Let’s face it: Christmas simply wouldn’t be Christmas without the soothing sounds of traditional oldies music echoing through the house. The holiday season and classic American melodies are inextricably intertwined in western culture. In fact, Christmas doesn’t really seem like Christmas until you’ve heard a warm baritone voice singing “Silent Night” or “Have Yourself A Merry Little Christmas,” either on the radio, in a restaurant, a shopping mall, or at home on the stereo. Among the titans of this era, Frank Sinatra stands supreme. Hearing his voice helps to conjure the spirit of the approaching holiday season, and when you hear Ol’ Blue Eyes wrap his voice around “The First Noel,” you know that the holidays are well and truly on their way.
So where does this timeless association between the golden era of American music and Christmas come from? Well, it goes right back to 1948, the year the LP format was introduced by Sinatra’s then record label, Columbia. That was when the 32-year-old man who would come to be known as The Chairman Of The Board released Christmas Songs By Sinatra, the first of many iconic holiday projects, arranged by the redoubtable Axel Stordahl. It contained eight traditional holiday songs, beginning with “White Christmas” (a song he first recorded in 1944 as a single), alongside carols such as “O Little Town Of Bethlehem” – apparently one of Sinatra’s favorites – and culminating with “Santa Claus Is Coming To Town.”
A Jolly Christmas With Frank Sinatra and the Evolution of Holiday Classics
The world would have to wait nine years for another major holiday release, by which time Sinatra had established himself as a master of The Great American Songbook and moved to a new label, Capitol, for whom he would serve up some of the best work of his career. By 1957, the singer was once again in the mood to celebrate and released his second festive LP, A Jolly Christmas With Frank Sinatra. This record found him revisiting some of the songs from his first Yuletide album as well as recording new material in the company of arranger Gordon Jenkins.
What’s striking about that album is the version of “Have Yourself A Merry Little Christmas,” a song written by Ralph Blaine and Hugh Martin, and originally sung by Judy Garland in the 1947 movie Meet Me In St Louis. Evidently, Sinatra felt the original lyrics were too downbeat for his taste.
In 2007, a 93-year-old Hugh Martin recalled that, back in 1957, prior to recording the song for the second time, Sinatra called the lyricist to ask if he would rewrite the “muddle through somehow” line. The songwriter remembered that Sinatra told him: “The name of my album is A Jolly Christmas. Do you think you could jolly up that line for me?”
Martin agreed and made several revisions, the major one being the removal of the line “Until then we’ll have to muddle through somehow,” replacing it with “Hang a shining star upon the highest bough.” The alteration completely lifted the mood of the song, transforming it from a lugubrious meditation into a quietly uplifting song of hope. This masterstroke helped to transform a largely-ignored movie tune into a bona fide standard that a raft of famous American singers have since covered.
The first major television holiday special was also recorded for TV in 1957. Happy Holidays With Bing And Frank was aired on December 20, helping to cement in the public’s mind an indelible association between these legendary figures and the holiday season.
The Reprise Era: “I Wouldn’t Trade Christmas”
Three years later, in 1960, a 45-year-old Sinatra left Capitol to found his own record company, Reprise, and began a new phase of his career. Though he contributed one song to a 1963 compilation LP called Frank Sinatra And His Friends Want You To Have Yourself A Merry Little Christmas – a festive showcase of artists on the Reprise label – it wasn’t until the following year that he recorded his first proper Christmas album for his new company.
12 Songs Of Christmas featured his old sparring partner, the sonorous-voiced Bing Crosby, on two songs, while the backing was provided by popular bandleader Fred Waring and his Pennsylvanians.
Four years on, in 1968, a very different festive extravaganza emerged, courtesy of The Sinatra Family Wish You A Merry Christmas. Though it was recorded in July and August of that year, the arrangements – complete with tinkling sleigh bells – helped to conjure an authentic winter feeling. The album combined traditional Yuletide fare with lesser-known ditties such as Sammy Cahn and Jimmy Van Heusen’s “I Wouldn’t Trade Christmas,” and Jimmy Webb’s “What Happened To Christmas.” With stellar arrangements by Nelson Riddle and Don Costa, heartwarming performances were delivered alongside his children Nancy (whose own career as a singer was blooming spectacularly at this point), Frank Jr., and Tina.
The True Spirit Behind the Voice
Since his passing in 1998, there have been countless compilations dedicated to this seasonal material. The most significant of them is the Frank Sinatra Christmas Collection, which came out in 2004 and cherry-picked key cuts from his Reprise era. What distinguished it from other releases was the inclusion of previously unreleased material, including a duet with Bing Crosby and a rendition of “Silent Night” recorded in 1991 at the age of 75. It marked the final time Ol’ Blue Eyes recorded a Christmas carol.
We know that he liked to record Yuletide songs, but what was his true take on the holidays? According to his daughter, Nancy, her father absolutely loved the holiday season. “Nobody embraced Christmas as he did,” she remembered in an interview. That’s not surprising, given the warmth and sincerity that shines through his many recordings of Yuletide songs.
Christmas, then, wouldn’t be the same without these timeless melodies. For many, oldies music brings the holidays vividly to life, making the tinsel glitter and the snow glisten while warming our hearts with a profound sense of bonhomie and goodwill to all. Aside from being a time of both religious observance and exchanging gifts, Christmas is also a time of celebration – and no one could celebrate quite like the icons of American music.
It’s not outrageous to contend that these classic recordings provide the ultimate soundtrack for the season. They are to the holidays what snow is to winter: an essential component of the whole experience. The songs provide an essential backdrop that is mellow and reflective, yet also bright and mirthful, conjuring up the “happy golden days of yore.” They remain at the very top of the holiday tree for generations to come. Let us embrace these timeless sounds and explore more of these everlasting melodies to make every holiday season unforgettable.

