I have written before of my discovery of Sinatra and his ilk in the late fall of 1996 and I have often shared of my learning about vocal jazz through Swingers and Harry Connick, Jr. in these pages. I won’t go over the same ground again but I will say that because these epiphanies happened at the outset of winter that year, I anticipated the coming Christmas and my perusal of the swingin’ sounds of the season. Harry Connick came through huge when I unwrapped his excellent When My Heart Finds Christmas and this made me anticipate the yuletide offerings of Francis Albert all the more. But much to my surprise, when it comes to Christmas music, the greatest swinger of all time…doesn’t.

My first purchase of the Christmas music of Frank Sinatra was a truncated version on cassette of his 1957 album with Gordon Jenkins A Jolly Christmas from Frank Sinatra. I was totally unprepared for what I heard. But before we get there, let’s start at the beginning. Sinatra recorded Christmas music at all three of his major record labels, Columbia, Capitol and Reprise. He was quick out of the gate with this genre, having recorded his first Christmas song – the venerable “White Christmas” – on November 14, 1944. Over the course of the next few years, Frank would issue singles as Christmastime offerings to his fans until Columbia finally compiled all of these tracks onto an album.

Christmas Songs by Sinatra (1948) — Frank’s original Christmas album came early in his career. Not only was “White Christmas” recorded at just his sixth session with Columbia but Christmas Songs was only his third album release. By 1948, Bing Crosby had already made it de rigueur for popular artists to release records of Christmas music and Crosby’s immortal Merry Christmas LP had been a huge seller and was fast becoming the perennial chestnut it remains today. Frank and Columbia followed suit with this set that was initially issued as an album of 78 RPM records and then as a 10″ LP. There’s eight tracks here and Frank shines on the contemporary fare as well as the carols. It is interesting to note that, in terms of swingin’, FS offers the venerable “Jingle Bells” and the equally hallowed “Santa Claus is Comin’ to Town”. While Frank’s versions are certainly jaunty, they sound sterile when compared to Crosby’s recent recordings with the Andrews Sisters of these same two songs. Crosby’s versions contain more pure swing – sheer rapturous energy, bounce and fire – than almost any other recordings – Christmas or otherwise – from this golden era laden with swinging music.

In 1994, Columbia reissued this record on compact disc, adding the delightful “Christmas Dreaming (a Little Early This Year)” and “Let It Snow! Let It Snow! Let It Snow!” that Frank recorded around the same time. Oddly, among the eight original tracks, three are offered on this CD as they were but the other five are presented as alternate takes as opposed to the original masters from the 1948 album. As bonus tracks, we get to hear Frank sing from rehearsals for his radio program and from one of the many V Discs that he recorded to be shipped overseas during the war. There is an introduction from the Chief of Special Services and then Frank gives the troops a little piece of home with some carols and a nice “Winter Wonderland”. But even here, he avoids the light-hearted and instead favours the reverence of “The Lord’s Prayer” and “Ava Maria”. Be aware, though. As I’ve previously warned in the Frank episode of Christmas Caveats, these same songs have been re-released many different times adorned with a lot of different cover art. Christmas Songs by Sinatra is required for you to own. Mostly because without this you can’t complete the relatively simple task of owning all his Christmas music and also because it’s a pleasant record if unremarkable.

A Jolly Christmas from Frank Sinatra (1957) — This is an absolutely sumptuous, erudite record that Francis made with the sumptuous and erudite Gordon Jenkins. Frank having made this LP with the orchestra and chorus of Jenkins should have been a tip-off that this was not going to be a ring a-ding-ding Yuletide. But when I was still apprenticing in the world of Sinatra I knew little about his catalogue and certainly knew nothing about his favoured arrangers and their individual styles. I didn’t know that Frank altered history with the urbane, swingin’ records he made with Nelson Riddle or that Sinatra’s albums with Billy May often featured big, fat brass or that he entered the soft pop/adult contemporary arena under the baton of Don Costa. And I certainly didn’t know that the forte of Gordon Jenkins was lush, sweeping strings that spoke the language of both the heights of reverie and the depths of despair.

So, here’s me, dumb. I listen to A Jolly Christmas and I’m disappointed?! I know, right? As I often say, expectations have ruined many a great film (or record) and, after a buoyant start, I wasn’t prepared for the reverent approach Sinatra takes on this record. But once I recovered, I found a deeply penetrating work. The “Jingle Bells” that starts the program off is delightful and features Jenkins’ female singers making like hepcats or kittens; “I love those J-I-N-G-L-E bells…” It’s a great, mid-tempo take on this nugget. On a personal note, back in the day, I made Christmas mixed tapes that were all-world. You’ve probably heard of them. I would often sneak clips from Christmas-themed movies into the tapes somewhere and one collection started with a clip from Diner that had a television announcer intoning “This is WBAL Channel 11 in Baltimore wishing all our viewers a Merry Christmas and a Happy New Year” and right after this came Frank’s “Jingle Bells”. Legend.

After “Jingle Bells”, the rest of the first side “is devoted to popular Yuletide favorites of recent origin” including the charming “Mistletoe and Holly”, a song Frank is credited as having co-written. “The Christmas Waltz” is another song that “belongs” to Frank as it was written for him by Sammy Cahn and Jule Styne. This delightful song, introduced by Frank, has become a Christmas standard and has been recorded countless times (dig Nancy Wilson’s). I’ve actually gotten into the habit over the years of answering “And to you, Francis” when Frank says “Merry Christmas” at the end of “The Christmas Waltz”. Sometimes I get a bit emotional. I dunno…it just seems so nice.

“On Side Two, Sinatra sings the traditional carols”. Here we consider an artist from another time, who’s memories stretch back to an even more distant past. Here is an artist who, in a youth that contained at least some measure of Roman Catholicism, recalls beloved Christmas songs that sprang from a place of devotion and faith. This, really, is where the money is. Sinatra’s pitch-perfect renderings of these carols – “O Little Town of Bethlehem” and “Silent Night” among many others we all know – bring to the listener the pure depth of feeling that comes with the season. Whether your focus is the birth of Christ or not, hearing Frank sing these songs goes straight to your spirit. Carols are ancient treasures, beloved by generations and hearing them at Christmas – especially in the perfect setting that Sinatra, Jenkins and the Ralph Brewster Singers provide – is one of the joys of the season. When the room is warm, lights are low, loved ones are near and you are reflecting on your blessings and cherishing a feeling of peace, this side of this record is what you want playing. Finally, consider that the cassette version I started with only contained 9 songs, omitting the jaunty numbers; so the “Jolly” was even more confusing to me. This record is total class.

12 Songs of Christmas (1964) and The Sinatra Family Wish You a Merry Christmas (1968) — Frank Sinatra never again entered the studio to record a solo Christmas record but he did make more seasonal music. Sinatra made two curious albums with Papa Bing and Fred Waring and The Pennsylvanians; both of them were the last albums I had to find and buy to complete my Sinatra Album Collection. America, I Hear You Singing (also ’64) has little to recommend it, really. The patriotic album was a tribute to recently slain president John F. Kennedy and is perhaps too ephemeral to be enjoyed today. It’s available on iTunes. 12 Songs of Christmas is a fine record that I had to buy on vinyl from eBay – something I’ve only done once before when I bought Dean Martin’s Once in a While album to complete my Dino collection.

The highlight of the record and, indeed, one of the finest Christmas songs ever recorded is Frank’s “An Old-Fashioned Christmas”. This Cahn/Van Heusen track is a heartfelt paean to longing and nostalgia. Interesting that we today may long for an old-fashioned Christmas like the ones they had, say, in 1964. But here is Frank – in ’64 – longing for a simpler time, as well. This song could be a film. Through Sammy Cahn’s lyrics, Frank laments that he is too much of a swinger. He has been too long in the “steel and chrome” jungle of Manhattan and he’s realizing that – in successfully conquering life – he has strayed from his roots, from what is pure. His mind harkens back and he sees his mother cooking in the kitchen and he longs to return to sit placidly by the fireplace because his “heart remembers smouldering embers warmly aglow”. He has enjoyed much personal and professional acclaim but he would gladly trade the skyline he obviously owns “for one old-fashioned Christmas back home”. It’s a touching, graceful song beautifully rendered. Additionally, Frank duets with Bing with fine results on “Go Tell It on the Mountain” and Les Brown’s jubilant “We Wish You the Merriest”.

The Sinatra Family record is intriguing. Again, Frank doesn’t do all the work and that results in perhaps an uneven record but a charming one. Cahn and Van Heusen are on hand again and they provide the humourous opener “I Wouldn’t Trade Christmas”. By far – by miles – the highlight of the album is Nancy’s devastating “It’s Such a Lonely Time of Year”. The song was written by Chip Taylor, author of “Wild Thing” and “Angel of the Morning” and I was today years old when I learned that Taylor was born James Voight and he is Jon Voight’s brother! “Lonely Time” is the saddest Christmas song you’ll ever want to hear but Nancy does well and the song is of a very high quality. If nothing else, it will make you cherish your significant other all the more. Another Christmas gem that Sinatra introduced is Jimmy Webb’s “Whatever Happened to Christmas?” and Frank revisits “The Christmas Waltz”. The whole family joins forces to present a unique “The Twelve Days of Christmas”.

If you pick up 1994’s The Sinatra Christmas Album on Reprise you’ll get Frank’s tunes from the Crosby/Waring album and from the Family album as well as a single FS put out in 1975. “A Baby Just Like You” – written by John Denver – and particularly “Christmas Memories” are two gentle and wonderful additions to Sinatra’s Christmas canon.

You could do worse than to emulate me but don’t make the mistake I made and assign expectations to any of Frank Sinatra’s music. His Christmas recordings are a welcomed part of the season but just don’t expect high energy. Frank has chosen to present the reverent side of Christmas, the wistful, nostalgic side. And this is fitting. The office party aside, Christmastime is not always about aggressive fun or loud excitement. It’s often about exhaling and enjoying a brief, quiet respite from worldly cares. I’ve always said that one of the most poignant things about this glorious time of year is it’s fleeting nature. This in itself makes Christmas special – after all, watch White Christmas in July all you want and you cannot convince me that it feels the same as watching it with family on Christmas Eve. So, the idea that Frank delivers placid, warm, elegant Christmas music makes good sense. And for excellent visual companions, seek out Happy Holidays with Bing and Frank on DVD and The Dean Martin Christmas Show from December 21, 1967 that features Dean’s family and Frank’s family that once could be found on YouTube. The Martin family released the episode to public television in 2021, though, and have removed the video.