In 1963, when this album was recorded, overdubbing was still controversial among jazz fans. Some purists held up their hands in horror at the idea of something so artificial as putting one recorded track on top of another - or, as on most of this album, amalgamating three different tracks. Pianist Bill Evans would record one track, then listen to it on headphones while layering another track on top of it - and then a third. The proof of the pudding is in the results: an album which became an immediate classic.
The recordings were made less than two years after bassist Scott La Faro had died, effectively ending one of the pioneering piano trios in jazz. So Conversations with Myself may be regarded as Bill Evans trying to create a new trio from three of his own voices. It is a conversation in that the left channel often seems to converse with the right-hand channel, while the centre channel passes comments on the dialogue. But sometimes it is not so much a conversation as a chance for Bill to add extra layers to his playing. His use of chords was always one of the distinctive qualities of his style, and this project enabled him to build up complex edifices of chords. The different voices seem to merge together or work in harmonious counterpoint with one another.