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Music Monday: 5 Nostalgic Songs x 3 Timeless Versions = 15 Picture-Perfect Holiday Tunes


Seems like every artist wants to put out a Christmas album some time during their career and inevitably, they fall back on doing a few of the “classics.” Some provide safe, traditional renditions of each song, staying faithful to the composer’s vision. Others change it up a bit, looking to bring new feelings or flavors to the mix.

From a nostalgic point of view, there are so many songs that give rise to warm, positive feelings during the Christmas season that it’s hard to narrow them down.  But we think we’ve found a few fabulous holiday songs for your listening pleasure.

Today’s Music Monday Mix takes five wonderfully nostalgic and classic versions of holiday songs and pits them against two later covers.


Our questions to you: Do you prefer a classic version, a modern version, or perhaps one in between? Does each version stand on their own?  Which one makes you feel the most nostalgic? Do you think there are any recent Christmas songs written today that will become “classic” Christmas songs 20 years from now?

Have Yourself a Merry Little Christmas

Frank Sinatra – 1957

Carpenters – 1978

Sam Smith – 2014

Snapshot: “The song first appeared in a scene in Meet Me in St. Louis, in which a family is distraught by the father’s plans to move to New York City for a job promotion, leaving behind their beloved home in St. Louis, Missouri, just before the long-anticipated 1904 World’s Fair begins.”  Source: Wikipedia

Sleigh Ride

Johnny Mathis – 1958

Ronettes – 1963

MercyMe – 2015

Snapshot: The orchestral version composed by Leroy Anderson was “first recorded in 1949 by Arthur Fiedler and the Boston Pops Orchestra.” Currier & Ives [“It will nearly be like a picture print by Currier & Ives”] were not artists, but rather “a popular printing company in the 19th century. The company closed in 1907, 43 years before the song’s lyrics were written.” Source: Wikipedia

White Christmas

Bing Crosby – 1954

The Drifters – 1955

Kelly Clarkson – 2013

Snapshot: “‘White Christmas’ is a 1942 Irving Berlin song reminiscing about an old-fashioned Christmas setting. According to the Guinness World Records, the version sung by Bing Crosby is the best-selling single of all time, with estimated sales in excess of 100 million copies worldwide.” Source: Wikipedia

The Christmas Song

Nat King Cole – 1961

John Denver – 1975

Brett Eldredge – 2016

Snapshot: “‘The Christmas Song’ (commonly subtitled ‘Chestnuts Roasting on an Open Fire’ or, as it was originally subtitled, ‘Merry Christmas to You’) is a classic Christmas song written in 1945 by Bob Wells and Mel Tormé. According to Tormé, the song was written during a blistering hot summer. In an effort to ‘stay cool by thinking cool’, the most-performed (according to BMI) Christmas song was born.” Source: Wikipedia

Baby It’s Cold Outside

Dean Martin – 1959

Zooey Deschenel & Leon Redbone  –  2003

Michael Buble & Idina Menzel – 2014

Snapshot: “A couple from Minnesota has re-imagined the classic Christmas song “Baby It’s Cold Outside” for a 21st-century audience, changing the song’s lyrics to emphasize the importance of consent.” Source: CNN


At The Nostalgia Diaries, our goal is to help you simplify, enhance, and engage your lives by focusing on the most important things: remembering, appreciating, believing, and becoming. It’s all about celebrating the past to create better days today.

P.S. Don’t forget to follow our colorful, creative spaces on Facebook, Instagram and Pinterest. We’re fun and happy and whimsical and nostalgic over there, too. Pinky swear.

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