Guest Stars Timothy Granaderos as Montgomery De La Cruz Josh Hamilton as Matt Jensen Mark Pellegrino as Officer Bill Standall Steven Weber as Principal Gary Bolan Michele Selene Ang as Courtney Crimsen Bryce Cass as Cyrus RJ Brown as Caleb Joseph C. Phillips as Greg Davis Anne Winters as Chlöe Rice Wilson Cruz as Dennis Vasquez Tommy Dorfman as Ryan Shaver Chelsea Alden as Mackenzie Samantha Logan as Nina Jones Allison Miller as Sonya Struhl Meredith Monroe as Carolyn Standall Tom Everett Scott as Mr. Down Maria Dizzia as Mrs. Down Andrea Roth as Noelle Davis Ben Lawson as Coach Rick Wlodimierz Kimiko Gelman as Vice Principal Jane Child Jeffrey Vincent Parise as Will Walker Co Starring Brandon Butler as Scott Reed Joey Chacho as Ramón Ordoñez Spence Moore II as Michael Phil Austin as Warren Hank Greenspan as Young Justin Ronan Carroll as Young Bryce