The era of cheap and easy streaming music makes it easy for anyone to assemble a pretty nifty playlist for the holidays. However, you need to go beyond just your favorite songs. You need to dive into Christmas albums and build sets that can be spun for hours as the soundtrack for your parties, dinners, and Christmas morning celebrations.

The core of these selections should be built around the holiday music of Frank Sinatra, Bing Crosby, and Dean Martin.1 But to do it right, you need to go beyond those legends. So, as my holiday gift to you, here are some fine albums that should be in the collection (virtual or real) of every discriminating holiday entertainer.

Ella Wishes You a Swingin Christmas – Ella Fitzgerald
Merry Christmas From Lena Horne – Lena Horne
Two albums filled with the lightness of the season and wonderful vocal performances. Fitzgerald is more technically pure where Horne bounces along in a jazzy style. Fitzgerald’s “What Are You Doing New Year’s Eve?” is the perfect song to end the holiday season with.

A Christmas Gift For You From Phil Spector – Various
The Wall of Sound comes to Christmas. The Ronettes, The Crystals, and the greatest pop Christmas song ever.

The Nutcracker Suite – Duke Ellington and His Orchestra.
Jazzy takes on the holiday magic that is The Nutcracker? Yes, please!

Ultra-Lounge/Christmas Cocktails – Various
Christmas Remixed – Holiday Classics Re-Grooved – Various
A fine way to spice up the season with classic tunes by the original performers reimagined through new backing music. The Ultra-Lounge set makes each song sound straight out of 1960s Las Vegas. While Remixed puts the originals over beats crafted by modern DJs. Both albums are fantastic and perfect for the uptempo portion of the night.

The Ultimate Classical Christmas Album Of All Time – Various
And here we find the balance to the swingin’ tunes. Beautiful songs for late in the evening, when the lights are dimmed and you can enjoy one last drink while admiring the tree. Forty-three tracks, so best when trimmed to fit your preferences.

  1. Each offer several fine choices. I recommend A Jolly Christmas From Frank Sinatra, A Merry Christmas with Bing Crosby and the Andrews Sisters, and Deano’s Making Spirits Bright. ↩