Christmas Caveats: Dean Martin

For many of us who love Vintage Leisure, one of the most significant things we appreciate about the entertainment of the past is the feeling of warmth and sincerity we get from it. The lack of cynicism. I have noticed something about Dean Martin. No doubt, Dino looms large over the media of mid-century; we all love his records, his films, his television work. But – and I don’t feel that this is an indictment of Dean – it seems to have never really been his thing to be overly heartfelt or serious. He was not what you’d call a comedian, but much of his appeal springs from how light he always kept it.

This is particularly noticeable in his Christmas music. It is a topic for another article but Dino’s Yuletide offerings are mostly centered on “making spirits bright”. Our concern today is looking at the many iterations of Dean Martin’s two Christmas records. As we’ve seen in other episodes of Christmas Caveats, an artist may have indulged in songs of the season maybe only once or twice in his or her career but their record companies didn’t let that stop them from continually mining a singer’s Christmas music. Dean, by the way, had been an early hero of Elvis Presley‘s and Dino and EP have this in common; they each recorded Christmas LPs twice in their careers. And both men did so at different points in their careers, the second for both coming by the time they had modified their sound. Dean did so at both of his major labels. Another similarity lies in the plethora of releases that have come from the Christmas music of these guys and the appearance of virtual duets. Both men have Martina McBride in common, too! Let’s get started. I don’t want you to buy the wrong thing.

A Winter Romance

Capitol, 1959

8 songs, 39 different versions 1959 – 2015, 4 different titles, 7 different covers

© Capitol Records

First of all, I say this record has 8 songs on it. Note that Dean’s record is called A Winter Romance; neither the title nor the cover art denotes Christmas. I count four songs on the album that are neither Christmas songs nor expressly winter-themed and could easily appear on any other regular type of album.

Capitol did with Dino the same thing they did with his pallie, Francis and at the same time for the same reason – Martin left the label for Reprise Records. Capitol took Dean’s Christmas record and re-issued it 12 different times in three different countries between 1962 and 1967. Perhaps to combat his Christmas release on Reprise of 1966, Capitol attempted to bamboozle the public by re-releasing A Winter Romance with technically three different titles and two different covers. The first cover they used is not half-bad and I see they’ve utilized the exact same back cover which helps to cement my case that changing just the front cover art was key to getting people to think they did not own this music.

Interesting to note that Capitol not only hoped to move what looked like a “fresh” album off the shelves that Christmas but they also hoped to do it by offering less songs than on the original LP. Inexplicably, the two tracks they left off are among the stalwarts of the season – “Rudolph, the Red-Nosed Reindeer” and “White Christmas”. Baffling. Those two tracks were restored in ’65 for Holiday Cheer but “A Winter Romance” was left off; after all, this version did not bear that name.

In 1998, the album was again repackaged for international sales with some very poor, generic cover art. What is also mind-boggling is the six tracks that were added. Dean singing Christmas on the radio? A Yuletide B side? Nope – “How Do You Speak to an Angel?”, “Two Sleepy People” and even “On an Evening in Roma”! Bizarre. The same crazy line-up was issued elsewhere in intervening years with various covers. Collector’s Choice Music finally restored things to normalcy in 2005 with a reissue of the proper album accurately sequenced and with the original charming cover art. They threw in four non-Christmas singles as bonus tracks.

The Dean Martin Christmas Album

Reprise Records, 1966

9 songs, 37 different versions 1966-2020, 1 title, 2 covers

© Reprise Records

Remarkably, this album has not been much fooled with over the years. It was issued on LP, 8-Track tape, cassette and reel-to-reel in the US and on vinyl worldwide in ’66. The record was released only sparingly through the years and then in 2017 it saw a proper CD release in North America. In a nice touch, Legacy put it out on red vinyl in 2020. Oddly, in 2008, the record had seen a release as A Very Cool Christmas with the addition of a bonus track we will talk about later.

A cursory search for “Dean Martin Christmas CD” at Amazon reveals 14 different “albums”. Keep in mind the man recorded less than 20 songs that could actually be considered “Christmas” songs. In 1992, something called CEMA Special Markets leased these songs and came up with Season’s Greetings. I actually bought this thing despite it’s ridiculously bargain-basement cover “art”. I bought it because it had two songs on it that the previous Dean Christmas compilation I bought didn’t have; the great originals from A Winter Romance, “Out in the Cold Again” and “It Won’t Cool Off” (we’ll talk about these two songs again). All the tunes on it are good, I suppose, but you can do better.

In 1998, Capitol and Reprise Records were merged under the same umbrella and that year saw the release of two CDs that presented for the first time together Dean’s recordings from both labels. The Very Best of Dean Martin: The Capitol and Reprise Years is self-explanatory. Making Spirits Bright was a thrill for me and I bought it that year it was new. Great artwork and packaging and 15 of Dean’s best holiday tunes. What it contains is every true “Christmas” song from A Winter Romance except the two lost gems I mentioned before – “Out in the Cold Again” and “It Won’t Cool Off” – and “Winter Wonderland”. It also has every season-appropriate tune from The Dean Martin Christmas Album except “White Christmas”; “Winter Wonderland” and “White Christmas” Dean recorded for both records. This CD has Capitol’s “White Christmas” and Reprise’s “Winter Wonderland”. So, this fine collection gives you almost all of it. But for me, I wish it was sequenced chronologically. If you see this one, buy it.

2004’s Christmas With Dino goes one better. With great cover art borrowed from one of my two favourite Dean Martin albums, Dream With Dean, this one has all the tracks the previous collection has but contains both versions of the three songs Dean did on both records. It also adds his first Christmas recording, the excellent 1953 single “The Christmas Blues” – but this one also fails to include “Out in the Cold Again” and “It Won’t Cool Off”. Why do these two keep getting the shaft? Sadly, this CD is hard to find cheap and may even be out of print.

My Kind of Christmas hit the shelves in 2009 and looks to me like a bit of a cash-grab. It contains the bulk of the best Dean Christmas songs including “The Christmas Blues” and this one also includes a bonus one-off from 1963. That November, Frank’s Reprise Records released a Christmas album featuring various artists that was called Frank Sinatra and His Friends Want You to Have Yourself a Merry Little Christmas. The record was closed by Dean singing “Silent Night” in a medley with a tune called “Peace on Earth” that was written by Peggy Lee and this album’s producer, Sonny Burke. It’s lovely. What is not lovely is the inclusion of “Winter Wonderland (The Swingin’ Yuletide Mix)” and another sketchy novelty, “I’ll Be Home for Christmas” rigged up as a “duet” with actress Scarlett Johansson. Why? Caveat Emptor. And to wrap things up, I’d say beware of Dino’s Christmas, released in 2014. This budget release has only ten songs and one of them is the non-Christmasey “Brahm’s Lullaby”. But y’know what’s funny? “Out in the Cold Again” is on this!

Strolling through the mall in December you might also hear the lovely opening strains of Dean’s “Baby, It’s Cold Outside” but then detect that something is amiss. Actually, that something is “a Miss”. Miss Martina McBride recorded a duet with Dean on this tune in 2006. I mentioned Miss McBride singing also with Elvis Presley on a Christmas duet. And you talk about Christmas Caveats. Talk about recycling someone’s Christmas music; maybe you can describe to me what Martina is up to. In 1998, she released her fifth studio album, her first Christmas release, White Christmas. The very next year, the album was reissued with a different cover and two additional songs. Then in 2007, the album was fleshed out even more and her phoney duet with Dino was added to the track listing. Finally in 2013, the album was resequenced and retitled and offered to the unsuspecting public, this time featuring duets with Dean and with Presley on “Blue Christmas”. By the way, Martina’s most recent album is her “second” Christmas album, 2018’s It’s the Holiday Season, the last album Patrick Williams worked on before his death. But back to our paisan.

Ideally, what you do is buy A Winter Romance and The Dean Martin Christmas Album – after all, that’s only two albums. Additionally, seek out one of the three Christmas With the Rat Pack CDs out there. You get many great songs from the Chairman and the few Christmas songs recorded by Sammy Davis. Dean shows up as well and one or all of these CDs will feature the previously mentioned “Peace on Earth / Silent Night” and also two duets with Frank, one “A Marshmallow World” from the Christmas edition of The Dean Martin Show from 1967 and an “Auld Lang Syne” from 1970.

If you’re looking for a compilation, Christmas With Dino may be the best bet but it also may prove hard to find. I have Making Spirits Bright and can vouch for it. Liner notes by Joseph Lanza, great art, most of the good songs and I give it points for coming up with an original title and a pretty good one at that. Hope this helps you find the best way to add Dean Martin to your Yuletide listening rotation.


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