Pretty much every commercial recording artist over the past 60 years or so has produced at least one album of Christmas music. Some are pretty good. Some are pretty terrible. But there are three that stand out for me above all others. They are:
A Jolly Christmas from Frank Sinatra… Frank Sinatra, 1957
This was sort of the one that started it all, Frank’s 1957 effort accompanied by the great Gordon Jenkins and the Ralph Brewer Singers. There’s actually some thought behind the track listing on this one that’s not so obvious on Spotify: Side One of the original record features “popular” Christmas songs such as “Jingle Bells” and “Have Yourself a Merry Little Christmas,” while Side Two contains churchy titles such as “Hark! The Herald Angels Sing” and “Silent Night.” Once again proving his great depth as an artist, Sinatra shines in either setting.
A Charlie Brown Christmas… Vince Guaraldi Trio, 1965
This is the album that accompanies the TV special, which features little snippets of Vince and his trio. Completely synonymous with Christmastime, no album conveys the joy and playfulness of the holidays while giving hints to its seriousness as well.
A Swingin’ Christmas… Tony Bennett with the Count Basie Big Band, 2008
Forty years after Tony Bennett recorded his first Christmas album he returned to the studio to do it again, producing a record even better than his first. Proof that at 82, the guy could still swing. Backed on some tracks by his jazz quartet and on others by the Count Basie Big Band (if you can pull that off you can swing), Christmas has never swung better.