The answer to this question changes less frequently for most musicians as they evolve and mature. I am no exception. For many years I played whatever sounded “nice”. Being easy to play was another criterion, but that became less of a concern as skills were developed, the main one being finger style picking. Thanks to Frank Wheeler, a pianist who jilted the piano – and his first year Queens University studies – for a guitar, I was introduced to a basic Travis style and a few other techniques, including those required for a passable version of Bert Yanch’s “Angie”. That was a breakthrough that continues today.
It is an embarrassment – maybe only to me – that I was almost oblivious to lyrics for many years, a result of immaturity on many levels. I like to think that I am making up for that flaw; I now follow a very simple rule for choosing songs to play – they must move me emotionally. This recognizes lyrics, universal experience, taste, and, unless there is scope for a very distinctive version of an overplayed song, relative obscurity.
I was unaware of the extent of this process until I resumed serious playing in 2006 after several hiatuses that followed my last full time commitment to music from 1980-85. I immediately jettisoned about one third of the approximately 150 songs from the previous active repertoire. While this felt right, it took longer to realize that this change of heart had been going on while the instruments lay in their cases, and that meaningful expression through any art form – visual, literary, theatrical, or musical – is an accurate reflection of our experience.