An iconic performer known for his timeless classics, Sinatra left an indelible mark on the world of music. But while many of his greatest hits come from the Great American Songbook, Frank Sinatra Christmas songs hold a special place in the hearts of many.
The crooner’s contribution to the festive season may be undeniable, yet he surprisingly released only four Christmas albums in his illustrious career.
On top of that, one of the most beloved Christmas songs associated with him wasn’t even originally intended to be a holiday song – it was composed during a heatwave – and doesn’t mention “Christmas” in its lyrics!
Stay tuned for that, and all more, in our roundup of some of the best Frank Sinatra Christmas songs of all time…
Written by Irving Berlin for the 1942 musical film “Holiday Inn,” the song became a standalone favourite and has been covered by many artists over the years.
Bing Crosby recorded it first, and it was released in December 1941, becoming one of the most popular versions. Another rendition was performed by Frank Sinatra in a recording in November 1944, which was released the following month just in time for the festive season as a 78rpm single with an orchestra under the direction of Axel Stordahl.
Featuring Sinatra’s smooth voice and a wonderful ballad tempo, the music captures the essence of the type of Christmas that everyone would wish to enjoy.
As with “White Christmas,” “Jingle Bells” was also recorded in 1944. The arrangement is very formal, although Sinatra does manage to inject a little light swing into the delivery of the vocals.
The harmonies and precision of the backing vocals, while impeccably executed, stop the momentum that began with Frank’s verse and chorus. Ol’ Blue Eyes is, of course, faultless.
The two songs above were released as a collection of 78rpm discs, and also as 10” LP entitled Christmas Songs by Sinatra by Columbia in 1948.
Let It Snow! Let It Snow! Let It Snow!
Not released on any of the singer’s albums of the time, the song was only released as a single. The song, written by lyricist Sammy and composer Jule Styne, was composed in Los Angeles during a heatwave in 1945 and doesn’t actually mention Christmas at all in the lyrics. However, due to its association with winter and colder weather, it became a holiday classic.
This version of the song was orchestrated and arranged by Axel Stordahl, who had become Sinatra’s preferred arranger at the time, and it was recorded five years after the original recording by Vaughn Monroe.
As usual, Frank resists the urge to sing this straight, but his timing and phrasing are impeccable, and his love of jazz shines through, adding a little swing to the proceedings.
The Christmas Waltz
This, and the songs below, all come from the 1957 album, “A Jolly Christmas From Frank Sinatra,” released by Capitol Records. This is Sinatra’s first full-length Christmas album and features the versions of the songs most widely associated with the singer. The arrangements were by Gordon Jenkins, and backing vocals were provided by the Ralph Brewster Singers.
Another tune that Sinatra relishes from the pen of Sammy Cahn and Jule Styne, he makes the 3/4 waltz time of the song sound just as it should, and the accompanying backing vocals sit well with Sinatra’s delicate rendition.
Mistletoe And Holly
On this lovely tune, Sinatra takes co-composer credits along with Hank Sanicola and Dok Stanford.
The arrangement by Jenkins opens with plucked strings from the orchestra, and the orchestration is not overcomplicated, but a sparse and clever arrangement allows Sinatra’s voice to command the attention.
This simplicity in the arrangement continues throughout, and even the contribution of the backing vocals does not permit any oversentimentality. Such is the appeal of the song that Capitol Records released it as a single in the latter part of 1957.
Have Yourself A Merry Little Christmas
First performed by Judy Garland for the film soundtrack of “Meet Me In St. Louis,” Sinatra recorded this Hugh Martin and Ralph Blane song a couple of times. His first was in 1947 and released as part of “Christmas Songs by Sinatra” the following year.
Recorded a decade later, our favourite version is much more assured, with Sinatra’s measured rendition truly captivating. The relationship with the singers sounds natural as they provide a quietly effective backdrop.
I’ll Be Home For Christmas
This is another Frank Sinatra Christmas song recorded after Bing Crosby, but do not think for one moment that this means that Frank was following in the other man’s shadow.
As good as Crosby’s 1943 version is, Sinatra totally owns this song. As is so often the case, the tempo is just right, and although very slow, Sinatra handles it with ease. He manages to imbue the lyrics with additional poignancy, enhancing the meaning of the song tenfold in the process.
The Little Drummer Boy
From the 1964 album, “12 Songs of Christmas” (Frank Sinatra, Bing Crosby, and Fred Waring), Sinatra only sings on five of the selections, and these are in collaboration with Bing Crosby and/or Fred Waring.
Sharing credits with Fred Waring & His Pennsylvanians on this song, Sinatra again makes the most of a simple yet effective arrangement for the vocalists.
His voice is at its peak, and his almost hushed delivery is paced and timed to perfection. It’s hard to imagine anyone hearing this rendition of Katherine Kennicott Davis’s composition, originally titled “Carol of the Drum“, not to be moved by the performance.
Davis’s original manuscript is set as a chorale with the melody line for soprano voice and counterparts for alto, tenor, and bass providing the parts for harmony and the drum. Frank Sinatra and Fred Waring & His Pennsylvanians achieve this magnificently.
I Heard The Bells On Christmas Day
This is a truly majestic piece of music performed again by Sinatra with Fred Waring & His Pennsylvanians.
Based on a poem by Henry Wadsworth Longfellow in 1863 titled “Christmas Bells,” the text was first set to music in 1872 and has subsequently been recast by other composers over the years.
This version by Sinatra and Waring uses a melody written by composer Johnny Marks, with the choir’s truly uplifting singing and Sinatra’s voice sounding strong and full of passion, making it a fitting setting for Longfellow’s text.
Whatever Happened To Christmas?
In 1968, Frank Sinatra recorded his last Christmas album and did so as a family affair in “The Sinatra Family Wish You A Merry Christmas.”
The album was intended to feature Frank with his children, Frank Jr., Nancy, and Tina, in different combinations. The music is at its best on the tracks that feature Ol’ Blue Eyes, but the surprise track and gem of the album is this song penned by Jimmy Webb.
A delightful ballad, beautifully orchestrated, and with some fine backing vocals from The Jimmy Joyce Singers, Sinatra has rarely had someone write a string arrangement quite as sumptuous as this before, and Frank repays the compliment with a sublime performance.
These timeless Christmas songs by Frank Sinatra continue to capture the holiday spirit and bring joy to listeners year after year.