It’s that time of the year again. Christmas.
And before you say “well Christmas does more harm than good for its traditionalism pushing and to an extent, especially in modern times, capitalism”. I would not deny it. In fact, numerous works throughout history have gone out to parody the very forcing nature of Christmas Eve. The spirit has gone downhill noticeably since we grew up and took up responsibilities. One has to hit a certain age when they have to cope with the fact that Santa Clause does not exist, and another certain age when we realize how annoying it is hearing "All I Want For Christmas Is You" for the gazillionth time.
But in retrospect, there is something so special and exquisitely nostalgic about sitting by the fire during harsh winter, enjoying my favorite hot beverage and being with my beloved ones. Who could turn down offers for chocolate chip cookies? It might not be the most wonderful time of the year for the majority of depressing folks, but at least the ribboned pine trees are eye-catching, the turkey is not burnt (just yet) and the music is (chef’s kiss) transplendid.
Some honorable mentions: Eartha Kitt’s Santa Baby, Sleigh Ride, Rudolph The Red-Nosed Reindeer, Silent Night (any single cover of it)

1. Merry Christmas Darling (1970)

Topping this list is of course a Carpenters piece which I have held very dear in my heart since my early teenage years. Swept away by Karen Carpenter’s smooth-as-silk voice, Merry Christmas Darling melts my heart every single time I give it a listen and touches me on so many emotional levels, it would be a crime to myself if I don’t let this come out on top.
Well, nobody does Christmas better than the Carpenters. Their Christmas Portrait record with renditions ranging from Ave Maria to Sleigh Ride is enough for my Christmas wish list.Also noted that there are two versions of Merry Christmas Darling, 1970 single which came along at a very early stage of the Carpenters’ career and the 1978 take with a more retouched, smoother direction on Karen’s vocal part. Both of which, in my opinion, are worth putting on repeat all day long. Christmas essential.

2. The Andrews Sisters - Mele Kalikimaka

National Lampoon’s Vacation was fun. Christmas Vacation, oh, now we’re talking! Undoubtedly peak 1980s comedy, we can’t talk about National Lampoon’s Christmas Vacation without talking about the scene in which Chevy Chase’s character is looking out of the window thirsting over a beautiful young lady by the pool with this song playing in the background. Being already an Andrews Sisters fan myself prior to watching the film, Mele Kalikimaka is up there with some of my favorite Andrews Sisters tracks ever and of course, Christmas songs in general.
Bing Crosby, well known for the classic White Christmas also has a feature on Mele Kalikimaka and takes part in making it so iconic a Christmas modern carol.

3. Perry Como - (There's No Place Like) Home for the Holidays

More known for “It’s Beginning To Look A Lot Like Christmas”, Perry Como is good for other Christmas-y songs too.
Perry Como’s warm, honest-to-God (by any means necessary) voice in Home For The Holidays is American to the tee with the lyrics about “Pennsylvania to pumpkin pie” and my personal favorite, “from Atlantic to Pacific, geez the traffic is terrific”.
In fact, the Perry Como's classic was so beloved that the 1995 film Home For The Holidays featuring Holly Hunter (1993’s The Piano) was named after the song. There would be a period of time (around December of 2014) where I would play this song over and over again until it took over my head and got me unable to concentrate in my class for shit. Holly jolly times though.

4. Brenda Lee - Rockin’ Around The Christmas Tree

Brenda Lee’s iconic nasal voice has the ability to really get me in the Christmas mood, very much in the same vein as Wanda Jackson but less rough and dare to say, less rock-n-rolly. We all have heard “I’m Sorry” but not all of us could make the connection that “Rockin’ Around The Christmas Tree” was sung by the same person. I know. I am one of them. I am not ashamed.

5. Bing Crosby/David Bowie - Peace On Earth / Little Drummer Boy (Live performance)

One of my favorite Crosby and Bowie performances ever. The atmosphere, Bowie's God-given voice (especially the hauntingly divine "Peace on Earth...can it be?" part), such natural interactions between the two giants of two completely different generations in the music video that for a minute there kinda made you forget how big of names they are and just focus on the beautiful Christmas spirit.