23 years ago, preparing for what I did not know then would be the first in an annual series of holiday music marathons, my teenaged plans were two-fold: 

• Stay on the air as long as I could or until the next DJ showed in the morning.
• Play all the Christmas records in 103.3 fm WPRB’s meager collection alongside the lonnnnnnnnnngest songs I knew (Hello, “Sister Ray!” How have you been, “Marquee Moon”?).

Over two decades later, those Tiny Tim-style crutches are no longer necessary, and I’m allowed to be considerably selective as to what songs end up a part of that year’s marathon playlist.

While I have personal favorites, I try and defer to the listening audience, airing what they want to hear when they want to hear it. In a 24 hour program with no repeats, it is good to always have second and third versions of songs available when people miss their favorites.

There are certain callers I reserve songs for until they phone up to ask for them. They’ve earned it.

Every year I look back on the playlist and can’t believe how many amazing numbers I was unable to fit into the show. That’s part of the fun of doing the show live without a scripted playlist to follow. Needing “only” around 300 songs to work with, a lot of great sounds end up on the sidelines until the next December.

My philosophy for the show has remained the same for as long as I’ve had more than enough quality music to fill the entire program: Play songs that are great songs which just happen to be Christmas songs and try to artfully segue the strange, the fascinating, the beautiful and the alarming around them in a way that keeps the listeners interested but not completely off guard. 

Simultaneously, make sure to pace yourself so the show isn’t too front-loaded or back-loaded with the best of the best. The listener in the middle of the night on the east coast should have the same experience with the program (more or less) as someone in a foreign port of call.

That being said, there are some pieces which make more sense in the middle of the night than at the break of dawn.

Lastly, don’t be satisfied with what you’ve already heard. Even if only a small percentage of it might crack the next year’s show, always be previewing new and newly found holiday songs for something incredible that you and your listeners haven’t heard before.