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 Mary Kathleen Gordon as Joan Gloria Laino as Maria Hillary Kind as Iris Reggie Baker as Karney Teya Patt as Janet Co Starring Jason Kaine as State Regulator Markos Lomeli as Jill's Drug Buyer