Frank Sinatra and the Christmas season are inextricably linked, much like mistletoe and mulled wine. While he recorded early Christmas songs, it wasn’t until the late 1950s that Sinatra truly became synonymous with December 25th and its festive spirit. His 1948 album Christmas Songs By Sinatra was an early endeavor, but it was his 1957 release, A Jolly Christmas From Frank Sinatra, that cemented his status. Having already achieved Hollywood stardom and become one of the era’s most sought-after entertainers, Sinatra’s blend of popular festive songs and traditional carols on this album crowned him the undisputed king of the holidays, setting a standard that many artists have followed since. He released two more Christmas albums: 12 Songs Of Christmas in 1964, featuring guest artists Bing Crosby and Fred Waring, and The Sinatra Family Wish You A Merry Christmas in 1968. Though his last holiday album, Sinatra had already created a legacy; over half a century later, his best Christmas songs continue to define the season.
Explore the magic of Frank Sinatra’s holiday music with his greatest hits.
The Top 20 Frank Sinatra Christmas Songs
Sinatra’s foray into Christmas music resulted in a collection of songs that have become holiday staples. Here are 20 of his most beloved Christmas tracks:
20: A Baby Just Like You
This heartwarming ballad, released as a single in 1975, tells a story of love and peace on Earth. Co-written by John Denver, it features a string-heavy arrangement by Don Costa.
19: The First Noel
Sinatra’s rendition of this classic Victorian English carol is imbued with a sense of gravitas, enhanced by Gordon Jenkins’ elegant string arrangement and beautifully sung choral passages by The Ralph Brewster Singers.
18: I Heard The Bells On Christmas Day
Based on Henry Wadsworth Longfellow’s 1863 poem “Christmas Bells,” this American carol espouses peace. Sinatra recorded it in 1964 for the album 12 Songs Of Christmas.
17: The Bells Of Christmas
Set to the melody of the 16th-century English folk song “Greensleeves,” this track features lyrics by Jimmy Van Heusen and Sammy Cahn. It was a collaboration with his children, Nancy and Frank Jr., on the 1968 album The Sinatra Family Wish You A Merry Christmas.
16: Silent Night
Originally composed by Franz Gruber and Joseph Mohr in 1818, this Austrian carol gained popularity through Bing Crosby’s 1935 hit version. Sinatra recorded his own rendition in 1945, later including it on A Jolly Christmas From Frank Sinatra.
15: An Old Fashioned Christmas
From his first Yuletide album for his own Reprise label, 12 Songs Of Christmas, this wistful interpretation of a Sammy Cahn and Jimmy Van Heusen song showcases Sinatra’s nostalgic side.
14: The Christmas Waltz
With accompaniment from The Ralph Brewster Singers, Sinatra delivers an affecting rendition of this gem penned by Jule Styne and Sammy Cahn. Arranged and conducted by his longtime ally Nelson Riddle, the song appeared on A Jolly Christmas From Frank Sinatra.
13: Whatever Happened To Christmas
Sinatra embraced a contemporary Christmas song with this track, written by Jimmy Webb. The arrangement, complete with a celestial choir, is by orchestrator Don Costa.
12: Christmas Memories
This 1975 non-album single is framed by lush strings and a choir, penned by Alan and Marilyn Bergman and arranged by Don Costa.
11: The Little Drummer Boy
Written in 1941 by Katherine Kennicott Davis, this classic tune was given an eerily atmospheric rendition by Sinatra and Fred Waring & His Pennsylvanians for the 12 Songs Of Christmas album.
10: White Christmas
Sinatra’s 1944 recording of Irving Berlin’s iconic song, arranged by Alex Stordahl, was a US pop chart hit. He also recorded a version with Nelson Riddle for Capitol and performed a duet with Bing Crosby on a TV special.
9: Winter Wonderland
Recorded in 1949 for a radio broadcast, Sinatra’s vibrant delivery brings this song to life, demonstrating his ability to infuse even lighthearted material with heart and commitment.
8: Mistletoe And Holly
Co-written by Sinatra himself with Dok Stanford and Hank Sanicola, this cheery song features Gordon Jenkins’ charts and vocals by The Ralph Brewster Singers.
7: I’ll Be Home For Christmas
Sinatra’s slow and somber version of this song, written by Kim Gannon and Walter Kent, focuses on the plight of soldiers serving overseas. His sensitive delivery captures the song’s poignancy and inherent hopefulness.
6: I’ve Got My Love To Keep Me Warm
Although it doesn’t directly mention Christmas, this Irving Berlin song’s December setting and mention of snow give it a distinct wintery feel. It’s an upbeat swinger from Sinatra’s 1961 album Ring-A-Ding Ding!.
5: Santa Claus Is Coming To Town
Sinatra gave this popular 1934 Christmas number a big band swing makeover on his effervescent single version, arranged by Axel Stordahl.
4: Let It Snow! Let It Snow! Let It Snow!
Axel Stordahl arranged this upbeat version of a Sammy Cahn-Jule Styne gem. Though written during a heatwave, the song’s themes resonated globally, charting worldwide.
3: Jingle Bells
This jolly Yuletide classic, written by James Pierpont, was recorded by Sinatra as the opening track to A Jolly Christmas From Frank Sinatra. Gordon Jenkins’ adroit arrangement and The Ralph Brewster Singers’ harmonies create a jaunty, lightly-swinging beat.
2: The Christmas Song
Sinatra’s 1957 recording of Mel Tormé’s classic is notable for Gordon Jenkins’ arrangement, which incorporates a quote from “Jingle Bells.” The Ralph Brewster Singers provide soft background vocals.
1: Have Yourself A Merry Little Christmas
Topping the list is this beloved evergreen, penned by Hugh Martin and Ralph Blane. Sinatra’s definitive take, recorded in 1957, features soft strings and an unobtrusive choir, creating a delicate accompaniment.
Discover more of Frank Sinatra’s timeless music.