Jenji Kohan Creator, Executive Producer Mary-Louise Parker Nancy Botwin Actor Elizabeth Perkins Celia Hodes Actor Kevin Nealon Doug Wilson Actor Tonye Patano Heylia James Actor Romany Malco Conrad Shepard Actor Hunter Parrish Silas Botwin Guest Star Alexander Gould Shane Botwin Guest Star Andy Milder Dean Hodes Guest Star Renee Victor Lupita Guest Star Allie Grant Isabelle Hodes Guest Star Indigo Vaneeta Guest Star Shoshannah Stern Megan Guest Star Jesse Head Caleb Guest Star Tressa DiFiglia Maggie Guest Star Shawn Schepps Alison Guest Star Becky Thyre Pam Guest Star Craig X. Rubin Craig X Guest Star Kathleen M. Darcy Teacher Guest Star Devon Gearhart Billy - Kid Guest Star Jina Song Reporter Guest Star Joey Capone Skateboard Kid Guest Star Roberto Benabib Writer Craig Zisk Director