Frank Sinatra

Like a number of Christmas records from the kings of croon, including singers as deft as Nat King Cole and Johnny Mathis, Frank Sinatra's holiday offerings could be disappointingly stiff and lifeless. Certainly, his reputation precedes him, and I'll grant that Sinatra could turn the Yonkers phone book into sheer aural poetry. It's also true that Sinatra produced an estimable body of Christmas music during his long career for a succession of labels, including Columbia, Capitol, and Reprise. And, those recordings are considered iconic by most Sinatra fans and Christmas buffs.

So, let's take a look at Frank Sinatra's most iconic holiday album, A Jolly Christmas From Frank Sinatra, a 1957 Capitol release with Gordon Jenkins arranging and conducting. It was Sinatra's first formal Christmas album - where he went into the studio to record a complete suite of holiday songs. And, it was cut at the absolute height of Sinatra's powers - right after his masterpiece, A Swingin' Affair, as a matter of fact. We have a right to expect more! If Sinatra had applied his inimitable, world-weary bravado to this seasonal subject matter, we would have had one for the ages. Instead, he sits on his haunches like the frightened, former altar boy he probably was, and we end up with merely an impeccably sung canon of carols.

Easily the best thing on A Jolly Christmas is the debut recording of "Mistletoe And Holly," a song Sinatra helped write - something he rarely did. It's a clever, uptempo song that brings Frank to life. Whether it's his extra skin in the game or the bacchanalian lyrics, the song stands out like a sore thumb amidst the reverent carols and tender ballads that make up most of the album. Elsewhere, it almost goes without saying that Sinatra sings songs like "Have Yourself A Merry Little Christmas" very, very well. But, it ain't got that swing...

This Song of Mine in Three-Quarter Time

Another highlight of Jolly Christmas is Jules Styne and Sammy Cahn's immortal "The Christmas Waltz," but it doesn't really count. That's because Sinatra waxed an even better version of the song back in 1954 as a non-LP Capitol single - its debut recording. The winsome song (and Nelson Riddle's lush production) allowed Frank to take the Christ out of Christmas - and inject some romance. It's no "Night & Day" or "You Make Me Feel So Young," but it's a damn sight better than Sinatra's stiff rendering of songs like "The First Noël" or "Adeste Fideles."

In 1963, Capitol reissued Jolly Christmas as The Sinatra Christmas Album with new, rather boring cover art. Oddly, that was the format they chose when they first reissued the album on compact disc in 1987. Happily, however, they tacked on both sides of the 1954 single as bonus tracks. In 1990, Capitol restored the equally iconic Jolly Christmas cover art (though sometimes with dramatic alterations) when they began a lengthy string of CD reissues, while retaining the bonus tracks on most iterations. The 1999 version was newly remastered, and those are the masters they used for the 2007 edition to commemorate the album's 50th anniversary, except they appended another bonus track (a Christmas Seals message from Frank). And then, that's the version Capitol made available for download and streaming. Since then, the nearly annual parade of reissues has continued, including some colorful editions on resurgent vinyl.

Finally, it's worth noting that A Jolly Christmas From Frank Sinatra is a monaural recording. It was recorded just as stereo was becoming common and, in fact, Sinatra's first stereo recording, Where Are You, was released earlier in 1957. But, apparently, multi-track masters for Jolly Christmas do not exist. If you see copies that claim to be "stereo" or "duophonic," that is fake, reprocessed stereo.

The Boy Singer

Obviously, however, I started in the middle of the story. Frank Sinatra was a middle-aged man by the time he recorded A Jolly Christmas in 1957, and he'd already had quite a career. He got his big break in 1939 as a "boy singer" for the big bands of Harry James and Tommy Dorsey, recording with them for Columbia and RCA Victor, respectively. He wouldn't record any Christmas music during those formative years, but that would change after he signed to Columbia as a solo artist in 1943.

Usually working with Axel Stordahl, an arranger and conductor he poached from Tommy Dorsey, Frank Sinatra recorded a sizable series of Christmas sides for Columbia between 1944 and 1950. By 1944, Sinatra was one of the most popular singers in the world, particularly among "bobbysoxers" whose boyfriends were serving Uncle Sam in World War II. Unsurprisingly, his first holiday recording - a cover of rival Bing Crosby's "White Christmas" - was a major hit, reaching #7 on the pop charts in 1944 and doing even better each of the next two years. But, it adds little to Bing's storied interpretation, and Sinatra's Columbia output suffers from the same malady as his Capitol recordings, consisting mostly of solemn readings of standard Christmas repertoire.

Still, compare the version of "White Christmas" that Sinatra recorded for Columbia in 1944 to the one he recorded for Capitol in 1954 as the b-side of "The Christmas Waltz." Ten years on, he's a much better singer. His voice has been burnished by time and adversity, and his interpretive skills have grown immensely. Guess which one I like better?

So, for me, just three Columbia tracks stand out. Stordahl gives "Santa Claus Is Coming To Town" (1948) and "Let It Snow! Let It Snow! Let It Snow!" (1950) bright, brassy, uptempo arrangements that really kick Sinatra into high gear. Both are great fun, especially "Let It Snow," which features lively vocal interplay with the otherwise obscure B. Swanson Quartet. The third song is a ballad, but it's the sort of deeply romantic song that made Frank Sinatra the biggest teen idol since Rudolph Valentino. Written to order by veteran tunesmiths Irving Gordon and Lester Lee, "Christmas Dreaming (A Little Early This Year)" became a Top 30 pop hit in 1957. It's no masterpiece, but you can almost hear Frank's feverish fans squirming in their seats.

The Voice

In 1948, Columbia cobbled together four previously released singles and four tracks recorded in late 1947 to create Frank's first Christmas album, Christmas Songs By Sinatra. It began life as a 78-rpm album, reissued the following year as a 10-inch LP with new cover art. In 1955, the same material was reissued as a 6-song, 10-inch EP, Christmas With Sinatra (part of Columbia's "House Party" series), and in 1957, it was expanded into a 10-song, 12-inch LP Christmas Dreaming. The Columbia recordings reached their apotheosis in 1994 as a 14-track CD modeled on the original 1948 album. In that format, Christmas Songs By Sinatra collects nearly all the Christmas sides Frank cut for the label - though, to my chagrin, several are presented as alternate takes.

Given the media - compact disc and, later, digital downloads and streaming - Columbia could have easily given us both the alternate take and the official master of those tracks - but who's counting? Generally speaking, the alternate takes are nearly indistinguishable from the official masters, but if you're interested, the Sinatra Discography says the official masters previously appeared on the CD reissue of Christmas Dreaming (1987) and the 12-disc boxed set, The Columbia Years 1943-1952: The Complete Recordings (1993), both of which can now be downloaded or streamed. Finally, it's also worth noting that Sinatra would record no less than seven of the Columbia sides anew after he disembarked to Capitol - all of them traditional carols and Christmas standards.

During his halcyon days at Columbia, Sinatra had yet to find the cool, worldly muse that would inspire his greatest work - but his soaring, youthful voice was a wonder to behold! By the end of his tenure at the label, however, Frank Sinatra's career was in shambles, and he was a very nearly broken man - but that's another story. Instead, Sinatra jumped to a hot, young label, Capitol Records, and flowered into an interpretive genius during the 1950's, cementing his status as one of the greatest voices of the 20th century - A Jolly Christmas, notwithstanding.

The Chairman Of The Board

Capitol Records had been founded in 1948 by songwriter Johnny Mercer as an artist-friendly company, and Frank Sinatra's music flourished during his time with the label. His albums in the 1950's, including Songs For Young Lovers (1954), In The Wee Small Hours (1955), Songs for Swingin' Lovers! (1956), and Come Fly With Me (1958), are the ones upon which his vaunted reputation is based. But, by the start of the 1960's, his relationship with Capitol had soured - Sinatra was a famously volatile personality - and he started his own label, Reprise Records.

Frank Sinatra would record for his own label for the next 20 years, though he sold a majority share to Warner Brothers in 1963. During that time, he produced two major holiday albums, 12 Songs Of Christmas (1964), with Bing Crosby and Fred Waring's Pennsylvanians, and The Sinatra Family Wish You A Merry Christmas (1969), with his children Nancy, Tina, and Frank Jr. Though much beloved by the baby boomers who grew up with it, 12 Songs Of Christmas is a rather stiff, formal affair mixing traditional carols with mostly recycled modern pop songs. Frank and Bing's "Go Tell It On The Mountain" (an old spiritual) and "We Wish You The Merriest" (a 1961 Les Brown composition) stand out thanks to their spirited arrangements. Of Sinatra's solo numbers, "An Old Fashioned Christmas" (a new song written by Sammy Cahn and Jimmy Van Heusen) is the keeper, giving Sinatra the chance to stretch out while singing Cahn's clever, pointedly nostalgic lyrics. An interesting footnote: Sinatra, Crosby, and Waring had collaborated on a patriotic album, America, I Hear You Singing, earlier the same year, appealing to much the same middle American demographic.

I should point out that, despite its enduring popularity, 12 Songs Of Christmas has never been formally reissued on CD. A total of six tracks showed up on Sinatra's Christmas Collection (see below) and Bing's The Crosby Christmas Sessions, and the whole thing was appended to a special 2009 "Christmas Edition" of the 2008 Sinatra retrospective, Nothing But The Best.

Some Children See Him

The Sinatra Family Wish You A Merry Christmas is a more ambitious effort, even as it leaned heavily towards the "easy listening" market that emerged in response to rock 'n' roll's takeover of pop radio. All the kids get a spotlight number, and the album includes new compositions by emerging songwriters Chip Taylor ("It's Such A Lonely Time of Year," sung by Nancy) and Jimmy Webb ("Whatever Happened To Christmas," sung by Frank, Sr.), plus a new number by veterans Sammy Cahn and Jimmy Van Heusen ("I Wouldn't Trade Christmas," sung by the whole family). Perhaps the highlight, however, is a humorous rewrite of "The Twelve Days Of Christmas" sung by the kids. Their "loving dad" is getting an abundance of ties, cuff links, scarves, books, golf clubs, and more, prompting Frank to exclaim, "Oy vey!"

Without getting too deep in the weeds, I should mention that there's surprising disagreement about when Wish You Merry Christmas was released. Sinatra scholars agree it was recorded in 1968 - July 25th and August 12th, to be precise. But, a lot of sources give 1968 as the release date, while a lot of others say 1969. In truth, only a single was released in 1968: Frank's "Whatever Happened To Christmas?" b/w the Family's "I Wouldn't Trade Christmas," which reached #7 on Billboard's Christmas chart in December. Confusingly, the single explicitly states that it is taken from "The Sinatra Family Wish You A Merry Christmas," which wouldn't be released until the following year - a fact confirmed in the December 13, 1969, issue of Billboard, which describes Wish You Merry Christmas as a new release.

Anyway, beyond those two Reprise albums, Frank Sinatra generated just a few other holiday tracks during the last four decades of his life. These include a swinging "I've Got My Love To Keep Me Warm" from his album Ring-A-Ding Ding! (1961) and an intimate "Have Yourself A Merry Little Christmas," the third and best time Sinatra assayed the 1944 Judy Garland classic. That latter song is from a Reprise album that, sadly, has never been reissued in the digital age, Frank Sinatra And His Friends Want You To... Have Yourself A Merry Little Christmas (1963). As you might guess, it's a collection of Frank's friends and label mates - including Keely Smith, Les Baxter, Billy May, Nelson Riddle, Joe Stafford, Dean Martin, and Sammy Davis Jr. - singing traditional Christmas songs. Nothing earth-shaking, but still...

Oh, By Gosh, By Golly

In 1975, Frank Sinatra recorded a brand new holiday single featuring two brand new songs. The a-side, "A Baby Just Like You," was written by Frank's unlikely new friend, folk/pop superstar, John Denver, and his frequent collaborator, lyricist Joe Henry. Reportedly, they wrote it upon request to mark the birth of Sinatra's first grandchild, Nancy's daughter Angela (who is name checked by Frank in the final verse). The b-side, "Christmas Memories," was composed by the noted songwriting team of Alan Bergman and Marilyn Bergman ("The Way We Were") with longtime Sinatra associate Don Costa. The single went nowhere, but Denver went on to record his own version of the a-side (name checking his own son, Zachary), while the b-side became a minor modern standard recorded by Barbra Streisand, Rosemary Clooney, and She & Him, among others.

Frank Sinatra's Reprise holiday recordings have been surveyed a couple of times, starting with The Sinatra Christmas Album (1994), which was later expanded and remastered as The Christmas Collection (2004). In its latter configuration, the album collects tracks from 12 Songs Of Christmas and The Sinatra Family Wish You Merry Christmas, plus all the loose ends mentioned above. It also features three rare tracks from the 1957 TV special, Happy Holidays with Bing and Frank, and a 1991 recording of "Silent Night" - Sinatra's last Christmas recording - made for a benefit, The Christmas Album... A Gift Of Hope.

This was Sinatra's fourth official version of the well-worn carol, and it originally featured Frank's solo vocal, accompanied only by Frank Jr. on piano. For The Christmas Collection - released six years after Sinatra death in 1998 - longtime Sinatra insider Johnny Mandel arranged new orchestrations, which Junior conducted using an orchestra staffed with several longtime Sinatra sidemen. I'm usually not a fan of such revisionism, but it works beautifully, and it's a fitting tribute to the man who changed the face of American music.

Start Speading The News

So, that's 50 years of Frank Sinatra's Christmas music spanning four albums, plus assorted singles and tracks. That's a lot. Moreover, there's a shit-ton of budget-oriented, after-market Sinatra collections cluttering up the marketplace - a situation grown far worse since the advent of digital downloads and streaming. So, where do you start? For almost everybody, Christmas Songs By Sinatra, A Jolly Christmas, and The Christmas Collection cover all the bases - Columbia, Capitol, and Reprise, respectively. Anything else is a pretty deep dive.

If that's still too much, I recommend Ultimate Christmas (2017), a 20-track collection of both Capitol and Reprise recordings available in all formats, including some colorful vinyl editions. Still too much? Check out Christmas With The Rat Pack (2002), an oft-reissued collection of highlights from Frank and his storied crew, Dean Martin and Sammy Davis Jr. [top of page]