I can’t hold an eggnog-scented candle to NR’s resident Christmas-carol crooner and musical-history expert, Mark Steyn, but quite a few readers liked this section of today’s Jolt:

Christmas Season: When the 1940s and 1950s Suddenly Return with a Vengeance
After yesterday’s tart rebuke of those who pooh-pooh complaints about a ‘War on Christmas,’ time for something a bit softer.
Americans live in a culture that is youth-obsessed, relentlessly excited and hyping what’s new and different, touting the latest and greatest. Hang around too long, and you’ve jumped the shark.
And yet, sometime in December, suddenly we embrace tradition as if to make up for the preceding eleven months. Go to a coffee shop or your local department store, suddenly the air is filled with the voices of the pop stars your parents and grandparents listened to: Frank Sinatra, Dean Martin, Judy Garland, Perry Como, Bing Crosby, Nat King Cole, Burl Ives, Glen Campbell, Mel Tormé.
Every era contributes at least a few songs to the ever-growing Christmas canon, but World War II and the postwar years were an amazing span of creativity for carol-writers and performers. It’s probably close to impossible to find a Christmas album that doesn’t include at least one song from this era: “White Christmas,” 1942; “Have Yourself a Merry Little Christmas,” 1943; The Christmas Song” (better known as “Chestnuts Roasting on an Open Fire”), 1944; “Let It Snow,” 1945; “Sleigh Ride,” 1948; “Rudolph the Red-Nosed Reindeer,” 1948; “Frosty the Snowman,” 1950; “Silver Bells,” 1951; “It’s Beginning to Look a Lot Like Christmas,” 1951; “Little Drummer Boy,” 1957.
A large chunk of VH1’s list of “Best Modern Day Christmas Songs” is in fact modern singers’ versions of tunes from this era.
It’s not that surprising that some of the most classic Christmas songs, specials, etc. came out of the post–World War II era. Nothing like a national near-death experience to make you appreciate everything you have, and how lucky you are if you have your friends and family with you.
I think one of the most wonderfully jarring lyrics of all time comes in “Have Yourself a Merry Little Christmas,” with its brief acknowledgement of our mortality, and the sheer unpredictability of life, and the possibility of losing someone:
Once again as in olden days Happy golden days of yore Faithful friends who are dear to us Will be near to us once more Someday soon, we all will be together If the Fates allow Until then, we’ll have to muddle through somehow So have yourself a merry little Christmas now.
Wikipedia’s entry for the song says the lyric was originally, “through the years, we all will be together if the Lord allows.”
A lot of our big Christmas traditions started in this era. NORAD’s tracking of Santa began in 1955 after a Colorado Springs newspaper ad encouraged kids to call Santa — but then accidentally printed a number at NORAD. How the Grinch Stole Christmas was published in 1957 and turned into a television special in 1966. The stop-motion animation Rudolph the Red-Nosed Reindeer first aired in 1964. The Peanuts Christmas special came along in 1965. Two of the all-time Christmas classics came out right after the war: It’s a Wonderful Life (1946) and Miracle on 34th Street (1947).
There are personal near-death experiences and national ones, and if you survive one, hopefully it makes you cherish all the joys in life — to not take anything or anyone for granted, and not to get too wrapped up in any of the things that don’t matter quite so much — even finding that perfect gift or getting everything just right for the party.
Here we are, fifty years later, and we’re still singing songs from that era, because that sentiment of appreciating what matters most still resonates when the year comes to a close.

The cartoonist XKCD suggests the popularity of songs from the 1940s and 1950s represents Baby Boomer nostalgia, and undoubtedly that’s a factor. But the fact that post-Boomer modern artists keep using these songs on their own Christmas albums suggests they have timeless quality. They’re just good songs, and the theme of appreciation and gratitude probably resonates with many as they take stock of their lives as the year ends.