Guest Stars Jane Adams as Annabelle Jones Marc Maron as Jacob Malco Alexandra Marzella as Alexandra King Bach as Andrew Emily Ratajkowski as Alison Lizowska David Pasquesi as Dave Co Starring Mike Brune as City Lit Employee Spencer Parsons as Spencer Toya Turner as Café Server Chris Ware as Journalist Orion Lay-Sleeper as Big Fan Ryan Andrews as Bartender Justin Kozerow as Justin Ivan Albertson as Ivan Paul Barile as Caroler #4 Kun Cheong as Caroler #1 Nancy Romo as Boltwood Server Angie Mead as Angie Niala Boodhoo as Radio Host Harrison Atkins as City Lit Audience Member Megan Hovany as City Lit Audience Member Pamela Jones as Caroler #2 Kelly Craig as Caroler #3