Frank Sinatra’s name is practically synonymous with Christmas. To many, the festive season simply isn’t complete without the velvety voice of Ol’ Blue Eyes serenading us with yuletide classics. While Frank Sinatra recorded Christmas Songs By Sinatra early in his career in 1948, it was really in the late 1950s that his association with December 25th truly solidified, making him a cornerstone of Christmas celebrations for generations to come.
By the time Sinatra revisited holiday recordings with 1957’s A Jolly Christmas From Frank Sinatra, he had ascended to Hollywood royalty and become one of the most sought-after entertainers in the world. This album, a masterful blend of beloved Christmas carols and popular seasonal tunes, cemented Sinatra’s status as the undisputed king of Christmas music. It laid the groundwork for a concept that countless artists have emulated ever since, aiming to capture that same festive magic.
Following the success of A Jolly Christmas, Sinatra further graced us with two more Christmas albums: 12 Songs Of Christmas in 1964, featuring collaborations with Bing Crosby and Fred Waring, and The Sinatra Family Wish You A Merry Christmas in 1968. Although the latter marked his final dedicated Christmas album, Sinatra’s contributions to the genre were already monumental. Even now, more than half a century later, the best Frank Sinatra Christmas Songs remain definitive, essential listening for the holidays, evoking warmth, nostalgia, and timeless Christmas cheer.
So, without further ado, let’s unwrap our list of the 20 best Frank Sinatra Christmas songs, each a gem in the crown of holiday music.
20: A Baby Just Like You
Released as a standalone single in 1975, coupled with “Christmas Memories,” this heartfelt ballad speaks of universal love and peace, a sentiment perfectly suited to the Christmas season. “A Baby Just Like You” was penned by the celebrated singer-songwriter John Denver with Joe Henry, initially as a song for Denver’s adopted son, Zachery. Sinatra’s rendition, arranged and produced by Don Costa, features a rich, string-laden orchestration that amplifies the song’s tender message.
19: The First Noel
Opening with an air of reverence, Sinatra’s interpretation of this classic Victorian English Christmas carol, originally by William B. Sandy, is elevated by Gordon Jenkins’ elegant string arrangement. “The First Noel” gradually builds in intensity, culminating in powerful choral sections beautifully rendered by The Ralph Brewster Singers. Sinatra’s vocals bring a sincere and heartfelt quality to this timeless carol, highlighting its spiritual core.
18: I Heard The Bells On Christmas Day
This poignant American Christmas carol carries a powerful message of peace, born from Henry Wadsworth Longfellow’s 1863 poem “Christmas Bells,” written during the American Civil War. While various composers have set the poem to music, it was Johnny Marks’ 1956 melody that revived the song’s popularity. Frank Sinatra recorded this version in 1964 for the album 12 Songs Of Christmas, produced by Sonny Burke, featuring the accompaniment of Fred Waring And His Pennsylvanians. Sinatra’s delivery underscores the song’s yearning for peace amidst strife, making it a resonant Christmas message.
17: The Bells Of Christmas (Greensleeves)
Taking melodic inspiration from the traditional 16th-century English folk song “Greensleeves,” “The Bells Of Christmas” features original lyrics crafted by the renowned songwriting duo Jimmy Van Heusen and Sammy Cahn. This rendition is particularly special as Sinatra shares the microphone with his children, Nancy and Frank Jr., creating a warm family atmosphere. “The Bells Of Christmas” appeared on the 1968 Reprise album The Sinatra Family Wish You A Merry Christmas, adding a personal touch to the holiday collection.
16: Silent Night
This profoundly moving Austrian carol, composed in 1818 by Franz Gruber and Joseph Mohr, has become a staple of Christmas celebrations worldwide. While Bing Crosby’s 1935 recording propelled “Silent Night” into the US Top 10, Sinatra’s version, initially recorded as a Christmas single in 1945, offers its own unique charm. Later included on A Jolly Christmas From Frank Sinatra, Sinatra’s “Silent Night” is characterized by its gentle reverence and vocal sincerity, capturing the song’s peaceful spirit.
15: An Old Fashioned Christmas
In 1960, a pivotal moment in his career, Frank Sinatra departed Capitol Records to establish his own label, Reprise Records. “An Old Fashioned Christmas,” a wistful and nostalgic tune penned by Sammy Cahn and Jimmy Van Heusen, hails from Sinatra’s inaugural Yuletide album under the Reprise banner, the collaborative 12 Songs Of Christmas. Sinatra’s tender delivery and the song’s sentimental lyrics evoke a longing for Christmases past, filled with traditional warmth and charm.
14: The Christmas Waltz
Accompanied by the delightful harmonies of The Ralph Brewster Singers, reminiscent of sugar plum fairies dancing in the snow, Sinatra delivers a truly endearing performance of “The Christmas Waltz.” This often-overlooked gem comes from the creative minds of Jule Styne and Sammy Cahn, two masters of songwriting. Arranged and conducted by Sinatra’s long-time musical partner Nelson Riddle, “The Christmas Waltz” graced Ol’ Blue Eyes’ second Christmas album, A Jolly Christmas From Frank Sinatra. Sinatra revisited this enchanting waltz on 1968’s The Sinatra Family Wish You A Merry Christmas, this time featuring The Jimmy Joyce Singers And Orchestra, proving its enduring appeal.
13: Whatever Happened To Christmas
Penned by the then-rising young songwriter Jimmy Webb, affectionately referred to by Sinatra as “that kid, Jimmy Webb,” “Whatever Happened To Christmas” showcases Sinatra embracing a more contemporary Christmas song. The arrangement, shimmering with a celestial choir and orchestrated by Don Costa, who frequently collaborated with Sinatra in the 1970s, provides a glittering backdrop to Sinatra’s thoughtful rendition. The song explores a sense of modern Christmas losing some of its traditional magic, a sentiment that resonates even today.
12: Christmas Memories
Bathed in lush strings and a quintessential Christmas choir, “Christmas Memories” was released as a non-album single in 1975. Written by the accomplished husband-and-wife songwriting team of Alan and Marilyn Bergman, and arranged and produced by Don Costa, this song encapsulates the bittersweet nostalgia often associated with holiday memories. Sinatra’s emotive performance perfectly conveys the warmth and poignancy of cherished Christmas moments, making it a touching addition to his holiday repertoire.
11: The Little Drummer Boy
“The Little Drummer Boy,” written in 1941 by Katherine Kennicott Davis, gained widespread popularity in the 1950s through recordings by The Trapp Family Singers and The Harry Simeone Chorale. Sinatra’s version, recorded with Fred Waring & His Pennsylvanians – who had previously appeared on his 1964 album America, I Hear You Singing – creates an ethereally atmospheric rendition of this classic tune. Featured on 12 Songs Of Christmas, released in 1964, Sinatra’s “The Little Drummer Boy” is both reverent and captivating, highlighting the song’s simple yet powerful story.
10: White Christmas
This timeless Irving Berlin classic was recorded by Sinatra in 1944, accompanied by an orchestra, choir (The Bobby Tucker Singers), and arranged by Alex Stordahl. Sinatra’s initial recording of “White Christmas” reached No. 7 on the US pop charts and continued to chart in subsequent Christmas seasons, cementing its place as a holiday staple. He later re-recorded the song for Capitol Records with Nelson Riddle and famously duetted with Bing Crosby on the 1957 TV special Happy Holidays With Bing And Frank, further solidifying the song’s iconic status and Sinatra’s association with it.
9: Winter Wonderland
Sinatra’s rendition of “Winter Wonderland” wasn’t initially intended for public release. Recorded for a radio broadcast in 1949, it remained largely unheard until 1994, when it was included on an expanded CD reissue of Christmas Songs By Frank Sinatra. This previously hidden gem features a brief spoken introduction by Sinatra, adding a personal touch. His vibrant and engaging delivery breathes life into this lighthearted and cheerful tune, demonstrating his ability to infuse even the most whimsical material with genuine heart and commitment.
8: Mistletoe And Holly
Opening with playful pizzicato strings, “Mistletoe And Holly” is a quintessential, upbeat Christmas song that carries a special significance as it was co-written by Sinatra himself, along with Dok Stanford and Hank Sanicola. Featuring Gordon Jenkins’ impeccably crafted arrangement and the sweetly harmonized vocals of The Ralph Brewster Singers, it was recorded in July 1957 and released as a single by Capitol Records later that same year. “Mistletoe And Holly” perfectly captures the joyous and romantic spirit of Christmas.
7: I’ll Be Home For Christmas
A solitary, resonant bell toll begins Sinatra’s slow and somewhat melancholic interpretation of “I’ll Be Home For Christmas.” Written by Kim Gannon and Walter Kent, the song was created to bring attention to the soldiers stationed overseas during the holiday season, longing to be home. While Bing Crosby first popularized “I’ll Be Home For Christmas” in 1943, Sinatra’s version, with its sensitive and poignant delivery, makes it distinctly his own. His performance beautifully balances the song’s inherent sadness with an underlying sense of hope, resonating deeply with listeners.
6: I’ve Got My Love To Keep Me Warm
Although Irving Berlin’s “I’ve Got My Love To Keep Me Warm” doesn’t explicitly mention Christmas, its December setting and lyrical references to snow firmly place it within the wintery, Yuletide ambiance. A lively and swinging tune, Sinatra recorded it as the closing track of his first Reprise album, Ring-A-Ding Ding!, in 1961, with an arrangement by Johnny Mandel. Its upbeat tempo and themes of warmth and love make it a perfect, if subtly Christmas-themed, addition to holiday playlists. Notably, it also opens the 2004 Frank Sinatra Christmas Collection, highlighting its festive spirit.
5: Santa Claus Is Coming To Town
Sinatra infused J. Fred Coots and Haven Gillespie’s immensely popular 1934 Christmas hit, “Santa Claus Is Coming To Town,” with a vibrant big band swing makeover. His energetic single version, arranged by Axel Stordahl, gives the classic tune a fresh and dynamic feel. Interestingly, this spirited recording session took place on December 28, 1947, just days after Christmas itself. Sinatra revisited the song a decade later, performing a swing-infused version on his TV special with Bing Crosby, further cementing its status as a Sinatra Christmas swing classic.
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 exuberant rendition of “Let It Snow! Let It Snow! Let It Snow!,” a Sammy Cahn-Jule Styne gem. Ironically, the song was written in July 1945 during a Los Angeles heatwave. Sinatra recorded it five years later, releasing it as a Christmas single even though the lyrics never explicitly mention “Christmas.” The warm background vocals, provided by The Swanson Quartet, enhance the song’s cozy winter atmosphere. “Let It Snow! Let It Snow! Let It Snow!” became a global hit, charting worldwide and achieving its highest position in Hungary, demonstrating its universal appeal as a winter holiday anthem.
3: Jingle Bells
This cheerful Yuletide classic, penned by New England songwriter James Pierpont, was already a century old when Sinatra recorded his definitive version as the opening track of 1957’s A Jolly Christmas From Frank Sinatra. Skillfully arranged by Gordon Jenkins for the first of several Sinatra sessions, this rendition of “Jingle Bells” opens with jazzy, close-harmony vocals from The Ralph Brewster Singers, set against a jaunty, lightly swinging rhythm. Sinatra engages in playful call-and-response with the background singers, adding to the song’s festive and lighthearted charm.
2: The Christmas Song (Merry Christmas To You)
Co-written by singer Mel Tormé in 1945, “The Christmas Song” became a signature hit for Nat King Cole in 1946 and has since been widely covered. Sinatra’s exquisitely understated 1957 recording of “The Christmas Song” is particularly noteworthy. Arranger Gordon Jenkins cleverly incorporates a quote from “Jingle Bells,” played by pizzicato strings, adding a subtle festive touch. The Ralph Brewster Singers provide soft, warm background vocals, creating a truly magical and intimate Christmas atmosphere.
1: Have Yourself A Merry Little Christmas
Topping our list of the best Frank Sinatra Christmas songs is the timeless classic, “Have Yourself A Merry Little Christmas,” written by Hugh Martin and Ralph Blane. This beloved evergreen was first immortalized by Judy Garland in the movie Meet Me In St Louis. Sinatra initially covered it in 1948, delivering a resonant, Bing Crosby-esque crooning performance. However, in 1957, he recorded what is widely considered his definitive version. Gentle, shimmering strings and a subtle choir provide delicate accompaniment, allowing Sinatra’s heartfelt vocals to shine. This version of “Have Yourself A Merry Little Christmas” is the quintessential Sinatra Christmas song, capturing both the wistful and hopeful spirit of the season, and solidifying its place at the pinnacle of holiday music.
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