25 beloved holiday albums to rediscover this winter

A Jolly Christmas from Frank Sinatra – Frank Sinatra

Before Michael Bublé crooned his way into our hearts during the holiday season, there was good ole Frank Sinatra. He released his first full-length Christmas album way back in 1957 and it remains a classic that gets serious airtime even 60 years later.

A voice like Sinatra’s is perfect for the holiday classics that we all love, so the album was chock full of them: “Jingle Bells”, “The Christmas Song”, “Have Yourself A Merry Little Christmas”, “The First Noel”, and the list goes on and on. Sinatra also recorded two original tracks, “The Christmas Waltz” and “Mistletoe and Holly”. The album has been re-released a million times over the years (I’m exaggerating just a bit), first in 1963 and most recently in 2010 on vinyl for the first time since 1986. Sinatra also released the compilation album Christmas Songs by Sinatra in 1948 as a 78 rpm album set.

I don’t know what it is but there’s something about a crooner singing Christmas standards that really makes it feel like the holiday season. Listening to these tracks will make you feel like you’re a kid again, sitting by the fire drinking hot cocoa as your parents read you The Night Before Christmas before you snuggle into bed waiting for Santa. Even if you weren’t even close to being alive in the 1950s when Sinatra first released the album, or even if you never listened to it growing up, there’s just some quality about it that will always feel nostalgic — for me at least.