Frank Sinatra at Yuletide

How the Chairman of the Board saluted the season in song over the years

Welcome music lovers once again and season's greetings!

Below is my last of three essays this year on the sounds of the season. This time, I reflect a bit on the recordings Frank Sinatra made of Christmas music, beginning in 1944 and ending in 1975. I hope you enjoy it and will share your thoughts on what I have written.

This is the last time I will be in touch this year. It’s been a good year and it's in large part to you all for your support of my work and for letting it enter your inbox every 10 days. There are some who feel that Substack is captive to the major players on this platform and while there may be some truth to this, the power of Substack rests in the many fine writers and attentive readers who have flocked here in the past few years. One of my greatest pleasures in 2024 has been the chance to collaborate with a few of the community of music scribes on Substack: Tim Riley, Brad Kyle, Chris Dalla Riva, Ellen from Endwell and Dan Epstein. More of this in 2025 please! As well, I have deeply enjoyed interacting with many others here about music and can’t imagine any other way that I would connect with many of you. The holidays is, in part, about gratitude and I feel it in abundance. Thank you all!

And so, in closing, I hope that no matter how you choose to mark the holiday season, joy and peace will find you in their full measure and that the New Year will be good to us all!

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There are two pieces of trivia I cherish about A Jolly Christmas from Frank Sinatra, the Chairman’s sole full-length seasonal album. The first comes from a radio piece that playwright and lyricist Murray Horowitz did with critic and poet A.B. Spellman in 2001 for their Basic Jazz Library series that ran on National Public Radio. Horowitz recalled that he had worked with Stan Getz once for a benefit. After the show, Getz left a shopping bag behind. In it was a CD copy of A Jolly Christmas from Frank Sinatra. When Horowitz gave the bag back to Getz, the tenor saxophonist remarked to Horowitz, “you know, this is the greatest Christmas album anybody ever made.”

The second is that the cheerier lyrics often associated now with ‘Have Yourself a Merry Little Christmas’ in which, for example, “through the years, we will all be together” instead of “someday soon, we will all be together,” as Judy Garland sang in Meet Me in St. Louis, are because in 1957, Sinatra asked songwriter Hugh Martin to pen them so that the song would be more in line with the jolly vibe of his planned Christmas LP.

Sinatra had recorded his interpretation of Garland’s version in 1947 and again for his third and final recording of it in 1963. While no singer arguably recorded as many definitive versions of popular songs as Sinatra, I’m not sure I would include any of his goes at ‘Have Yourself a Merry Little Christmas’ on a list of the five to ten great recordings of it. The reference recordings, for me, are Garland and (throwing a curveball here) Connie Francis’ lush version from 1960 as well as Cécile McLorin Salvant’s interpretation from 2014 with the Lincoln Center Jazz Orchestra (here, she sings Martin’s very first attempt at the lyrics, which are the darkest of all). Sinatra, naturally, sings the song with reverence but is seemingly at a remove, reciting them more than living them.

That’s not meant to be a knock against Mr. S—to me, he remains at the top of the pop-singer heap—but just a reflection of what my ears are telling me. Christmas would indeed be gloomier if Sinatra wasn’t part of the seasonal soundtrack but unlike, say, Tony Bennett, Ella Fitzgerald, Nat Cole, Louis Armstrong, Dean Martin, Bing Crosby, Perry Como, Johnny Mathis or other luminaries of the golden days of the pop singer, I would argue we listen to Sinatra at Christmas time for slightly different reasons than the others.

His seasonal recordings roughly break down into four collections: a series of sides from the forties, the bobbysoxer era, A Jolly Christmas from Frank Sinatra appearing in 1957, smack dab in the era when Sinatra was conquering the LP, contributions to three collections on Reprise in the sixties, and finally, singles from 1954 and 1975. It’s a survey of not only Sinatra’s approach to the standards and carols of the season but also illustrates the evolution of his artistry.

By far the most well-known of his early Christmas recordings is ‘Let It Snow! Let It Snow! Let It Snow!’ from November 1950, the cusp of his brief fall from grace. It anticipates the wide-brim snap of the up-tempo finger snappers he would make for Capitol as part of his reinvention into the persona that still sticks as how most perceive Frank Sinatra. A bit of callow youthfullness, though, remains in his vocal, an impression underlined by the vocal chorus, the B. Swanson Quartet, that appears alongside him, bringing to mind both the Pied Pipers and his days as a band singer with Tommy Dorsey. As well, the effort that Sinatra makes to swing and sound carefree is readily apparent. Soon, he would make it seem oh so effortless.

More natural is his 1947 take on ‘Santa Claus is Coming to Town,’ one of a handful of early notable versions of the seasonal standard—Bing Crosby with the Andrews Sisters is the prize recording with Perry Como and especially Johnny Mercer finding the sweet spot too. It’s notable as well as being the only other time that the young Sinatra went up-tempo with Christmas.

His recording of ‘White Christmas’ is earnest and the use of a chorus—here, it’s the Bobby Tucker Singers—is very effective on the repeat of the verse. A slow ‘Jingle Bells’ is kind of daring and ‘Christmas Dreaming (A Little Early This Year)’ is the singer’s first crack at putting his signature on a Christmas song of his own. It hasn’t been entirely forgotten even as it’s fairly wordy and melodically awkward. His next attempt in the following decade would be far more successful.

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Where Sinatra most made his mark in the forties with Christmas music was through the venerable hymns. Here, his vulnerability as a singer—seen by many as the secret to how he quickly leaped ahead of his contemporaries—comes to the fore. These are reverent performances, especially ‘It Came Upon the Midnight Clear’ and ‘O Little Town of Bethlehem.’ It’s worth noting that Bob Dylan’s recording of the latter carol for his Christmas In My Heart is almost an exact homage to Sinatra’s.

Seasonal nostalgia is often contingent on the lighter side of Christmas music, full of sleigh bells and cheer, but it’s also found in abundance, at least in my opinion, in Sinatra’s straight-and-narrow interpretation of the hymns.

He would return to these songs only once more, dedicating the second side of A Jolly Christmas from Frank Sinatra to them (a familiar gambit for Christmas LPs with the opening side dedicated to the secular side of the holidays).

Nineteen fifty-seven was a big year for Sinatra—maybe his best during the years during which he was dedicated to recording LPs, often centred around a concept, of selections primarily from the Great American Songbook (I would ballpark the time period between 1954 and 1967). Three of his finest albums were released that year: the upbeat A Swingin’ Affair with Nelson Riddle, the romantic travelogue of Come Fly With Me (for me, the peak of Sinatra on twelve inch) with Billy May and Where Are You? with Gordon Jenkins who also wrote the charts for A Jolly Christmas from Frank Sinatra.

In a way, that’s hard to believe. Jenkins’ writing for Sinatra was often rapturous and occasionally to excess. Here, it is restrained, often unobtrusive and occasionally quirky.

There are unexpected pauses in the choral parts, noticeable most on ‘The Christmas Song’ and ‘Hark! The Herald Angels Sing’ (another arrangement that Dylan copped). I suspect these were written by Jenkins to go beyond the garden-variety sound of stately performances with the singer adhering to the melody on the page and the choir offering support, often in unison. That’s side two of the album in a nutshell and even as Sinatra’s voice matured, the vulnerability tempered by the incontrovertible fact that he had, as the Harold Arlen and Ted Koehler song went, “the world on a string,” they are worthy recordings.

‘The First Noel,’ which opens the side, has Sinatra singing the opening verse directly and irony free and the aforementioned ‘Hark! The Herald Angels Sing’ has him negotiating the lifts in the melody with impressive control. For a second time, he demonstrates an affinity for ‘It Came Upon the Midnight Clear.’ Above all, they illustrate the earliest lesson I received about Sinatra, care of my father: the diligence he put into enunciation and diction.

You don’t hear much of A Jolly Christmas from Frank Sinatra’s second side on the radio but you do hear a whole bunch of the opening side—a natural outgrowth of the preference for the non-religious songs of the season. The results are varied.

Just as Sinatra never quite connected with ‘Have Yourself a Merry Little Christmas,’ he also never quite grabbed hold of the feeling of anticipation that is the heart of ‘The Christmas Song.’ He does, on the other hand, meaningfully connect with the longing of ‘I’ll Be Home for Christmas.’

The remaining three performances from the album are really the only ones that could be considered jolly. ‘Jingle Bells’ again recaptures the spirit of Sinatra’s start as a band singer. ‘Mistletoe and Holly,’ one of a handful of times that the singer had a hand in writing a song, has Jenkins’ most extroverted chart for the LP—dig those pizzicato strings—and is delightfully tongue-in-cheek. And then there’s ‘The Christmas Waltz.’

Written for the singer by Sammy Cahn and Jule Styne in 1954 and put on a 45 with a tepid re-recording of ‘White Christmas,’ the song is Sinatra’s most well-known contribution to the seasonal canon. The first recording, with a Riddle chart, is light and understated. Jenkins’ chart emphasizes the 1-2-3, 1-2-3 rhythm and also includes a brief choral introduction. Both choices emphasize the consequence of the season as does Sinatra’s performance. The impression here is sweet and sentimental.

Eleven years later, Sinatra recorded ‘The Christmas Waltz’ one last time with Riddle again arranging. The occasion was for the album, The Sinatra Family Wishes You a Merry Christmas, that included contributions by children Nancy, Frank Jr. and Tina. The approach here is rich and rapturous. The waltz time is only implied. It is a transcendent recording.

By 1968, Sinatra’s golden era was setting and in its last years—beginning in roughly 1963—his voice had reached its peak. His tone became richer and darker as if callused by the years. His control was deeply refined and his expressive power as commanding was as it ever would be. The combination of it all meant his vocal performances often approached works of art. That’s how I would characterize his approach to ‘Whatever Happened to Christmas?,’ written by Jimmy Webb, his other solo piece for the family seasonal album. For just one example, hear how he adds a pause on the concluding part of this line: “remember how love was all around / whatever happened to it all?”

Nostalgia is in the air. The sound of a gracefully aging Sinatra reflects the role he had played in so many lives as well as his place as an imagined ideal. I find this recording moving, as a result. ‘An Old Fashioned Christmas,’ recorded four years earlier for a joint project between Sinatra, Bing Crosby and Fred Waring and the Pennsylvanians for Reprise, 12 Songs of Christmas, is similarly poignant.

The jewel of that collection, though, is Sinatra and Crosby duetting on ‘We Wish You the Merriest.’ There is a lot going on in this recording: an orchestra with strings, a move into waltz time on the second bridge plus Waring’s Pennsylvanians but it all doesn’t obviate its good-natured joy. Sinatra and Crosby sound like they are having a ball. But beneath the bravado, there is an emotional wallop from the presence of Crosby. Listen and ponder how they marked the times for so many.

Sinatra’s final contribution to the sounds of the season came in 1975 with a single. The A-side was a song written by John Denver with Joe Henry to commemorate the birth of Nancy Sinatra’s daughter, Angela. ‘A Baby Just Like You’ is beautifully sentimental. The B-side, ‘Christmas Memories,’ written by Alan and Marilyn Bergman with Don Costa who also arranged it, has Sinatra doing what I suspect many of us are doing right now: reflecting on the celebrations of years gone by and seeing how they connect to what is happening this year. It is a low-key recording—one chorus and that’s it—but as always with Sinatra, his ability to communicate at a level beyond almost everyone else turns it into something deeply resonant. It may not be jolly but it sums up how this season can be beautiful.