Entertainment Music The Top 40 Christmas Oldies Songs A countdown and history of the oldies era's greatest holiday tunes Share PINTEREST Email Print Michael Ochs Archives/Getty Images Music Oldies Major Artists Genres & Styles Top Picks 60s Hits 70s Hits Rock Music Pop Music Alternative Music Classical Music Country Music Folk Music Rap & Hip Hop Rhythm & Blues World Music Punk Music Heavy Metal Jazz Latin Music Learn More By Robert Fontenot Robert Fontenot Robert Fontenot Jr. is an entertainment critic and journalist focusing on classic rock and roll and published nationally for more than 25 years. Learn about our Editorial Process Updated on 05/24/19 The following 40 songs were picked by me, your Oldies guide at About.com, as being the best and most popular holiday tunes from the '50s, '60s, and '70s. Enduring annual airplay was considered in making the list, but also numbers of cover versions and overall Christmas "feel." Can you guess which Christmas song is which, based on the descriptions alone? On with the countdown! 40. Top 40 Christmas Oldies Songs: Number 40The Number 40 song was never released as a single, but was assembled from bits and pieces years after the band broke up! 39.At Number 39 is a song that swings harder and naughtier than most, partly because it's not really about Christmas at all! 38.The oldie but goodie at Number 38 isn't about Christmas, either, but it takes place then! 37.Number 37's holiday hit was sung by a man better known for "island music," which may be why it hit much bigger in the UK! 36.The oldie but goodie at Number 36 wasn't sung by a child, though it sounds like it... but it was inspired by one! 35.Coming in at Number 35 is a song sung by a 13-year-old... yet the Catholic Church banned it anyway! 34.The Number 34 spot is taken by a song that sat around for three decades before it was recorded... then took years to become a hit! 33.Number 33 in our countdown is reserved for a song that uses the same keyboard as "Bette Davis Eyes"! 32.The 32nd greatest Christmas song was made famous by a man who hosted TV Christmas specials for 40 years... and it's not Bing! 31.Our Number 31 Christmas classic features two extra reindeer... and a camel! 30.The song at Number 30 was made famous by a man who offended Americans at the World Series! 29.Making the list at Number 29 is the first antiwar Christmas song to hit the Billboard charts... and it was sung by a 16-year-old! 28.The song at Number 28 began the "Christmas #1" tradition in the UK... but it was actually recorded in the summer, and in New York! 27.Number 27 in our countdown is a Christmas song by a group that made it big singing about summer! 26.The song at Number 26 is the b-side of one of the most famous Christmas songs of all time... but it's not by the same artist! 25.The song coming in at Number 25 makes George Michael very sad. 24. Top 40 Christmas Oldies Songs: Number 24The Number 24 song on our countdown reminds us all that the reason for the season is often overlooked. 23.The song at Number 23 is modern R&B's greatest Christmas anthem... yet its creator never lived long enough to see it happen. 22.The holiday oldie coming in at Number 22 is an epic created by Philly Soulsters, led by a jazzman who jammed with Bird! 21.At the Number 21 position we have an old Czech folksong, recorded in a church! 20.The Number 20 selection in our countdown has become a standard in this version -- just don't buy anything expensive! 19.At Number 19 we have a blues song written by a "Christmas artist" but covered by a soul legend! 18.Number 18 was designed by a Beatle fan as a similar "thank you" to his own fans... but it made the radio anyway! 17.The Christmas classic at Number 17 is a political message that began life as a folk ballad about a horse race! 16.At Number 16 is a hit instrumental somehow morphed into a holiday standard! 15.Number 15 on our countdown was a wartime hit that had to be cleaned up in order to endure! 14.The Number 14 holiday oldie was a rock radio hit a full decade before it was ever released! 13.Number 13 on our countdown was written by a songwriter responsible for no less than four of the songs on our top 40 list! 12.Sitting at Number 12 in the countdown is another number inspired by a child... and a group named after three record executives! 11.The timeless classic in the Number 11 spot began as a coloring book, but wound up as the second most popular Christmas song ever! 10.The Number 10 song on our countdown may be the most famous Christmas song of all time... so famous, in fact, it destroyed itself! 9.At Number 9 is a song written to cool down the songwriter on a sweltering summer day! 8.Our Number 8 Christmas song is probably the sexiest in existence... but it was written by a Senator's niece! 7.The Christmas classic coming in at Number 7 is the first song to mention a "freeway"... and a tenth reindeer! 6.The song at Number 6 is a radical version of s standard that pleased its composer, even though he hated rock and roll! 5.The timeless classic coming in at Number 5 wasn't released as a single, and the album it was on flopped, but it's now a standard! 4.Our Number 4 song comes from an artist who gave the world not one but two oft-covered Christmas classics! 3. Top 40 Christmas Oldies Songs: Number 3Coming in at Number 3 is a song that was released before its star became famous -- and didn't become a hit until she did! 2. Top 40 Christmas Oldies Songs: Number 2The Number 2 selection in our countdown was made in only three takes, yet took seven years to even be released as a single! 1. Top 40 Christmas Oldies Songs: Number 1At Number 1 is the greatest Christmas oldie, a song which made it to the Top 10 even though it was rushed out on December 23rd!