in 1857. LaVerne, Patty, Maxine and Bing turned it into a jazzy little number, complete with syncopated rhythms and a big band horn sound.

9. “Silent Night” (1947) Crosby’s voice is in beautiful form in this version of the German Christmas carol, which is celebrating its 200th anniversary this year. His 1947 recording is iconic and credited by some with bringing the song into mainstream popularity. And with 30 million copies sold, it’s also the third best-selling single of all time, behind Elton John’s 1997 release of “Candle in the Wind” and a certain other Bing Crosby holiday song …

10 “White Christmas” (1941) It’s a classic, the definitive 20th century Christmas song. The best-selling single of all time, with more than 50 million copies sold, is a perfect blend of melancholy and hope. You can imagine Crosby remembering the snow-covered winters of his Spokane youth when he croons: “I’m dreaming of a white Christmas/Just like the ones I used to know/Where the treetops glisten and children listen/To hear sleigh bells in the snow.”

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