Frank Sinatra and Christmas are an inseparable duo, much like mistletoe and mulled wine. While he recorded the album Christmas Songs By Sinatra in 1948, it wasn’t until the late 1950s that Sinatra truly became synonymous with the festive season and its accompanying cheer. His return to seasonal recordings with 1957’s A Jolly Christmas From Frank Sinatra solidified his status as a Hollywood star and one of the most sought-after entertainers globally. This album, a masterful blend of popular festive tunes and traditional carols, cemented Sinatra’s reign as the king of the holidays, setting a conceptual standard that many artists have emulated since. He released two more Christmas albums: 12 Songs Of Christmas in 1964, featuring guest appearances from Bing Crosby and Fred Waring, and The Sinatra Family Wish You A Merry Christmas in 1968. Despite these later releases, his impact from A Jolly Christmas… was so profound that his best Christmas songs continue to define the holiday season over half a century later.
This curated list explores the 20 most beloved Frank Sinatra Christmas songs, showcasing the timeless appeal of his holiday music.
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The Top Christmas Tracks
20: A Baby Just Like You
Released in 1975 as a standalone festive single, “A Baby Just Like You” is a poignant storytelling ballad focused on universal themes of love and peace. Co-written by the renowned American singer-songwriter John Denver, this track features a lush, string-heavy arrangement produced by Don Costa.
19: The First Noel
Sinatra’s rendition of the traditional English Christmas carol “The First Noel” is imbued with a profound sense of gravitas, enhanced by Gordon Jenkins’ elegant string arrangement. The song builds progressively, culminating in rich choral passages performed beautifully by The Ralph Brewster Singers.
18: I Heard The Bells On Christmas Day
This American Christmas carol, a powerful message of peace on Earth, originated from Henry Wadsworth Longfellow’s 1863 poem “Christmas Bells.” While set to various melodies over time, Johnny Marks revitalized it with a new tune in 1956. Sinatra’s version, recorded for the 1964 album 12 Songs Of Christmas, features Fred Wesley And His Pennsylvanians.
17: The Bells Of Christmas
Inspired by the 16th-century English folk song “Greensleeves,” “The Bells Of Christmas” features lyrics by the celebrated songwriting duo Jimmy Van Heusen and Sammy Cahn. Sinatra’s recording, found on the 1968 album The Sinatra Family Wish You A Merry Christmas, is a heartwarming duet with his children, Nancy and Frank, Jr.
16: Silent Night
Originating in Austria in 1818 with music by Franz Gruber and lyrics by Joseph Mohr, this gentle carol gained significant popularity through Bing Crosby’s 1935 rendition. Sinatra recorded his version in 1945, and it later featured on his album A Jolly Christmas From Frank Sinatra.
15: An Old Fashioned Christmas
Following his departure from Capitol Records to establish his own label, Reprise, in 1960, Sinatra released this wistful interpretation of Sammy Cahn and Jimmy Van Heusen’s nostalgic song on his first Yuletide album for the label, 12 Songs Of Christmas.
14: The Christmas Waltz
Accompanied by the harmonious vocals of The Ralph Brewster Singers, Sinatra delivers a deeply affecting rendition of this often-overlooked gem, penned by Jule Styne and Sammy Cahn. Arranged and conducted by Sinatra’s long-time collaborator Nelson Riddle, the song was a highlight of his second festive album, A Jolly Christmas From Frank Sinatra.
13: Whatever Happened To Christmas
This contemporary Christmas song, penned by the then-emerging songwriter Jimmy Webb, showcases Sinatra embracing a more modern festive tune. The arrangement, featuring a celestial choir, was masterfully crafted by orchestrator Don Costa, a frequent Sinatra collaborator.
12: Christmas Memories
Characterized by lush strings and a choir, this 1975 non-album single was written by the acclaimed songwriting duo Alan and Marilyn Bergman and arranged and produced by Don Costa.
11: The Little Drummer Boy
Written in 1941 by Katherine Kennicott Davis, “The Little Drummer Boy” gained widespread recognition in the 1950s. Sinatra’s atmospheric rendition, recorded with Fred Waring & His Pennsylvanians for 12 Songs Of Christmas, offers a uniquely captivating take on this classic tale.
10: White Christmas
Sinatra’s 1944 recording of Irving Berlin’s iconic “White Christmas,” arranged by Alex Stordahl, achieved significant chart success. He later revisited the song for Capitol with Nelson Riddle and performed a memorable duet with Bing Crosby on the 1957 US TV special Happy Holidays With Bing And Frank.
9: Winter Wonderland
Originally recorded for a radio broadcast in 1949, Sinatra’s vibrant and committed performance of “Winter Wonderland” wasn’t publicly released until 1994 on an expanded edition of Christmas Songs By Frank Sinatra. His heartfelt delivery brings even the most lighthearted material to life.
8: Mistletoe And Holly
This cheerful Christmas song, co-written by Sinatra himself with Dok Stanford and Hank Sanicola, features a playful pizzicato string introduction and smooth vocals by The Ralph Brewster Singers. Recorded in July 1957, it was released as a single by Capitol.
7: I’ll Be Home For Christmas
Sinatra’s rendition of “I’ll Be Home For Christmas,” a song by Kim Gannon and Walter Kent intended to highlight the plight of soldiers serving overseas, is characterized by its slow, somber tempo and sensitive delivery. While Bing Crosby first recorded it in 1943, Sinatra imbues the song with his own poignant yet hopeful interpretation.
6: I’ve Got My Love To Keep Me Warm
Although it doesn’t explicitly mention Christmas, Irving Berlin’s song evokes a strong wintery, Yuletide feel with its December setting and mention of snow. This upbeat swinger served as the closing track on Sinatra’s 1961 Reprise album, Ring-A-Ding Ding!
5: Santa Claus Is Coming To Town
Sinatra transformed J Fred Coots and Haven Gillespie’s popular 1934 Christmas tune into a big band swing number with his effervescent single version, arranged by Axel Stordahl. Intriguingly, it was recorded just days after Christmas in 1947. He later updated the arrangement for a swing performance with Bing Crosby on his TV special.
4: Let It Snow! Let It Snow! Let It Snow!
Axel Stordahl, Sinatra’s preferred arranger in the late 1940s and early 1950s, crafted the charts for this lively rendition of a Sammy Cahn-Jule Styne classic. Written during a Los Angeles heatwave in 1945, Sinatra recorded it five years later, releasing it as a Christmas single despite the absence of the word “Christmas.” The track achieved international success, reaching No. 6 in Hungary.
3: Jingle Bells
This joyous Yuletide standard, written by James Pierpont, was precisely a century old when Sinatra recorded it as the opening track for his 1957 album, A Jolly Christmas From Frank Sinatra. Arranged by Gordon Jenkins, the tune features jazzy harmonies from The Ralph Brewster Singers and a lightly swinging beat, with Sinatra engaging in playful call-and-response.
2: The Christmas Song
Co-written by Mel Tormé in 1945, “The Christmas Song” became a significant hit for Nat King Cole and has since been widely covered. Sinatra’s understated 1957 recording is distinguished by Gordon Jenkins’ arrangement, which subtly incorporates a pizzicato string quote from “Jingle Bells,” complemented by the soft background vocals of The Ralph Brewster Singers.
1: Have Yourself A Merry Little Christmas
Topping our list is the beloved “Have Yourself A Merry Little Christmas,” penned by Hugh Martin and Ralph Blane. Originally introduced by Judy Garland in the movie Meet Me In St Louis, Sinatra’s first recording in 1948 was a resonant, Bing Crosby-esque croon. However, his definitive take came nine years later, featuring delicate accompaniment from soft strings and an unobtrusive choir.
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These timeless recordings continue to evoke the warmth and spirit of the holiday season, cementing Frank Sinatra’s legacy as the ultimate Christmas crooner. Explore these iconic tracks and let the magic of Sinatra’s voice fill your festive celebrations.