The soothing voice of Karen Carpenter is heartwarming, clear, and beautiful all at once. Karen and her brother, Richard Carpenter, mastered the art of performing Christmas songs, albeit largely classic ones, that have broad generational appeal. Their music is easily recognizable to the ear as the duo's subdued enthusiasm - evident in their songs - has strong resonance with many Americans who celebrate Christmas. Their songs have earned permanent stay status on radio Christmas playlists precisely because they are so freaking good: pure and simple. "Christmas was meant for Karen Carpenter to sing about," Rolling Stone aptly wrote in a ranking of best Christmas albums. The Carpenters offer the best renditions of "Sleigh Ride" and "Do You Hear What I Hear?" I've ever heard. These two songs in particular are reflective of the smoothness and crispness with which the Carpenters deliver their Christmas music. Their collection of Christmas songs are, by far and away, the best - ever.
2. BING CROSBY
Authoritative, classy, and majestic, Bing Crosby's voice lent itself to a Christmas collection that is worthy of its status as a cultural mainstay. Is there anyone else who could pull off such a wonderful rendition of "White Christmas"? The magic is in Crosby's deep voice which sounds like it could belong to the quintessential family patriarch at the head of a Christmas Eve dinner table anywhere in the United States. Importantly too, Crosby gave us this gem with David Bowie and for this masterpiece alone, he deserves a high ranking on lists such as this one.
3. FRANK SINATRA
Frank gives us a wealth of Christmas songs in which he delivers with signature snappiness and a mellow but pensive, reflective voice that pleases many listeners' sensibilities. Sinatra has especially strong performances of "The Christmas Waltz" and "Santa Claus is Coming to Town." In these songs in particular, Sinatra shines as a contemplative yet joyous style is purely on full display. He's the life of the party but, at the same time, incredibly low-key. That's what makes his Christmas music special.
4. MICHAEL BUBLE
Michael Buble's calm, brisk, and suave voice makes for an impeccable album, released in my freshman year of college at the perfect time: when I was somewhat homesick but reinvigorated at GW by the then-upcoming Christmas holiday. Buble's rendition of "Christmas (Baby Please Come Home)" is especially exciting, energetic, and enthusiastic. His Christmas music perfectly reflects the coexistence in his life of a fun-loving spirit with ostensible classiness. Though released relatively recently in 2011, Buble's Christmas album has merited its rightful place in radio holiday playlists for decades to come.
5. A CHARLIE BROWN CHRISTMAS
The Charlie Brown collection just really makes you feel at home. The tranquil, delightful melodies are brilliantly composed and pristinely peaceful and polished. This is the kind of stuff that kids waking up to Christmas morning ought to be listening to as they race down the stairs to open presents under the tree. Is there anything bad to say about this? I think not. So, I am sure my readers will complain about why it is last place here.
HONORABLE MENTION: Harry Connick, Jr.'s "When My Heart Finds Christmas"
I included this song maybe only because I love the line, "in my eyes are Valentines and Easter eggs and New Year's wine, but when my heart finds Christmas, my eyes will shine like new." Harry Connick, Jr. managed to do a really bang up job of magically incorporating various holidays into a (seemingly increasingly popular) soothing Christmas song. The song is wonderful because it resonates well a sort of childish innocence from an authoritative-looking fella like Harry Connick, Jr.
UPDATE ON 12/23/16: Shame on me for not including Andy Williams with his beaming, magnificent voice that literally lifts your spirits, especially in his thunderous hit, "It's the Most Wonderful Time of the Year."
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