I love Christmas music. Music in general appeals to my imagination and Christmas music in particular has a singular effect on me. It has always had attached to it a feeling of nostalgia; for one’s own youth but also for bygone eras. Wherever you are, it can summon up the living rooms of your childhood where you sat with family and friends admiring the tree and the fire. It can also lead you to imagine the parlours of another time, where families sat quietly and listened to the music of the season on their radios or record players. Even more so than surf music in summer, Christmas music goes hand-in-hand with the appeal of the season and is, in fact, a big part of what makes this time of year so special.

The “Christmas Season” starts in our house on the Saturday before the last full week of November. We used to wait until December but we found that it was taking several days to get all of the Christmas stuff up. So, it’s on that Saturday late in November that the Christmas tree goes up and the Christmas music begins to play and every year I love it all over again. Every year, though, I think the same thing: certain Christmas music goes better at certain times throughout the 4-6 weeks you are listening to it. For example, during the last week of November, I try to avoid songs like Billy Eckstine’s beautiful “Christmas Eve”. A gentle and evocative song, it makes the biggest impact when it’s listened to when Christmas morning is only hours away. I feel like I want to build up to that feeling. On the other hand, there is plenty of Christmas music that is more playful and can help to get you primed for the wonderful emotions to come and that’s the stuff that can be listened to early. Every year I feel like Christmas music should be handled as if the season was a musical – sequenced in such a way that it follows the progression of feelings and emotions you go through as the season moves along.

Say you decorate your house and the Christmas season starts for you every year on November 18th. Say the first thing you listen to is Bing Crosby’s immortal Merry Christmas album, as is often the case in our house. It is possible, then, to listen to this Christmas gem on November 18th and then not get back to it again until maybe Christmas Day. If you have copious amounts of Christmas music and you want to get it all listened to you may not have a chance to listen to certain albums again. The answer of course is to live free from ‘listening rules’ and listen to what you want, when you want and we probably hear Bing over and over during the season, anyways. But my point is; Christmas starts and you can’t wait anymore to get to Bing. But he is exactly what you want to listen to in the shank of the season, too. Say, the week before Christmas. So, early on is when it may make sense to listen to the less important stuff – the ‘Third Tier’ stuff. Maybe it’s important to you – as it is to me – to own all five of Harry Connick’s Christmas albums. But his Music from ‘The Happy Elf’: Connick on Piano Vol. 4 soundtrack does not exactly elicit the warm and fuzzies in you. This is a perfect one, then, to listen to at the end of November; to check it off and get it ‘out of the way’, so to speak. Hope this makes sense.

So, if Christmas is a musical, then Act One could be called “A Saturday in November”. A perfect ‘curtain-raiser’ is “It’s the Most Wonderful Time of the Year”. Introduced in 1963 by Andy Williams, it’s the perfect song to get things rolling. The lyrics celebrate the joys to come. They list not the wonderful things you’ve been doing but the wonderful things you will do. And, really, the lyrics are not all that concerned with Christmas Day itself. They depict holiday traditions and tell of excited children. There are “gay, happy meetings” featuring “parties for hosting, marshmallows for toasting and caroling out in the snow”. It gets you excited as it runs down the list of fun things on the horizon. Also on Andy’s first Christmas album is “Happy Holiday/The Holiday Season”. The first half of this medley dates from 1942 and its use in the perennial film favourite Holiday Inn while the second half springs from the creative mind of Kay Thompson. Andy and his brothers got their big break as an integral part of singer Thompson’s act in the late 1940’s. Kay – with whom Andy had a short-lived affair – wrote “The Holiday Season” as a companion piece to everyone’s second-favourite Bing Crosby number from Holiday Inn. She also put her own spin on “Jingle Bells” and Andy included “Kay Thompson’s Jingle Bells” and “Happy Holiday/The Holiday Season” on his first Christmas album in 1963. The latter works as a simple and obvious declaration: “It’s the holiday season so hoop-de-doo…”

Another Andy tune that is something of a companion to “Most Wonderful Time” is “Christmas Holiday”. From his second Christmas album released two years after his first, this is another song that runs down a litany of the social and the edible joys to come. “Yuletide, good cheer. Christmas is here…Christmas time is here”

In 1964, the husband-and-wife team of Steve Lawrence and Eydie Gormé put out a wonderful Christmas record called That Holiday Feeling! The title track is in a similar vein as the previous Andy songs and feels like it was designed to kick off the proceedings. The couple’s fine record has actually a few great songs for early listening such as “Let Me Be the First to Wish You Merry Christmas” – “Let me be the first to wish you merry Christmas although the holiday is still some time away” – and “That Old Christmas Spirit”, the lyrics of which look forward, mentioning the neighbour trimming the tree in the yard and the appearance of Christmas music on the radio.

Frank Sinatra’s contributions to Christmas music are maybe not what you’d expect. However, one gem from his Columbia Records days is “Christmas Dreaming”. This pleasant song is a delight and is perfect for early in the season because of its lyrics: “I’m doing my Christmas dreaming a little early this year. No sign of snow around…” Harry Connick does a faithful version on his first Christmas record, When My Heart Finds Christmas.

Also perfect for listening to early on is a song like Billy Joel’s “She’s Right on Time”, a typically polished tune from Joel from his Beatle-esque album The Nylon Curtain from 1982. “Turn on all the Christmas lights, ’cause baby’s coming home tonight…” It’s a good example of a technically non-Christmas song on a non-Christmas album that you may run into throughout the year. You don’t really want to hear it in June – or it’s effect on you will be blunted – so you should be sure to listen to it during the Christmas season. Another non-Christmas song that mentions Christmas in its lyrics is Canadian Joni Mitchell’s “River”, a gentle song that lends itself well to a piano treatment. Perhaps the finest version I’ve heard is by one Robert Downey, Jr. from his Ally McBeal days.

“December Time” is a pleasant song from Robert Goulet’s delightful first album of Christmas music, This Christmas I Spend With You (1963). Described on the back cover as having been sent to him by a songwriter in Calgary, it is suggested that the song is reminiscent of “The Christmas Song” and “you won’t be surprised if it becomes one of those haunting melodies which linger year after year”. “The mistletoe that’s growing will soon be picked for showing…the fancy coloured lighting are certain signs the yuletide’s growing near”

Bing Crosby, of course, is “the voice of Christmas”. What may escape some casual listeners is the fact that Bing, in addition to his iconic earlier recordings, released Christmas music throughout his 50 year career. Indeed, Der Bingle recorded “Silent Night” in 1935 and “Peace on Earth/Little Drummer Boy” in 1977. One of his lesser-known Christmas recordings is perfect for listening at the start of the season and it’s nice to hear him at this early juncture; hearing his voice at this time can serve as a primer for the great music to come. “It’s Christmas Time Again” – its very title heralds the advent of the season – is on 12 Songs of Christmas, an album from 1964 that Bing recorded with Frank Sinatra and Fred Waring. Interestingly, this record was initially released in August!

“Winter time brings Christmastime…” John Gary wrote and recorded “Wintertime and Christmas Time” on his 1964 The John Gary Christmas Album. This song is a serene number that lists many of the deeply satisfying elements of the coming holiday. John Gary was an interesting guy; and not just because my brother’s name is John and I’m Gary. His tenor voice made him a hard sell on the popular market and he eventually grew a beard and performed with acoustic guitar. A former U.S. Marine, he held many underwater swimming records (breath control) and even invented an underwater propulsion device.

Probably the biggest country music band of all-time, Alabama, released “Christmas in Dixie” in 1982. The song takes us on a trip through the American South and references all the places – including Graceland – that are preparing for the holidays. People maybe don’t know that singer Mel Tormé, a vocalist considered by many second only to Francis, wrote the lyrics to perhaps the second-most revered holiday song ever, “The Christmas Song” (music by Robert Wells). Much later, Mel took pen in hand to write a little opening number called “Just Look Around” that he paired in a medley with “Have Yourself a Merry Little Christmas” and recorded on his Christmas Songs album for Telarc in 1992. “Just look around, all the signs are there. There’s a special kind of feeling of excitement in the air. It’s a family kind of season, it’s the happiest of times…I can hardly wait to say ‘goodbye, November, step aside and make way for December’…” Check out this swingin’ album from Big Bad Voodoo Daddy. Their It Feels Like Christmas Time was released in 2013 and features an excellent “Walking in a Winter Wonderland” – and I just now realize that they add the “Walking in a..” to the title; you don’t often see that. But it’s the title track that fits in with the rest of these songs. It announces the onset of the feelings associated with the yuletide season and name checks some of the annual participants; “Christmas time is coming and I’m already humming Christmas tunes from many years ago. I love them so. All the leaves are changing…and the Christmas lights in every town. The Grinch, Rudolph and Charlie Brown…”

I always think that instrumental music is good to listen to at the very start of the holidays, as well. The familiar melodies that you easily recognize can fill your heart with what Bing Crosby calls a “mellow glow” without necessarily filling your ears with the specifics of the lyrics that may mention Christmas Eve or Christmas Day, etc. Also I feel like there comes a groovy, smooth-jazz-office-Christmas-party vibe from instrumental music. A few full albums I can suggest include Al Caiola and Riz Ortolani’s sumptuous Sound of Christmas from 1967. “One Bright Star’ and “Bossa Nova Noel” are particularly delightful. Speaking of bossa nova, this breezy Brazilian export lends itself well to Christmas music. One Christmas while I was searching for bossa-flavoured Christmas tunes, I ran into Lori Mechem. Originally from Indiana, pianist and composer Mechem operates a jazz school in Nashville, The Jazz Workshop. Her 2005 album Brazilian Christmas is an absolute treat. Jack Jezzro is another artist that works out of Nashville who digs himself a bossa nova Christmas. The guitarist has been a part of the venerable Nashville String Machine, a collective that has played on 1,171 albums since 1972. Mechem and Beegie Adair play on Jezzro’s Bossa Nova Christmas from 2009. Vinnie Zummo is a New York-based session guitarist who made whatever name he has playing with Joe Jackson. I’ll always be grateful for Vinnie’s ridiculously titled but delightful A Retro Cool Bossa Nova Christmas album from 2001, on which he produces some lovely mellow sounds.

So, let’s get this party started – but at the same time be respectful to those who don’t care to hear Christmas music until the middle of December. Here’s a playlist that lets the holiday spirit come upon you incrementally, perfect for a Saturday in November.

“It’s the Most Wonderful Time of the Year” — Andy Williams

“Christmas Dreaming” — Frank Sinatra

“Let Me Be the First to Wish You Merry Christmas” — Steve Lawrence and Eydie Gormé

“Happy Holiday/The Holiday Season” — Andy Williams

“December Time” — Robert Goulet

“It’s Christmas Time Again” — Bing Crosby

“That Holiday Feeling” — Steve Lawrence and Eydie Gormé

“She’s Right on Time” — Billy Joel

“River” — Robert Downey, Jr.

“Wintertime and Christmas Time” — John Gary

“Christmas in Dixie” — Alabama

“Christmas Holiday” — Andy Williams

“Just Look Around / Have Yourself a Merry Little Christmas” — Mel Torme

“It Feels Like Christmas Time” — Big Bad Voodoo Daddy

“Bossa Nova Noel” – Al Caiola & Riz Ortolani

“I’ll Be Home for Christmas” — Lori Mechem

“Santa Claus is Coming to Town” — Jack Jezzro

“Jingle Bells” — Vinnie Zummo