The importance of money in Shaw’s plays needs no introduction, as many of his plays pivot around economic elements. The concrete expression of such elements, however, poses difficulties for many modern audiences/readers who, for example, do not know how the pound sterling was divided before decimalization. Another difficulty arising from the phraseology of money in Shaw’s plays is the fact that inflation is not accounted for. At the same time, Shaw’s prolific and long- lasting playwriting career, together with his personal ascent from a “downstart” to a wealthy, world-class author, create other economic discrepancies between how (much) money is represented in his dramatic canon over different periods—no wonder, given that Shaw produced plays through both world wars, the Belle Époque, and the Great Depression, events that brought about remarkable fluctuations in inflation alone. These two caveats parallel the two main purposes of this article. The first one is to provide a general, chronological guide to the value of money in Shaw’s plays when contrasted with present-day terms; the second is to analyze how historical and personal changes shaped the author’s concept of money and wealth, as expressed in the representation of both in dramatic form.