From Sinatra! The Song Is You: A Singer's Art by Will Friedwald:
Old-fashionedness was exactly what Sinatra and Voyle Gilmore (Sinatra's Capitol Records producer) were looking for when they assigned Jenkins the task of orchestrating A Jolly Christmas with Frank Sinatra. The twelve tracks on this seasonal set fairly hang from the chimney with simplicity. That's because Jenkins has chosen to wait before letting his cat of high, moaning strings out of his Santa sack. "I'll Be Home for Christmas" contains the sole discernible glimmer of the patented Jenkins string sound, and even there it's audible only for a brief instrumental passage.
Intriguingly, the most distinctive chart is the least Jenkinsy of them all: the opening "Jingle Bells" commences with the chorus cooing a jivey "Rag Mop" version of the ancient tune, over which Sinatra swings lightly and politely.
Whether he's tossing off references to "baby" or "Jack" with Billy May or ever so sincerely intoning "Merry Christmas" at the end of Sammy Cahn's "Christmas Waltz," Sinatra is never less than convincing. He even seems to have talked himself into believing that it was really Christmas--after the third and final date. Sinatra traded in his "ring-a-ding ding" for a "ho! ho! ho!" when he threw a Christmas party for the musicians, chorus, and engineers in the middle of July. (pp. 337, 338)
My two cents worth and humble onion is, even I, a committed Sinatra-phile, have a difficult time taking him seriously on several of these. It's particularly hard to accept him singing some of the more "sacred," almost hymn-like, things such as "Silent Night," "Adeste Fidles," or "Oh Little Town of Bethlehem," especially knowing as much about his private life and personal philosophy as I do. But, I absolutely adore a few of them, particularly "Mistletoe and Holly" and especially "The Christmas Waltz" (man, that's pretty). Enjoy:
Merry Christmas, Merry Christmas
may your every New Year dream come true!