Several years ago, during an involuntarily long stretch of unemployment, I partially supplemented my income by buying and selling Sinatra memorabilia, primarily records. During that period of time a good many interesting items passed through my hands. While the collector in me wanted to keep every last one of them for myself, practical matters forced me to part with them. Though I knew a little bit about Sinatra rarities when I started this venture, I knew quite a lot by the time I’d finished and resumed regular employment.

The first thing I learned was the short answer to the question, “What is a rare Sinatra item?” The surprising answer is: not as much as you’d think. And there is a very simple reason for this. As one of the most popular performers of his generation, Sinatra’s recordings, in particular, were mass produced, widely available and many remain to this day in the hands of those who originally purchased them. Due to Sinatra’s popularity, true rarities are hard to find.

But if you know what to look for, there are some clear gems out there where you might least expect them. Over the next several days, I’m going to profile the various categories of memorabilia that are among the hardest to find and most desirable, beginning with what some might consider the Holy Grail of Sinatra recordings.

Stay tuned.