When you’re feeling nostalgic
If you’re like us, you grew up watching A Charlie Brown Christmas every year. Nothing quite captures that childlike spirit of the holidays like the opening strains of “Christmas Time Is Here,” so when you’re with friends and feeling nostalgic for that Christmas magic of your youth, enjoy jazz great Vince Guaraldi’s classic holiday album.
Warning: It is quite short, and some of the tracks repeat, so use sparingly. The most iconic tracks make great additions to a longer holiday playlist.
When you’re with family
We’ve got a couple of choices that will serve you well, depending on whether you’re more of a Rat Pack fan or prefer Crosby’s velvet tones. Together, these albums will pretty much have you covered as far as the great Christmas classics that everyone in your family will know and enjoy.
Warning: Be prepared for sing-alongs after a few glasses of eggnog.
When you bring that hip lady back to your loft
Sometimes you want a more modern take on the classics. These chillout mixes of traditional carols and classic Christmas songs are perfect for relaxing with a cup of hot cocoa (or a great Scotch) while you show off the view from under the mistletoe.
Warning: Don’t bust this one out around traditionalists; it does have a little bit of a “swanky café” vibe that could come off as pretentious.
When you want background music that won’t make you scream
Your favorite classical Christmas music album
These are the holiday pieces that have stood the test of time, and nothing combines festivity with calmness better than classical music. We recommend Christmas Goes Baroque or, if you want something a little more in-your-face, A Festival of Carols in Brass. Look for albums put out by an orchestra or choir rather than compilations from unknowns.
Warning: It can sometimes be difficult to find all your favorite carols on one album with no obscure pieces. Buy only the tracks you like for your ultimate holiday playlist.
When you want to screw with your friends
You may think this goes against all our previous advice, and sure, it does. But there are times when a healthy dose of trolling is just what the situation calls for. At a friend’s holiday party, smuggle this in, sidle up to the stereo and count the seconds before someone asks, “What the hell is this?” Hey, at least it has a beat you can dance to.
Warning: It’s not as bad as, say, The Jingle Cats, but be careful if you find yourself humming “What Christmas Means to Me” in public.