On 4th day of Christmas … I listened to retro festive songs by Dean Martin, Bing Crosby, Ella Fitzgerald, Frank Sinatra + Barbra Streisand

(via Shutterstock)

Intangible though it might to say it but many Christmas songs are popular because they feel like the season.

And what is that feeling exactly?

It’s all kinds of cosiness and warmth, evoked by time with family and friends with snow falling outside – it may do that here in Australia in December where I live but it still endures as a hallmark of Christmas – food and drink to share and general sense of connection and wellbeing.

It is distilled, at least in this Christmas fan’s heart and mind, in all manner of retro songs by artists such as the following whose sound and style have come to mark even modern recordings of the songs that feature on many a Christmas album.

They sound and feel like Christmas and falling into the songs and many others of the time is to feel like you’re falling to the season itself which is no bad thing …

“Let It Snow! Let It Snow! Let It Snow!” by Dean Martin

(courtesy Apple Music)

Written in 1945 by lyricist Sammy Cahn and composer Jule Styne during a California heatwave, “Let It Snow! Let It Snow! Let It Snow!” is a perennial Christmas but also one of the songs most closely associated with Dean Martin’s festive output. First released on the Ohio-born singer’s The Dean Martin Christmas Album (1966), the song was re-released on 2013’s Dino’s Christmas which featured 10 of the singer’s best known Christmas songs (it was reissued in 2024). With voice described, quite justifiably, as “velvety”, he more than does justice to the track, imbuing with a joyous richness which really brings the lyrics to life and gives a heartwarming sense of how the very worst of things can actually create something cosy and wonderful.

“White Christmas” by Bing Crosby

(courtesy Amazon Australia)

The American singer and actor, who died in 1977 after a lifetime entertaining an adoring public, is perhaps best known for his rendition of “White Christmas”, written in 1942 for the movie Holiday Inn by the great Irving Berlin. Crosby, full name Harry Lillis “Bing” Crosby Jr., was in fact the first person to record and release the song as part of his starring role in the film, with his authoritative take on the song topping the charts for 11 weeks in the year of its release, reclaiming the #1 spot in 1943 and 1944. So popular was his recording of what quickly became a Christmas classic that it re-entered the charts a total of 12 times in subsequent years, proof that while plenty of very talented people have recorded the song in the decades since, Crosby has imbued his version with just the right, evocative sense of hope and nostalgic melancholy, becoming a beacon for everyone who doesn’t just miss snow at Christmas (since it’s not part of everyone’s festive experience) but the hallmarks of their Christmases past which can’t help but tug at our hearts.

“Sleigh Ride” by Ella Fitzgerald

(courtesy Vinyl.com.au)

Heatwaves seem to be the inspiration for a lot of snowy Christmas songs which makes sense: if you’re sweltering in oppressive heat, it’s understandable that the first thing you’d do is imagine yourself in colder climes. Penned by Leroy Anderson, “Sleigh Ride” first took form in July 1946 before being finished off in February 1948 with an inaugural performance in May of that year by the Boston Pops Orchestra. The song was initially music only, with Mitchell Parish only adding lyrics in 1950 at the request of publisher Mills Music. The song was first recorded and released by the inimitable Ella Fitzgerald (1917-1996) in 1960 on her Ella Wishes You A Swinging Christmas album which also featured classics like “Santa Claus is Coming to Town” and “Frosty the Snowman”. (It was followed in 1967 by Ella Fitzgerald’s Christmas which by way of stark contrast only featured religious Christmas material.) The singer’s take on the song is bright, alive, and vivaciously upbeat, perfectly capturing Anderson and Parish’s wistful hopefulness and happiness at what sleigh ride with someone you love can mean and how wondrously good it can be.

“The Christmas Waltz” by Frank Sinatra

(courtesy Discogs)

Written specifically for Frank Sinatra by Sammy Cahn and June Styne (Cahn resisted the idea at first telling Styne they couldn’t top “White Christmas), “The Christmas Waltz” was recorded in 1954 as the B-side to “White Christmas” and went on to be featured on both 1957’s A Jolly Christmas from Frank Sinatra and The Sinatra Family Wish You a Merry Christmas which came out in 1968. So perennially popular did the song become that it made annual appearances notes Wikipedia, on on Billboard magazine’s Holiday 100 chart from 2018 until 2022. The song is a wistfully beautiful evocation of what the season can mean and it comes to lusciously emotive life with Sinatra’s vocals filling with a rich soulfulness and cosy festiveness that perfects summons the season.

“Jingle Bells?” by Barbra Streisand

(courtesy Spotify)

While Barbra Streisand is rightly revered as one of the greatest singers of the 20th and 21st centuries, she is also one of those music artists who loves to try something new, imbuing her recordings with an impish sense of fun and pure delight. Case in point is “Jingle Bells?”, her rousingly mischievous and energisingly upbeat take on the classic song written by James Lord Pierpont, which apparently was not envisaged as a festive song when it published in September 1857 as “The One Horse Open Sleigh” but during the 1860s and 1870s, it acquired a wintery Christmas assoc nation and became a much-loved favourite of the season. It’s gone on to become one of the most commonly sung songs at Christmas, so happily ubiquitous that you can only imagine Streisand decided to really try something new with it to avoid sounding just like every other version. Her brilliantly vivacious take on Pierpont’s enduring classic featured on 1967’s A Christmas Album, establishing Streisand, who always fought for creative control over her career in an age where artists were expected to do as they were told by record labels, as someone who would pay homage to the beloved songs of the season but very much in her own way.

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