Fifties jazz singer Pearl Bailey shows how it's done with "Five Pound Box of Money," the type of Christmas gift that I could really go for. The song's a fun play on the materialism of the holiday, taking it to its logical extreme.
So many performers screw up their Christmas songs by making them radical departures from their normal style, or by trying to sing hoary old holiday standards. It's much more fun when a country singer like Ernest Tubb takes his signature tune, "I'll be Walking the Floor Over You" and turns it into "I'll be Walking the Floor this Christmas."
Speaking of deviating from one's strengths, Elvis' "Blue Christmas" has always left me a little cold. However, his rendition on the '68 comeback special, with Elvis tearing into his guitar and the song while clad in black leather, gives it the kind of rough edge it needed on record.
Not all Christmas songs that get major airplay this time of year necessarily stink. The top 40 station in my hometown played this McKenzie brothers tune every year and I still love it. After all these years SCTV holds up really damn well too, much more so than Saturday Night Live. Don't believe me? Check out this hilarious Christmas moment from the show.