Best Frank Sinatra Christmas Songs: 20 Classics That Define The Holidays

It’s not a white Christmas without Ol’ Blue Eyes… The best Frank Sinatra Christmas songs have a unique magic that brings the holiday season to life.

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Photo: Martin Mills/Getty Images

Frank Sinatra and Christmas go together like mistletoe and mulled wine. As the best Frank Sinatra Christmas songs prove, having one without the other is unthinkable, but it wasn’t until the late 50s that Sinatra became synonymous with December 25 and all its festivities.

He’d recorded the album Christmas Songs By Sinatra in 1948, but by the time he returned to seasonal recordings, with 1957’s A Jolly Christmas From Frank Sinatra, the Hoboken-born singer had become a Hollywood star and one of the most in-demand entertainers of all time. With its blend of popular festive songs and seasonal carols, A Jolly Christmas… crowned Sinatra the king of the holidays, establishing a conceptual template that many singers have since followed.

Two more Christmas albums followed: 12 Songs Of Christmas, which was released in 1964 and featured guest spots from Bing Crosby and bandleader Fred Waring, and 1968’s The Sinatra Family Wish You A Merry Christmas. The latter was Sinatra’s final foray into Christmas songs, but he’d already done enough: over half a century later, the best Frank Sinatra Christmas songs still define the holidays.

Without further ado, here are our 20 best Frank Sinatra Christmas songs.

Listen to the best Frank Sinatra Christmas songs on Apple Music and Spotify.

20: A Baby Just Like You

This song – issued as a non-album festive single, coupled with “Christmas Memories,” on Reprise in 1975 – is a storytelling ballad whose message is love and peace on earth. It was co-written by noted US singer-songwriter John Denver with Joe Henry (later an acclaimed record producer) for his adopted son, Zachery. The string-heavy arrangement on Sinatra’s version was by Don Costa, who also produced this version.

A Baby Just Like You

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19: The First Noel

A sense of gravitas imbues the elegant Gordon Jenkins string arrangement that opens Sinatra’s rendering of William B. Sandy’s Victorian English Christmas carol. The song builds gradually, climaxing in rich choral passages beautifully sung by The Ralph Brewster Singers.

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18: I Heard The Bells On Christmas Day

This American Christmas carol, which espouses peace on Earth, was based on an 1863 poem called “Christmas Bells” by the American poet Henry Wadsworth Longfellow. It was later set to music by several different composers, but in 1956 the song was revived with a new melody by composer/lyricist Johnny Marks. Sinatra recorded this one in 1964 on the Sonny Burke-helmed album 12 Songs Of Christmas, in the company of Fred Wesley And His Pennsylvanians.

I Heard The Bells On Christmas Day

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17: The Bells Of Christmas

The 16th-century English folk song “Greensleeves” was the melodic inspiration for “The Bells Of Christmas,” which had lyrics written for it by noted tunesmiths Jimmy Van Heusen and Sammy Cahn. On his recording, Sinatra shares the microphone with his children Nancy and Frank, Jr. It featured on the 1968 Reprise album The Sinatra Family Wish You A Merry Christmas.

The Bells Of Christmas (Greensleeves)

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16: Silent Night

The history of this doleful Austrian carol goes back to 1818, when it was composed by Franz Gruber and Joseph Mohr; but they weren’t alive to reap the financial benefits of having Bing Crosby take it into the Top 10 of the US charts in 1935. Sinatra recorded his version as a Christmas single in 1945, and it later appeared on his album A Jolly Christmas From Frank Sinatra.

Silent Night (1999 Remaster)

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15: An Old Fashioned Christmas

In 1960, Frank Sinatra left Capitol to form his own record company, Reprise. This wistful interpretation of Sammy Cahn and Jimmy Van Heusen’s nostalgic song came from his first Yuletide album for the label, the collaborative 12 Songs Of Christmas.

An Old Fashioned Christmas

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14: The Christmas Waltz

Accompanied by sugar-frosted harmonies from The Ralph Brewster Singers, Sinatra serves up an affecting rendition of this overlooked gem from the pens of renowned tunesmiths Jule Styne and Sammy Cahn. Sinatra’s longtime musical ally Nelson Riddle is the arranger/conductor here, and the song appeared on Ol’ Blue Eyes’ second festive album, A Jolly Christmas From Frank Sinatra. Sinatra revisited the tune on 1968’s The Sinatra Family Wish You A Merry Christmas, featuring The Jimmy Joyce Singers And Orchestra.

The Christmas Waltz

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13: Whatever Happened To Christmas

Written by “that kid, Jimmy Webb”, as Sinatra was fond of calling the rising young songwriter in the 60s, this tune finds him embracing a contemporary Christmas song. The glittering arrangement, complete with a celestial choir, is by noted orchestrator Don Costa, who often collaborated with Sinatra in the 70s.

Whatever Happened To Christmas?

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12: Christmas Memories

Framed by lush strings and an obligatory choir, this was a non-album single from 1975 that was written by husband-and-wife songwriting duo Alan and Marilyn Bergman, and arranged and produced by Don Costa.

Christmas Memories

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11: The Little Drummer Boy

Written in 1941 by Katherine Kennicott Davis, “The Little Drummer Boy” rose to fame in the 50s via versions by The Trapp Family Singers and The Harry Simeone Chorale. Sinatra, together with Fred Waring & His Pennsylvanians – who had guested on the singer’s 1964 album America, I Hear You Singing – creates an eerily atmospheric rendition of this classic tune taken from 12 Songs Of Christmas, released later the same year.

The Little Drummer Boy

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10: White Christmas

Sinatra recorded this Irving Berlin song with an orchestra and choir (The Bobby Tucker Singers) in 1944. Arranged by Alex Stordahl, it reached No. 7 in the US pop charts and charted again in 1945 and 1946. Sinatra also recorded a version for Capitol, with Nelson Riddle at the helm, and duetted on the song with Bing Crosby on the 1957 US TV show Happy Holidays With Bing And Frank.

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9: Winter Wonderland

Recorded for a radio broadcast in 1949, Sinatra’s version of “Winter Wonderland” was not made available publicly until 1994, when it appeared on an expanded CD version of Christmas Songs By Frank Sinatra. It features some introductory words by Sinatra, who brings the song alive with his vibrant delivery, showing that he could bring heart and commitment to even to the most frivolous and lightweight of material.

8: Mistletoe And Holly

Pizzicato strings open a cheery Christmas song that Sinatra co-wrote with Dok Stanford and Hank Sanicola. Featuring on-the-money charts by Gordon Jenkins and sugar-coated vocals by The Ralph Brewster Singers, it was recorded in July 1957 and released as a single by Capitol later that year.

Mistletoe And Holly (Remastered 1999)

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7: I’ll Be Home For Christmas

A bell tolls on the intro to Sinatra’s slow and slightly somber version of a song written by Kim Gannon and Walter Kent, who wanted to focus public attention on the plight of soldiers serving overseas during the holiday season. “I’ll Be Home For Christmas” was first recorded by Bing Crosby, in 1943, but Sinatra makes it his own thanks to a sensitive delivery that is poignant but also reflects the song’s inherent hopefulness.

I'll Be Home For Christmas (If Only In My Dreams)

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6: I’ve Got My Love To Keep Me Warm

Though it never mentions Christmas directly, this song by Irving Berlin is set in December and mentions snow, which certainly gives it a wintery Yuletide feel. An upbeat swinger, Sinatra recorded it as the closing cut of his first Reprise album, the Johnny Mandel-arranged Ring-A-Ding Ding!, in 1961. The track later opened the 2004 Frank Sinatra Christmas Collection.

I've Got My Love to Keep Me Warm

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5: Santa Claus Is Coming To Town

Sinatra gave J Fred Coots and Haven Gillespie’s much-covered and hugely popular 1934 Christmas number a big band swing makeover on his effervescent single version of the song arranged by Axel Stordahl. Somewhat bizarrely, it was recorded three days after Christmas, on December 28, 1947. Sinatra updated it ten years later but kept the swing elements on a version performed on his TV special with Bing Crosby.

4: Let It Snow! Let It Snow! Let It Snow!

New York-based trumpeter Axel Stordahl, who was Sinatra’s preferred arranger in the late 40s and early 50s, wrote the charts for this upbeat version of a Sammy Cahn-Jule Styne gem that was written in July 1945 during a heatwave in Los Angeles. Sinatra recorded it five years later, releasing it as a Christmas single even though the song never mentions the “C”-word. The warm background vocals come courtesy of The Swanson Quartet. “Let It Snow! Let It Snow! Let It Snow!” charted all around the world, achieving its highest position (No. 6) in Hungary.

Frank Sinatra - Let It Snow! Let It Snow! Let It Snow! (78rpm Version) (Audio)

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3: Jingle Bells

This jolly Yuletide classic, written by New England songwriter James Pierpont, was exactly 100 years old when Sinatra recorded it as the opening track to 1957’s A Jolly Christmas From Frank Sinatra. Adroitly arranged by Gordon Jenkins on what was the first of several Sinatra sessions, the tune opens with jazzy, close-harmonies by The Ralph Brewster Singers sprinkled over a jaunty, lightly-swinging beat. Sinatra indulges in some playful call-and-response with the background singers.

Frank Sinatra - Jingle Bells

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2: The Christmas Song

Co-written by singer Mel Tormé in 1945, “The Christmas Song” was a massive US hit for Nat King Cole in 1946 and has been much covered since. Sinatra’s deliciously low-key 1957 recording of it is notable: arranger Gordon Jenkins works in a quote from “Jingle Bells,” played by pizzicato strings. The Ralph Brewster Singers provide soft background vocals.

The Christmas Song (Merry Christmas To You) (Duet)

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1: Have Yourself A Merry Little Christmas

At the top of the tree in our list of the best Frank Sinatra Christmas songs is this one, penned by Hugh Martin and Ralph Blan. A much-loved evergreen, “Have Yourself A Merry Little Christmas” was first sung by Judy Garland on the Meet Me In St Louis movie soundtrack. Sinatra first covered it in 1948, delivering the song in a resonant Bing Crosby-esque croon, but, nine years later, he recorded what’s regarded as his definitive take on the song. Soft, shimmering strings and an unobtrusive choir provide delicate accompaniment.

Have Yourself A Merry Little Christmas (Remastered 1999)

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Listen to the best of Frank Sinatra on Apple Music and Spotify.

1 Comment

1 Comment

  1. Timothy A Goldich

    December 24, 2022 at 7:55 pm

    Great list!! Nobody sings Christmas like Frank.

    Personally, I’d swap out a few of the more trivial songs (“Santa Claus Is Coming to Town”) in favor of a few missing songs of true depth, greatness, and profundity (“It Came Upon a Midnight Clear” “Oh Little Town of Bethlehem”). Some may prefer the “ring-a-ding-ding” Frank, but when the deeply Catholic Sinatra turns his attention upon a transcendent masterpiece of song craft, he transforms into a humble slave to the sacred—and without a trace of artifice. It is when he sings great art, like Ave Maria, that Frank becomes a great artist. It’s a live recording and the sound quality is not the best, but when The Voice tackles this operatically demanding masterpiece, he rises to the occasion breathtakingly.

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