one of the staff writers. Simon Stiles (D. L. Hughley), the final member of the "Big Three", became an alumnus of the Yale School of Drama after a troubled youth. His original intention was to become a dramatic actor, rather than a comedian. Jack Rudolph (Steven Weber) is the chairman of the National Broadcasting System, and Jordan's boss. During the course of the show, he and his wife separate. Cal Shanley (Timothy Busfield) is the director of Studio 60. He has two children and is a military history buff. (Busfield also directed several episodes of the series, as he did for Sports Night.) Secondary roles Jeannie Whatley (Ayda Field) is a member of the show's ensemble. She is Matt's occasional lover and Harriet's close friend and is a bit of a gossip on the set. Alex Dwyer (Simon Helberg) is a member of the show's ensemble; he is recognized as the complement to Harriet Hayes, being the premier male impressionist in the cast. He has at least one recurring sketch, The Nicolas Cage Show, in which he plays the title character, and has also portrayed Tom Cruise and Ben Stiller. Dylan Killington (Nate Torrence) is a rookie member of the show's ensemble. Dylan plays a number of different characters in the show-within-a-show. During "Nevada Day Part – II", Simon goes to Nevada with Tom, Danny, and Jack; Matt then asks a reluctant Dylan to fill in for Simon in News 60. He has a crush on Jeannie. Samantha Li (Camille Chen) is a member of the show's ensemble. Ricky Tahoe (Evan Handler) is a former co-executive producer of the show and former co-head of the writers' room. In "The Option Period", he and Ron leave Studio 60 to pursue a pilot show for Fox called Peripheral Vision Man – based on a character from an old Studio 60 sketch; Ricky's departure is marked by a hostile shouting match with Matt. Ron Oswald (Carlos Jacott) is a former co-executive producer of the show and former co-head of the writers' room. In "The Option Period", he leaves the show with Ricky to pursue a pilot show for Fox called Peripheral Vision Man – based on a character from an old Studio 60 sketch. Wilson White (Edward Asner) is the head of TMG (Tunney Media Group), the conglomerate that owns the NBS network. Lucy Kenwright (Lucy Davis) is a junior writer on the