We explore the connection between the rank of a polynomial and the singularities of its vanishing locus. We first describe the singularity of generic polynomials of fixed rank. We then focus on cubic surfaces. Cubic surfaces with isolated singularities are known to fall into 22 singularity types. We compute the rank of a cubic surface of each singularity type. This enables us to find the possible singular loci of a cubic surface of fixed rank. Finally, we study connections to the Hessian discriminant. We show that a cubic surface with singularities that are not ordinary double points lies on the Hessian discriminant, and that the Hessian discriminant is the closure of the rank six cubic surfaces