"Have Yourself a Merry Little Christmas"

Frank Sinatra

Let's be clear: Sinatra could make a Jessica Simpson song sound cool. The man had a voice like a stiff drink. There's just something undeniably masculine about Frankie, and that's why his music must be included on any list of the cool Christmas carols. The Chairman of the Board recorded a ton of Christmas music, and so we could have chosen any number of classic Frank Sinatra Christmas carols, but we've settled on "Have Yourself a Merry Little Christmas" because it's a great example of the velvety smooth vocals that made Sinatra so decisively cool.

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