I've bought a lot of Christmas records over the past 35 years or so. And while I can't imagine that any record will ever unseat John Fahey's New Possibility or Phil Spector's A Christmas Gift to You from their perennial perch at the top of my stack, there have been a few that have come close over the years, like Kenny Burrell's Have Yourself a Soulful Little Christmas, Jimmy Smith's Christmas '64, or the various packagings of James Brown's Christmas singles.
One such record that has increasingly ingratiated itself into my holiday playlists is Herb Alpert and the Tijuana Brass's Christmas Album, which always sounded good to me when I was spending my Christmases in Southern California, but now sounds even better while watching the snow fall on my chilly Chicago neighborhood. I actually think it's the most underrated Jewish Christmas record ever, so I wrote a piece about it for the Forward, which you can read HERE.
And if you want a little taste of what I'm talking about, here's a great video of Herb and the TJB getting into the holiday act, Hollywood-style: