Five holiday songs to get you into the winter mood

Few things help bring in the holiday season like the waves of music that come along with it. In celebration of that music, here’s my top ten holiday songs, a variety pack of artists and genres. This list will focus on songs actually about the holiday season as we know it now, instead of the variety of fantastic more-religious songs that are out there, with a focus on winter and modern Christmas celebrations. 

I’ll Be Home For Christmas - Frank Sinatra

Cover of A Jolly Christmas from Frank Sinatra, Capital Records

Originally released on A Jolly Christmas from Frank Sinatra in 1957, “I’ll Be Home For Christmas,” is one of ‘Ol Blue Eyes essential songs, winter or otherwise. One of the many tracks that helped that album go platinum, 

“I’ll Be Home For Christmas” stands out the most to me because of how Sinatra manages to make it both a celebration of Christmas and a contemplation of the stresses of life. When we hear him forecasting his return home, there’s a sense that he’s not only in need of a break from his day to day, but that he’s not sure he’ll even actually make it. It’s a somber song, but one that doesn’t stray too far away from the uplifting nature of its lyrics.

White Christmas - Bing Crosby

Performed countless times by Crosby over his career, “White Christmas” may well be the diamond on the crown of the crooner era of holiday music. It’s been covered by just about anyone you can imagine, but Crosby’s cover of the Irving Berlin song tops them all. 

“White Christmas,” as performed by Crosby, is a fantastic combination of happy, somber, and celebratory moods. Crosby misses the christmases of his childhood, but that doesn’t mean the winters of his adult life have to be so bad. It’s uplifting, nostalgic, and touching. It’s a Christmas classic.

Let It Snow! Let It Snow! Let It Snow! - Frank Sinatra/Dean Martin/Boyz II Men/etc

Cover of Christmas Interpretations, courtesy of Motown Records

“Let It Snow! Let It Snow! Let It Snow!” is one of those timeless songs that’s likely destined to kick off winter for as long as there’s music. I’ve chosen not to pick one performer because it’s also a song that’s been covered by so many in multiple ways that frankly it’s impossible to determine. If you want a classic style, the likes of Sinatra or Martin work well. But they’re far from your only options. Penatonix, Boyz II Men, Kacey Musgraves, and Gwen Stefani have all put their own twist on the song.

“Let It Snow! Let It Snow! Let It Snow!” may be a Christmas song, but it’s far more about winter. You’ll struggle to find a better feel good song about the coldest season. Let It Snow keeps it simple, fun, and approachable. The song’s creators, Sammy Cahn and Jule Styne, knew what they were doing with this one.

Silver Bells - Dean Martin

Dean Martin brings a casual energy to all his work, perhaps the trait that makes him stand out most against the clean cut performances and precision of Frank Sinatra. “Silver Bells” is one the best of Martin’s casual performances, combining the tone of “You’re Nobody Till Somebody Loves You” with the holiday cheer of the Crosby Christmas classics.

It’s still a moody song like many of its time, but it’s more like the somber mood after a fun night, rather than that of someone remembering the past. Martin may find himself left out of some lists of the greats, but his contribution to the holiday catalogue is utterly unmissable. “Silver Bells” is the peak of that chapter in Martin’s long career.

Last Christmas - Wham!

Cover of the “Last Christmas” single, courtesy of Columbia

This is a personal favorite, but one that truly deserves wider appreciation. While Wham! is far from a band associated with Christmas songs, their small journey into the genre produced a perfect combination of holiday and break up moods. It’s way poppier than the 50’s Christmas music you’ll usually hear, but it’s also far more emotional than most pop holiday music ever dares to be.

“Last Christmas” is holiday music at its poppy best, combining the intensely 80’s style of Wham! with a somewhat classy and somber observation of winter woes. If you’re not sure where to go for holiday songs between the classics and modern interpretations, “Last Christmas” is a must.