The generalized inviscid Proudman-Johnson equation serves as a model for n-dimensional incompressible Euler flow, gas dynamics, high-frequency waves in shallow waters, and orientation of waves in a massive director field of a nematic liquid crystal. Furthermore, the equation also serves as a tool for studying the role that the natural fluid processes of convection and stretching play in the formation of spontaneous singularities, or of their absence. In this work, we study blow-up, and blow-up properties, in solutions to the generalized, inviscid Proudman-Johnson equation endowed with periodic or Dirichlet boundary conditions. More particularly,regularity of solutions in an Lp setting will be measured via a direct approach which involves the derivation of representation formulae for solutions to the problem. For a real parameter lambda, several classes of initial data are considered. These include the class of smooth functions with either zero or nonzero mean, a family of piecewise constant functions, and a large class of initial data with a bounded derivative that is, at least, continuous almost everywhere and satisfies Holder-type estimates near particular locations in the domain. Amongst other results, our analysis will indicate that for appropriate values of the parameter, the curvature of the data in a neighborhood of these locations is responsible for an eventual breakdown of solutions, or their persistence for all time. Additionally, we will establish a nontrivial connection between the qualitative properties of L-infinity blow-up in ux, and its Lp regularity. Finally, for smooth and non-smooth initial data, a special emphasis is made on the study of regularity of stagnation point-form solutions to the two and three dimensional incompressible Euler equations subject to periodic or Dirichlet boundary conditions.