Guest Stars Jerry Adler as Howard Lyman Michael J. Fox as Louis Canning Michael Cerveris as James Castro David Fonteno as Judge Robert Parks 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 Sydney James Harcourt as Steven Lewis Co Starring Jennifer Restivo as PR Consultant Steven Hauck as Fund Manager #2 Anne Lange as Fund Manager Ryan Garbayo as Server