Guest Stars Jennifer Jason Leigh as Jill Price-Gray Gavin Kent as Stevie Ethan Kent as Stevie Amanda Pace as Taylor Danièle Watts as Angela Mullen David Julian Hirsh as Rabbi David Bloom Rachel Pace as Shayla Tammy Caplan as Spoons Kevin Sussman as Terry Ben Tolpin as Zachary Craig Anton as Mark Powell Jack Topalian as Pigeon Mike Gloria Laino as Maria Teya Patt as Janet Mary Kathleen Gordon as Joan Hillary Kind as Iris Reggie Baker as Karney Co Starring Jason Kaine as State Regulator Markos Lomeli as Jill's Drug Buyer