Best Christmas Album Ever: “A Jolly Christmas From Frank Sinatra”

Happy Birthday, Frank Sinatra! Born December 12, 1915, the greatest interpreter of modern popular song and arguably the greatest entertainer of the 20th century would’ve turned 101 today.


Sinatra, who passed away in 1998, left behind an immense and peerless body of recordings, stretching from the late 1930s to the early 1990s. And his estate has continued to release interesting new collections, like last year’s set of radio recordings and this year’s set of concerts from around the world.

In 1957, Sinatra recorded what I think is the finest Christmas album ever made, leaving us a gift that keeps on giving year after year.

I’ve had “A Jolly Christmas from Frank Sinatra” on CD for about 20 years, and I fondly recall enjoying it in Las Vegas, appropriately enough, during a December trip in the late 1990s, when I was helping with a sales launch meeting for MCI.

Sinatra was at the pinnacle—or at least one pinnacle—of his career in 1957. He had moved on from Columbia—actually, they had dropped him—and he had begun recording with Capitol, a young, upstart label based in Los Angeles, in 1953.


While he was at Capitol, the LP record format really came into its own, and Sinatra made the most of it, recording a series of concept albums that many consider among the highest achievements of his very high achieving career.

At Capitol, Sinatra worked with the industry’s best musicians and arrangers, starting out with Billy May and then teaming up with Nelson Riddle. Riddle would orchestrate most of the most iconic recordings of Sinatra’s career, including everything from “I’ve Got You Under My Skin” to “One for My Baby (and One More for the Road.)”

Gordon Jenkins, another gifted arranger who often worked on Sinatra recordings that featured choruses and strings, did the honors for this album. And he nails the orchestrations, which are both timeless and contemporary to 1957.

“Jolly Christmas” begins with a swinging version of “Jingle Bells.” Actual jingle bells are the first sound you hear, and the cool-cat arrangement perfectly matches Sinatra’s mid-1950s persona.

He doesn’t actually use his signature phrase “ring-a-ding-ding” but listen to the moment, about 90 seconds in, when he sings “jing-jingle bells” with a little hitch. You can almost see the tilted hat and knowing, charming smile.

Side A continues with “The Christmas Song,” written by Robert Wells and Mel Torme. The Voice is in very fine voice here, and this might’ve been the definitive version of the song if Nat King Cole hadn’t scored a massive hit with it a decade earlier.

Next up is “Mistletoe and Holly,” a new-at-the-time song that makes an energetic and strong debut on “Jolly Christmas.” Another swinging number featuring vibrant holiday imagery.

Sinatra is appropriately wistful on the next track, “I’ll Be Home for Christmas.” The song, which achieved great popularity during the war years, was already a seasonal standby, a dozen years after V-J Day.

The fifth track may be my favorite Christmas recording of all time: “The Christmas Waltz,” penned by Sammy Cahn and Jule Styne. (Cahn, a brilliant lyricist, would later partner with music man Jimmy Van Heusen on dozens of songs written specifically for Sinatra.)

In July of 1954, Sinatra asked Cahn and Styne to write him a Christmas song. “The Christmas Waltz” became the B-side for a Sinatra single of “White Christmas.”

In both music and lyrics, “The Christmas Waltz” perfectly expresses the romance of Christmas with lines like “frosted windowpanes, candles gleaming inside, painted candy canes on the tree” and “it’s that time of year, when the world falls in love.”

Many CD pressings of “Jolly Christmas” include the 1954 recording of the song and “White Christmas” from the same single as a bonus tracks.

Sinatra would later record yet another version of “The Christmas Waltz” at a slightly slower tempo for “The Sinatra Family Christmas” album in 1968. (That version is readily available today on “The Christmas Collection” CD of Reprise holiday recordings from 2004.)

To close out Side A, Sinatra sings “Have Yourself a Merry Little Christmas,” a song from “Meet Me in St. Louis” that’s freighted with a lot of emotion and sadness.

Frank had previously recorded the song with the original lyrics, but, as he studied the words prior to the recording sessions for “Jolly Christmas,” he didn’t feel good about singing the line “until then, we’ll have to muddle through somehow.”

Sinatra wanted something different, something that would make the song a bit less of a downer. But he couldn’t do so without the permission of the song’s lyricist, Hugh Martin.

Martin, who understandably thought his original lyric just fine, didn’t want to lose the opportunity to have the song recorded again by Sinatra—possibly generating fresh royalties—so he gamely wrote a new line: “hang a shining star upon the highest bough.”

In the nearly 60 years since, artists have recorded both the original and alternate lyrics. And even Sinatra himself reverted to the original lyric when he recorded a more melancholic and reflective version for Reprise in 1963.

For Side B of “Jolly Christmas,” Sinatra turned from popular songs to Christmas hymns, with reverent, full-throated performances of “The First Noel,” “Hark! The Herald Angels Sing,” “O Little Town of Bethlehem,” “O, Come All Ye Faithful,” “It Came Upon a Midnight Clear.” He closes the album with a lovely version of “Silent Night.”

Christmas hymns—and particularly “Hark! The Herald Angels Sing”—remind me of attending candlelight services on Christmas Eve with my family at Peachtree Presbyterian Church in Atlanta.

I always made a point of sitting next to my dear maternal grandmother, Louise Moore. I’m not sure “Ahma” was always perfectly in tune, but her singing was one of the sweetest, most beautiful sounds I’ve ever heard.

Reflecting this season on “Jolly Christmas,” I realized that one of the things that makes it perfect is the balance between holiday pop songs on Side A and hymns on Side B. In this, the album captures the essence of Christmas music and, indeed, the way we celebrate Christmas as a whole.

There is the fun and romantic side of Christmas. And there is the sacred side. “Jolly Christmas” brings them together in a single album sleeve.

In this, “A Jolly Christmas from Frank Sinatra” is every bit the concept album that he popularized with “Songs for Swingin’ Lovers,” “Come Fly With Me,” “Nice ‘n’ Easy,” “In the Wee Small Hours” and the rest.

Sinatra fans have questioned the exclusion of “Jolly Christmas” from Capitol’s box set of his concept albums. And they are right to do so.

Tonight—or some other night soon—put on a copy of “Jolly Christmas” and see what you think of it.

If you’re so moved, you might lift a glass in toast to Frank Sinatra. Enjoy your favorite tipple or try Frank’s favorite his way: two fingers of Jack Daniel’s with a couple of cubes of ice.

Let the ice melt and your heart warm to the strains of the best Christmas album in history.

A note on versions. There are many versions of “Jolly Christmas” available on both CD and vinyl. I like the bonus tracks from 1954 on the version of the CD that I own. If you have a sound system worthy of vinyl, try a new pressing of the 2010 vinyl. My buddy Larry gives it his highest endorsement. Which is good enough for me. And for you.

One Comment

  1. Having a rare lunch alone, waiting on an order of General Tso enjoying the blog! I’ve got to but this album now.

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