The Best Versions of Classic Christmas Songs

It’s the holiday season, the most wonderful time of the year to hear Christmas classics everywhere you go. Carols are in the air and it doesn’t show signs of stopping. Some Christmas songs do not age well, but there are two dozen or so that stand the test of time.

When Bing Crosby passed away while playing golf in Spain back in 1977, his voice had been beard by more people than any other person in human history, thanks to composer Irv Berlin. Crosby was the star of Hollywood’s first two holiday mega-hits, Holiday Inn and White Christmas, setting the tone for all others to follow.

Over the years some folks have tried their own renditions of Crosby’s classics. Some are the worst thing your ears will ever hear, like Justin Bieber and Busta Rhymes’ Little Drummer Boy, but a few artists may have usurped the ultimate Christmas Crooner.

White Christmas: The Drifters

You can never surpass Bing’s beautiful ballad. When NPR ranked the Top 100 songs of the 20th century, only Judy Garland’s Somewhere over the Rainbow finished higher. An alteration is the only way one can come close and that’s exactly what The Drifters did in 1954. The unique stylings became a staple nearly a half century later when it was featured in Home Alone and The Santa Clause.

Silver Bells: Steve Wonder

Arguably my favorite Christmas artist, this actually isn’t his best work. Like Darlene Love, Stevie’s best carols are originals, like What Christmas Means to Me and Someday at Christmas. An absolutely beautiful song, simply put, this duet takes my breath away.

Santa Claus is Coming to Town: Bruce Springsteen

The Boss is know for his passionate prose. He sings from deep down in his gut, pulling out as many emotions as possible every time he opens his mouth. It’s a Christmas Miracle that he has not killed his vocal cords after doing it for decades. Springsteen pleads with the listener to get ready, providing a sense of urgency that you better get ready for Santa Claus and you better do it as soon as possible.

Little Dummer Boy: Johnny Mathis

Is it even Christmas if you don’t hear some Johnny Mathis? I don’t think so. What makes Mathis so endearing years later is that his voice is actually kind of creepy. His hollow pitch is easily imitated and exaggerated. If you’ve ever watched, Game of Thrones, The Crown or Peaky Blinders, you surely go through a phase where you pick up and start speaking with their accents in casual conversations. The same effect applies every time Mathis comes on the radio around Christmastime.

Do You Hear What I Hear? Whitney Houston

The wonderful thing about the Christmas genre is that it is timeless, yet each song comes with a timestamp. The heavy synth tells you the Eurythmics are Walking in a Winter Wonderland in the late 80s. The music that accompanies Whitney Houston’s timeless voice provides a timestamp from that same era.

Frosty the Snowman: Willie Nelson

If anybody knows a thing or two about corncob pipes, it’s Wille Nelson. Pot jokes aside, the lyrics and singer are a perfect match. Most probably think of the cartoon when they hear Frosty the Snowman, but if you push all that aside, it Frosty sounds like a crazy tall tale that your grandpa would tell by the fire. The folksy sound from Willie was made to accompany the legend of Frosty.

O Holy Night: Celine Dion

You gotta have some serious pipes to pull off this song. She doesn’t meet the listener’s expectations, she blows them completely out of the water.

Hark, The Herald Angels Sing: Carrie Underwood

Country music doesn’t always jive with Christmastime. The genre best fits the Fourth of July. Still, there are some good ones, like George Strait’s Christmas album, Dolly Parton and Kenny Rogers’ Christmas to Remember, and this gentle version produced by Carrie Underwood.

Joy to the World: Aretha Franklin

The ideal, “church is over, let’s celebrate” song, nobody can inject more energy and joy into four and a half minutes than the Queen of Soul accompanied by a raucous choir.

I Saw Mommy Kissing Santa Claus: Jackson Five

There are so many things about this song that will make you laugh and probably not for the right reasons. First off, it starts with an exaggerated smooch that only a music producer from the 70s would think is a good idea. Secondly, the commentary in-between the singing is just golden. “And I’m gonna tell my Dad,” Michael tells his brothers, who promptly call him on his crap. Is it weird in hindsight? Maybe, but is it still amusing? Of course.

Mary, Did You Know? Pentatonix

The five-person a Capella group was made to create holiday hits. Their process is pure wizardry as far as I’m concerned. In addition to the cool sound effects, they are incredibly gifted singers that can hit all the high and low notes. Every single Christmas song they make is wonderful, but this combination is the best of the best.