Guest Stars Jerry Adler as Howard Lyman Michael Cerveris as James Castro Jill Hennessy as Rayna Hecht Katie Paxton as Lauren Lytton Tom Skerritt as James Paisley Merwin Goldsmith as Simon Fishbein Joe Holt as Donald Pearl Jacqueline Antaramian as Marcy Economus Jennifer Restivo as PR Consultant Steven Hauck as Fund Manager #2 Sydney James Harcourt as Steven Lewis Anne Lange as Fund Manager Ryan Garbayo as Server