The song dates from 1944, is credited to Hugh Martin and Ralph Blaine for Judy Garland's 1944 movie, Meet Me in St. Louis, but it's generally acknowledged to be Hugh Martin's writing. The somber tone is understandable; Christmas of 1944 was three years into World War II, and many people had undergone the hardship of long separations from or the loss of family members. The war was wearing on the national psyche; the death toll was the highest seen since the Civil War. They were dark days. It's interesting, then, that Martin has said he wasn’t consciously writing about wartime separations.
You'll note that at the end of the song, the line isn't “hang a shining star upon the highest bough”, it's the more subdued “until then, we'll have to muddle through somehow.” Much more fitting to a more somber song written during WWII. The change to “...highest bough” (which seems to be the last) was prompted by Frank Sinatra in 1957. According to Entertainment Weekly in 2007,
Then, in 1957, Frank Sinatra — who'd already cut a lovely version with the movie's bittersweet lyrics in 1947 — came to Martin with a request for yet another pick-me-up. “He called to ask if I would rewrite the 'muddle through somehow' line,” says the songwriter. “He said, 'The name of my album is A Jolly Christmas. Do you think you could jolly up that line for me?' ”That request led to the line we hear most often, although Martin says he thinks the original line is more “down-to-earth.” “Have Yourself a Merry Little Christmas” has become one of the most popular songs year after year. EW says it's second only to the Nat King Cole-popularized “The Christmas Song (Chestnuts Roasting on an Open Fire).” It has been covered by a gamut of artists from Sinatra to Connie Stephens, to James Taylor (who sings something closer to the '40s, Judy Garland version) to '80s metal band Twisted Sister, and many, many more.
I'm not so one-dimensional that this is the only song I can live with for the month, though. When I play them myself, I tend to start by playing “O Holy Night” although I can't hope to get within a light year of this order of ability - or hit that vocal range under any circumstances.
Still, a fingerstyle guitar can approach the sound of the piano in the mix here. I can't really link to a video that sounds like what I attempt to play because I sit with a piano song book and work from that sheet music.
And there are more. If asked to pick my one most favorite Christmas song, as if I could, I'd probably pick one of these two. There are lots that are fun to listen to once or twice a year, even the cliche' “Jingle Bell Rock” is fun a few times. There are fewer that I could listen to lots throughout this month.
What are yours?