Frank Sinatra – “Jingle Bells” – (1957)

Let’s be honest, “Jingle Bells” is a kids song. But nobody does it better than Frank. I love the “I love those J-I-N-G-L-E bells.” And then Sinatra comes in singing – you can almost hear the scotch in his hand sloshing around as he sings this one. The background vocals are great too. This is one of my favorite Christmas songs. It just came from that perfect time (the 1950s) for music like this. For me, picturing a “traditional” Christmas scene almost always ends up as a snowy 1950s American scene. With a song like this playing in the background.

#18 – Bobby Helms – “Jingle Bell Rock” – (1957)

Easily the best rockabilly Christmas song. While rock artists (such as The Eagles, Bruce Springsteen, and even Lynyrd Skynyrd) have had success releasing Christmas music, there are very few successful rock-styled Christmas songs. That’s one reason that Bobby Helms’ classic has enjoyed air-play for the last 50 years: it’s unique. Other “jingle bell” related Christmas songs include Frank Sinatra’s excellent 1957 version of “Jingle Bells.” It is, perhaps, the most “50s” styled song I’ve ever heard. It’s so easy to picture Sinatra swaying around on stage with a glass of whiskey in one hand and a microphone in the other.