We consider the analytic structure of interfaces in several families of steady and unsteady two-dimensional Stokes flows, focusing on the formation of corners and cusps. Previous experimental and theoretical studies have suggested that, without surface tension, the interfaces spontaneously develop such singular points. We investigate whether and how corners and cusps actually develop in a time-dependent flow, and assess the stability of stationary cusped shapes predicted by previous authors. The motion of the interfaces is computed with high resolution using a boundary integral method for three families of flows. In the case of a bubble that is subjected to the family of straining flows devised by Antanovskii, we find that a stationary cusped shape is not likely to occur as the asymptotic limit of a transient deformation. Instead, the pointed ends of the bubble disintegrate in a process that is reminiscent of tip streaming. In the case of the flow due to an array of point-source dipoles immersed beneath a free surface, which is the periodic version of a flow proposed by Jeong & Moffatt, we find evidence that a cusped shape indeed arises as the result of a transient deformation. In the third part of the numerical study, we show that, under certain conditions, the free surface of a liquid film that is levelling under the action of gravity on a horizontal or slightly inclined surface develops an evolving corner or cusp. In certain cases, the film engulfs a small air bubble of ambient fluid to obtain a composite shape. The structure of a corner or a cusp in an unsteady flow does not have a unique shape, as it does at steady state. In all cases, a small amount of surface tension is able to prevent the formation of a singularity, but replacing the inviscid gas with a viscous liquid does not have a smoothing effect. The ability of the thin-film lubrication equation to produce mathematical singularities at the free surface of a levelling film is also discussed.