Pointer analysis is a critical compiler analysis used to disambiguate the indirect memory references that result from the use of pointers and pointer-based data structures. A conventional pointer analysis deduces for every pair of pointers, at any program point, whether a points-to relation between them (i) definitely exists, (ii) definitely does not exist, or (iii) maybe exists. Many compiler optimizations rely on accurate pointer analysis, and to ensure correctness cannot optimize in the maybe case. In contrast, recently-proposed speculative optimizations can aggressively exploit the maybe case, especially if the likelihood that two pointers alias could be quantified. This dissertation proposes a Probabilistic Pointer Analysis (PPA) algorithm that statically predicts the probability of each points-to relation at every program point. Building on simple control-flow edge profiling, the analysis is both one-level context and flow sensitive---yet can still scale to large programs.