Tom Mison Ichabod Crane Actor Janina Gavankar Diana Thomas Actor Lyndie Greenwood Jenny Mills Actor Jeremy Davies Malcolm Dreyfuss Actor Rachel Melvin Alex Norwood Actor Jerry MacKinnon Jake Wells Actor Oona Yaffe Molly Thomas Actor Kamar de los Reyes Jobe Guest Star Seychelle Gabriel Lara Guest Star Lionel Fine Geoffrey Guest Star Dheeba Donghrer Parent Guest Star Bailey Tippen Kendra Guest Star Sash Morfaw Classy Guy Guest Star Onye Eme-Akwari Classy Girl Guest Star Hayley Lovitt Bryce Guest Star Edwin Hodge Guest Star Lawrence Kao Guest Star Alex Kurtzman Executive Producer Roberto Orci Executive Producer Len Wiseman Executive Producer Heather Kadin Executive Producer