Christmas music doesn’t just begin playing in December—it kicks off in November, which says a lot about how merry this season is. It’s more of a challenge to make a Christmas playlist because, unlike Halloween, there are a lot, and I mean a lot, of great Christmas songs from the 1950s, 1970s, 1980s and even more recent years. 

There are a lot of things to consider: this playlist has to be fun, nostalgic, hopeful and joyful. But most importantly, it has to evoke memories of Christmases past. Here are six quintessential holiday songs that are guaranteed to evoke that feeling.

A Holly Jolly Christmas by Burl Ives:

This is a classic Christmas song full of joy and happiness. The catchy guitar riffs make you want to dance while decorating a Christmas tree. Featured in the 1964 Christmas movie “Rudolph the Red Nosed Reindeer,” the bells and drums in this song have become a timeless favorite.

Jingle Bell Rock by Bobby Helms:

As you are wrapping your gifts with friends or family, with this tune in the background, you can’t help but look forward to the Christmas gatherings and reunions, where you’re surrounded by family and friends. This song has been covered many times by artists around the world, but Bobby Helms’ version is the most famous and beloved out there. 

It’s The Most Wonderful Time Of The Year by Andy Williams:

This is a unique song, as the introduction is a fascinating buildup to begin the song. This song sets the mood for any Christmas party or gathering, it tells us what Christmas is for: how family and friends help this season be the happiest time of the year. It sings to us all the Christmas activities you can do during this season— caroling, marshmallow toasting, winter wonderland-themed parties— the possibilities are endless. 

Have Yourself A Merry Little Christmas by Frank Sinatra:

This song perfectly brings back nostalgia about past Christmases. Sinatra’s relaxing voice is very soothing and calming. “From now on our troubles will be out of sight”— isn’t that what Christmas is about? It’s a time to forget about our struggles and embrace the people around us. This song inspires gratitude for Christmas and brings hope for future holidays. 

All I Want For Christmas Is You by Mariah Carey:

This song has been #1 on the Billboard Hot 100 for five years straight, from 2019 to 2023 during the holiday season. This is undoubtedly the most famous modern Christmas song, no other song comes close. A great song to dedicate to someone, whether as a simple thank-you gift or even something more meaningful. Played on the radio and on everyone’s devices all December long,  it reminds us that no laptop, money, book, or anything really will match the ideal gift of the person we love.

Last Christmas by Wham!:

The Christmas song will be “All I Want For Christmas Is You” or this classic holiday song about heartbreak. Speaking to themes of love, the spirit of the season and being hopeful. Everyone around me tells me how good this song is, my friends, family and colleagues. The truth is, this is a phenomenal song. This song reminds us that Christmas can be a time for new beginnings, whether it’s moving past a heartbreak or meeting someone new.