The subject of diffraction of waves by sharp boundaries has been studied intensively for well over a century, initiated by groundbreaking mathematicians and physicists including Sommerfeld, Macdonald and Poincaré. The significance of such canonical diffraction models, and their analytical solutions, was recognised much more broadly thanks to Keller, who introduced a geometrical theory of diffraction (GTD) in the middle of the last century, and other important mathematicians such as Fock and Babich. This has led to a very wide variety of approaches to be developed in order to tackle such two and three dimensional diffraction problems, with the purpose of obtaining elegant and compact analytic solutions capable of easy numerical evaluation.The purpose of this review article is to showcase the disparate mathematical techniques that have been proposed. For ease of exposition, mathematical brevity, and for the broadest interest to the reader, all approaches are aimed at one canonical model, namely diffraction of a monochromatic scalar plane wave by a two-dimensional wedge with perfect Dirichlet or Neumann boundaries. The first three approaches offered are those most commonly used today in diffraction theory, although not necessarily in the context of wedge diffraction. These are the Sommerfeld–Malyuzhinets method, the Wiener–Hopf technique, and the Kontorovich–Lebedev transform approach. Then follows three less well-known and somewhat novel methods, which would be of interest even to specialists in the field, namely the embedding method, a random walk approach, and the technique of functionally-invariant solutions.Having offered the exact solution of this problem in a variety of forms, a numerical comparison between the exact solution and several powerful approximations such as GTD is performed and critically assessed.