Bing Crosby, Frank Sinatra, Brenda Lee, Nat King Cole, and Andy Williams all reside in a common place of eternal prestige. They dominated the holiday music market when your parents were kids, and they still dominate that market today. Their songs soundtrack at least 1/12th of the year, making homes feel cozier and random public venues feel more familiar with the holiday sounds we all grew up with.

Believe it or not, their holiday dominance need not exist. Yes, those artists are legends for a reason. Songs like Rockin’ Around The Christmas Tree, The Christmas Song, and It’s the Most Wonderful Time of Year are, by definition, timeless. But between new seasonal bops like Samara Joy’s “Warm in December“, to genuinely funny new holiday songs like Brave Combo’s “O Holy Night Cha Cha Cha“, to new off-color Christmas jams like MJ Lenderman’s “Rudolph“, there are a wider variety of holiday songs that get wildly underappreciated on a yearly basis. Maybe it’s because they aren’t recognizable. Maybe it’s because they would sounds weird coming through the speakers of your local department store. But think of this playlist as the anti-department store playlist. It’s the playlist your Grandma would cringe at, asking “what is this?!” as she winces at the thought of thick guitar licks and blatant profanity casting a shadow over what she traditionally recognizes as a holiday song. It’s rebellious, fun, weird, and most of all, worth a listen.

The joy I find in creating this playlist every year is hard to describe. I hope it brings you and yours some joy this holiday season too.