A concrete description of Hochschild cohomology is the first step toward exploring associative deformations of algebras. In this dissertation, deformation theory, geometry, combinatorics, invariant theory, representation theory, and homological algebra merge in an investigation of Hochschild cohomology of skew group algebras arising from complex reflection groups. Given a linear action of a finite group on a finite dimensional vector space, the skew group algebra under consideration is the semi-direct product of the group with a polynomial ring on the vector space. Each representation of a group defines a different skew group algebra, which may have its own interesting deformations. In this work, we explicitly describe all graded Hecke algebras arising as deformations of the skew group algebra of any finite group acting by the regular representation. We then focus on rank two exceptional complex reflection groups acting by any irreducible representation. We consider in-depth the reflection representation and a nonfaithful rotation representation. Alongside our study of cohomology for the rotation representation, we develop techniques valid for arbitrary finite groups acting by a representation with a central kernel. Additionally, we consider combinatorial questions about reflection length and codimension orderings on complex reflection groups. We give algorithms using character theory to compute reflection length, atoms, and poset relations. Using a mixture of theory, explicit examples, and calculations using the software GAP, we show that Coxeter groups and the infinite family G(m,1,n) are the only irreducible complex reflection groups for which the reflection length and codimension orders coincide. We describe the atoms in the codimension order for the groups G(m,p,n). For arbitrary finite groups, we show that the codimension atoms are contained in the support of every generating set for cohomology, thus yielding information about the degrees of generators for cohomology.