Choosing a favorite Christmas song is almost as impossible – and potentially damaging – as choosing a favorite child. The fact is, there are enough wonderful holiday favorites out there to go around, and certain songs work better for certain occasions. Also, the whole thing is entirely subjective. There are thousands of people who would insist Mariah Carey sings the best Christmas song of all time, for example, while scores of others think the exact opposite is true.

Some songs have the power to convey the spirit of the Christmas season in special ways. These selections convey messages of hope, beauty, warmth, cheer, and joy like no other, and are enough to melt the ice from any Grinchly heart. 

Here are some of the best Christmas songs that should be included on every holiday playlist.

“Have Yourself A Merry Little Christmas,” by Judy Garland

This iconic holiday favorite was written by Hugh Martin and Ralph Blane in 1943 for the film “Meet Me in St. Louis” and first introduced by actress Judy Garland. During a scene on Christmas Eve, Garland’s character, Esther, sings the song to cheer up her five-year-old sister, Tootie (Margaret O’Brien).

The touching song was recorded by several famous names in music over the years, frequently making its way up the charts. Keyshia Cole, Michael Bublé, Sam Smith, Josh Groban, Phoebe Bridgers, and John Legend all released new versions of this old favorite.

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“The Christmas Song,” by Nat King Cole

No Christmas playlist would be complete with this aptly named title from Nat King Cole. “The Christmas Song” was written in 1945 by Robert Wells and Mel Tormé. The funny anecdote about this song is that it was dreamed up during a very hot summer.

“In the summer of 1945, the year before the song’s release, it was a very hot, sort of an oppressive summer that summer,” Tormé’s son explained during a 2017 interview with NPR. “And my father went to the house of his then-writing partner, a guy called Bob Wells. And Wells was nowhere to be seen. But there was a spiral pad at the piano. There were four lines sort of scribbled down on it in pencil – chestnuts roasting on an open fire, Jack Frost nipping at your nose, yuletide carols being sung by a choir, and folks dressed up like Eskimos.”

He continued, “And when Bob Wells eventually appeared he said, you know, Mel, I have tried everything to cool down. I’ve been in my pool. I had a cold drink. I’ve taken a cold shower. I’m nothing but hot. And I thought that maybe, you know, if I could just write down a few lines of wintery verse I could psychologically get an edge over this heat.”

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“I’ll Be Home For Christmas,” by Bing Crosby

Crosby’s beloved ode to the Christmas season cracked the top 10 on the Billboard Hot 100 chart for the first time in early January 2023.

“I’ll Be Home for Christmas” was written by lyricist Kim Gannon and composer Walter Kent. It was first recorded in 1943 by Bing Crosby as a way to honor soldiers stationed overseas who were missing their families. Because it was released during the height of World War II, the song was well-received in America as a means of capturing a sentiment felt by so many. But the BBC actually banned the song from being played in the U.K., fearing it could lower morale among the troops.

Modern artists have released their own versions of this classic song as well, with versions by Camilla Cabello, Kelly Clarkson, and Josh Groban all climbing the charts.

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“White Christmas,” by Bing Crosby

Crosby’s version of this Irving Berlin song is the world’s best-selling single, selling more than 50 million physical copies worldwide. Berlin originally wrote the song about a traditional holiday setting for the 1942 musical “Holiday Inn.” “White Christmas” won the Academy Award for Best Original Song at the 15th Academy Awards in 1943.

Berlin’s biographer said the songwriter knew he had a hit on his hands. He allegedly told his secretary, “I want you to take down a song I wrote over the weekend. Not only is it the best song I ever wrote, it’s the best song anybody ever wrote.”

Millions of people agree, which is why “White Christmas” has become such an enduring favorite for the season.

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“Christmas Eve/Sarajevo 12/24,” Trans-Siberian Orchestra

This chilling instrumental song for the holiday season doesn’t need any words to convey extreme emotion. The four-part medley of “God Rest Ye Merry, Gentlemen” and “Shchedryk” has distinct highs and lows. It’s about a single cello player playing Christmas carols in Sarajevo during wartime. 

Band member Paul O’Neill explained the background and inspiration for the song in a 2003 interview with Christianity Today. 

“We heard about this cello player [Vedran Smailović] born in Sarajevo many years ago who left when he was fairly young to go on to become a well-respected musician, playing with various symphonies throughout Europe. Many decades later, he returned to Sarajevo as an elderly man—at the height of the Bosnian War, only to find his city in complete ruins,” O’Neill recalled.

“I think what most broke this man’s heart was that the destruction was not done by some outside invader or natural disaster—it was done by his own people,” he continued, saying that instead of going into a bomb shelter to hide, Smailović decided to climb a rubble pile in the town square and play his cello. 

“He came every night and began playing Christmas carols from that same spot. It was just such a powerful image—a white-haired man silhouetted against the cannon fire, playing timeless melodies to both sides of the conflict amid the rubble and devastation of the city he loves,” O’Neill went on. “Some time later, a reporter traced him down to ask why he did this insanely stupid thing. The old man said that it was his way of proving that despite all evidence to the contrary, the spirit of humanity was still alive in that place.”

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