The present article investigates the existence, multiplicity and regularity of weak solutions of problems involving a combination of critical Hartree type nonlinearity along with singular and discontinuous nonlinearity. By applying variational methods and using the notion of generalized gradients for Lipschitz continuous functional, we obtain the existence and the multiplicity of weak solutions for some suitable range of $\lambda$ and $\gamma$. Finally by studying the $L^\infty$-estimates and boundary behavior of weak solutions, we prove their H\"{o}lder and Sobolev regularity.
