Larry David Self, Executive Producer Cheryl Hines Cheryl David Actor Jeff Garlin Jeff Greene Actor, Executive Producer Hugh Hefner Himself Guest Star Gary Player Himself Guest Star Richard Kind Cousin Andy Guest Star Shelley Berman Nat David Guest Star Trisha Debski Social Worker Guest Star Bobbi Sue Luther Playmate Guest Star Holly Madison Herself Guest Star Bridget Marquardt Herself Guest Star James Pickens Jr. Doctor Guest Star Grant Rosenmeyer Wilson Guest Star Bill Saluga Louis Lewis Guest Star Kendra Wilkinson Herself Guest Star Gavin Polone Executive Producer