Top 10 Classic Christmas Songs to Add to Your Holiday Playlist

The holiday season wouldn’t be complete without a song or two! We often associate Christmas songs with happy memories of past holidays. Additionally, singing our favorite holiday hits can be a huge stress reliever. If you’re an older adult who loves Christmas songs, you’re in the right place. Here are 10 classic songs to add to your holiday playlist this Christmas season.

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1. “White Christmas” by Bing Crosby

“White Christmas” has practically become synonymous with the holiday season. Written by Irving Berlin in 1942, it actually didn’t appear in the movie White Christmas. Bing Crosby first sang this holiday classic in the 1942 film Holiday Inn, starring Fred Astaire and Marjorie Reynolds. Although many artists have covered this song, Bing Crosby’s version will always be the definitive one. And, if you’ve never watched the holiday classic White Christmas, do yourself a favor and watch it this Christmas season. It’s truly Bing Crosby at his best!

2. “It’s Beginning to Look a Lot Like Christmas” by Perry Como

If the holiday spirit hasn’t hit you quite yet, you may feel a little more festive after listening to “It’s Beginning to Look a Lot Like Christmas.” The song was released to critical success in 1951, and it continues to be a favorite to this day. It describes the excitement and joy of seeing the world prepare for Christmas: toys in store windows, candy canes, and carols filling the air. “It’s Beginning to Look a Lot Like Christmas” truly captures the holiday spirit. No wonder so many people consider it to be a timeless classic!

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3. The Christmas Song (Chestnuts Roasting on an Open Fire)” by Nat King Cole

Nat King Cole had one of the most beautiful voices to ever grace the music industry, and “The Christmas Song” showcases it perfectly. The lyrics paint a picture of a cozy and idyllic Christmas scene. Who doesn’t feel warm and cozy when they hear the opening lines? The gentle, soothing tempo combined with the vivid imagery make this song an auditory delight. It truly captures all the simple joys of the holiday season.

4. “It’s the Most Wonderful Time of the Year” by Andy Williams

Did you know that there’s a link between this song and the 1964 sitcom Gilligan’s Island? George Wyle, who composed the Gilligan’s Island theme, also wrote this song! Interestingly enough, Andy Williams himself became synonymous with Christmas, thanks to his fondness for garish sweaters and frequent appearances on holiday TV specials. In fact, it earned him the nickname “Mr. Christmas.” If you’ve ever pondered over the “scary ghost stories” lyric, then ponder no more. This references a popular Victorian holiday tradition that Charles Dickens himself may have inspired.

5. “A Holly Jolly Christmas” by Burl Ives

Johnny Marks, the songwriter responsible for “Rockin’ Around the Christmas Tree” and “Silver and Gold”, also penned this holiday smash-hit. The song was first featured in the beloved 1964 classic Rudolph the Red-Nosed Reindeer. To say “Have a Holly Jolly Christmas” is timeless is an understatement. In fact, it charted on the Billboard Top 100 list in 2017, 52 years after its original release. Talk about a song with staying power! We feel it’s due in no small part to Burle Ives and his warm, distinctive voice.

6. “Rudolph the Red-Nosed Reindeer” by Gene Autry

Speaking of Johnny Marks, we can also thank him for this beloved Christmas classic! Intriguingly, Mr. Mark’s brother-in-law is responsible for creating the character of Rudolph. Robert L. May, a thirty-four-year-old copywriter for a Chicago department store, wrote the story as a promotional gift for the customers. If “Rudolph the Red-Nosed Reindeer” is one of your favorite Christmas songs, then you should send a thank-you note to Gene Autry’s wife. While the singer didn’t want to do this song, his wife convinced him to record it. Considering it’s the second-best-selling Christmas song of all time, we’re certain Gene Autry sent his wife a few thank-you notes, too!

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7. “Santa Claus Is Coming to Town” by Gene Autry

This song might not be as popular as it is today, were it not for a little wifely persuasion. In this instance, comic Eddie Cantor thought the song was too childish and didn’t want to perform it at all. At his wife’s insistence, Mr. Cantor sang this song during a live broadcast of the Macy’s Thanksgiving Day Parade. It was an instant hit, selling 300,000 copies by Christmas Day. It’s a Christmas classic, covered by everyone from the Jackson 5 to Frank Sinatra. And, of course, “The Singing Cowboy” himself, Mr. Gene Autry!

8. “Have Yourself a Merry Little Christmas” by Judy Garland

If you’ve ever seen the 1944 classic Meet Me In St. Louis starring Judy Garland, then you witnessed the first-ever performance of this Christmas classic. The song’s melancholic tone and bittersweet lyrics have resonated with listeners for generations, making it a beloved holiday classic. While many artists have put their spin on it, there’s something truly special about Judy Garland’s version. The original version was so somber that Judy refused to sing it. She reportedly said, “‘If I sing that, little Margaret [O’Brien] will cry and they’ll think I’m a monster.'” Thankfully, the composers listened to Judy and tweaked the lyrics. “Have Yourself a Merry Little Christmas” reminds us that even in difficult times, we can find joy and hope. It’s not hard to see why this holiday hit has resonated with so many generations.

9. “Jingle Bell Rock” by Bobby Helms

Currently, “Jingle Bell Rock” has over 600,000 streams on Spotify and even charted at number three on the Billboard Hot 100 last year. It’s not an exaggeration to say that this song has been popular since the day it was released in 1957. Bobby Helms’s version is probably still the best-known, though other artists have covered it over the years. It’s cemented itself as a Christmas classic and deserves a spot on any holiday playlist.

10. “Let It Snow! Let It Snow! Let It Snow!” by Dean Martin

While more of a winter tune than a Christmas carol, this song has become a festive staple. Written in 1945, it’s been featured in movies like Die Hard and The Family Man. Patsy Cline, Carly Simon, and even the Carpenters have all recorded their renditions. Of course, Dean Martin’s version is one of the most popular—and for good reason. It’s breezy and carefree, the perfect song to get even the most hard-bitten Scrooge into the holiday spirit. Or, if you’re enjoying it outside the Christmas season, a wintery mood.