By far and with a difference, Christmas is the most popular celebration on the planet. And not without reason, I will add, as it involves wild partying, feasting, gift exchange, and beautiful moments with our family and friends.

And to celebrate even more beautifully this year, I have prepared for you the ultimate classic playlist of Christmas songs that is like good whiskey; the older it gets, the more wonderful it is.

1. Bing Crosby - "White Christmas" 

And we start our list with the most popular song, as the single has sold over 50 million copies worldwide and is also in the Guinness World Records. Written by Mr. Irving Berlin, it was first performed live on a radio station on Christmas of 1941, just a few weeks after the attack on Pearl Harbor. A few months later, it was recorded by Bing Crosby in 1942, in just 18 (!) minutes.

The song is melancholic and at the same time warms your heart. And of course, it has been covered countless times (over 500) by artists from Bob Marley and Elvis Presley, to Lady Gaga and Gwen Stefani.

"I'm dreaming of a white Christmas

Just like the ones I used to know

Where the treetops glisten and children listen

To hear sleigh bells in the snow"

2. Frank Sinatra - "Have Yourself a Merry Little Christmas"

Second on our list, we cannot miss out on Frank Sinatra's rendition of "Have Yourself a Merry Little Christmas". The original version belongs to Judy Garland in 1944, but Frank famously rearranged and even changed some of the lyrics when he recorded it in 1957. He took it to such a level that Judy Garland later sang it with his lyrics, not her own!

"Through the years we all will be together

If the fates allow

Hang a shining star upon the highest bough

And have yourself a merry little Christmas now"

3. Nat King Cole - "The Christmas Song"

We continue unabated with the incredible voice of Nat King Cole, first recorded in 1946, second in 1953, third in 1961. By himself. Yes, he recorded it 3 times!

The creator of the song, Mel Tormé, had stated that he wrote it in the summer heat, thinking it would cool off if he made icy thoughts... And through the words he wrote on a piece of paper 'Chestnuts roasting..., Jack Frost nipping..., Yuletide carols..., Folks dressed up like Eskimos.' the song was born after 40 minutes!

"And so I’m offering this simple phrase

To kids from one to ninety-two

Although it’s been said many times, many ways

Merry Christmas to you"

4. Dean Martin - Let It Snow! Let It Snow! Let It Snow!

A song dedicated to snow, without mentioning holidays and Christmas, and yet it is one of the most popular Christmas songs!

Written on the hottest day of 1945 by two talented musicians who, instead of going to the sea to cool off, thought why not write a winter hit. Well, and the performance later in 1959 by Dean Martin is definitely the best of all!

"And the fire is slowly dying

And, my dear, we're still goodbying

But as long as you'd love me so

Let it snow! Let it snow and snow!"

5. Ella Fitzgerald - "Frosty The Snowman"

The song was first recorded in 1950, and 10 years later in 1960, jazz singer Ella Fitzgerald covered it in this dreamy rendition.

Although the song doesn't directly mention Christmas in the lyrics, it tells the story of a snowman who came to life and went to play with the children on a sunny winter day... A very sunny day, as in the end the snowman melted and said to them with a Terminator line, "I'll be back." Pretty cheeky, huh?

For Frosty the snowman

Had to hurry on his way

But he waved goodbye

Saying, "Don't you cry

I'll be back again some day"

6. Brenda Lee - "Rockin' Around the Christmas Tree"

The song was recorded in 1958, and while it has been covered several times since then, the first version by Brenda Lee dominates with over 25 million sales worldwide.

The creator of the song was Johnny Marks, and if his name doesn't ring a bell, I'll tell you that the previous hit he wrote was "Rudolph the Red-Nosed Reindeer." And as if that wasn't enough, he personally requested Brenda Lee to sing his piece, at just 13 years old.

"You will get a sentimental feeling when you hear

Voices singing, let's be jolly

Deck the halls with boughs of holly"

7. Andy Williams - "It's the Most Wonderful Time of the Year"

We continue with a song written and recorded in 1963, for the first Christmas album of Andy Williams. And of course, it became a huge success. The song refers to the festive days when friends and relatives gather to celebrate together, eating, partying, and telling scary stories. What a wonderful time of the year indeed it is!

There'll be parties for hosting

Marshmallows for toasting

And caroling out in the snow

There'll be scary ghost stories

And tales of the glories of

Christmases long, long ago

8. Bobby Helms - "Jingle Bell Rock"

Signature song for this artist as Jingle Bell Rock is synonymous with Bobby Helms. The first recording was made in 1957 and remains timeless.

The song ended up in court as Bobby Helms and his guitarist fought for the rights to the song (they had none). They were never vindicated even until their death. Nevertheless, his rendition will forever remain in our history and hearts.

Giddy-up jingle horse, pick up your feet

Jingle around the clock

Mix and a-mingle in the jinglin’ feet

That’s the jingle bell rock

9. Perry Como - "It's Beginning to Look a Lot Like Christmas"

Although performed by many various great artists, the recording by Perry Como in 1951 is the one that has been etched in our minds and hearts. A month later, Bing Crosby also recorded it, and it naturally became a hit, but not like Perry Como's. And the song talks about nothing else but Christmas!

"It's beginning to look a lot like Christmas
Soon the bells will start
And the thing that'll make 'em ring is the carol that you sing
Right within your heart"

10. Eartha Kitt - "Santa Baby"

We close our festive playlist with the iconic Eartha Kitt! In this particular song, our beloved Eartha literally asks for yachts and helicopters from Santa Claus.

It was released in 1953 and, of course, it caused mixed reviews and reactions, as it was considered quite provocative for the puritanical era. Since then, there have been numerous covers by singers such as Madonna, Kylie Minogue, Taylor Swift, and Ariana Grande. Who wouldn't want to, right?

Santa baby, I want a yacht and really that's not a lot

Been an angel all year

Santa baby, so hurry down the chimney tonight

Happy holidays, my dear reader, and whatever you do, make sure to always have the appropriate musical background!