Judges on Judging: Views from the Bench

This is a broad survey of many aspects of US court history and judging, assembled from a diverse array of sources, although quite a lot of the authors are contemporary judges. If you have a running interest in the law, this is quite readable even for non-lawyers. Most of the authors are actually remarkably lucid and a pleasure to read. Other volumes that might be of interest for you include Cardozo's "selected writings" (on judging and law; 1920s) and Neumann's book on legal reasoning for law students (or afficionados).