39. "Let It Snow! Let It Snow! Let It Snow!" Dean MartinFrom the album "A Winter Romance," Capitol (S)T-1285
Recorded August 6, 1959, Hollywood, CA
It's not actually a Christmas song at all, this swingin' Sammy Cahn number about bundling up with your snow bunny of choice when the weather gets too rough. But it's been around now for a half-century in so many versions -- from Vaughn Monroe's 1946 original to Jessica Simpson's recent travesty -- that it seems like a holiday classic, even to those of us from warmer climes. And who better to issue such a seductive, martini-hour version of the offer than the swingingest member of the Rat Pack? Sure, "Baby, It's Cold Outside" works almost as well, but you need two to really pull that off... besides, that seems more like an emotional tug of war than this friendly (but maybe not so innocent) observation.