Guest Stars Timothy Granaderos as Montgomery De La Cruz Mark Pellegrino as Officer Bill Standall Steven Weber as Principal Gary Bolan Joseph C. Phillips as Greg Davis Anne Winters as Chlöe Rice Wilson Cruz as Dennis Vasquez Tommy Dorfman as Ryan Shaver Samantha Logan as Nina Jones Allison Miller as Sonya Struhl Sosie Bacon as Skye Miller Meredith Monroe as Carolyn Standall Kelli O'Hara as Jackie Maria Dizzia as Mrs. Down Tom Everett Scott as Mr. Down Jake Weber as Barry Walker Ben Lawson as Coach Rick Wlodimierz Co Starring Brandon Butler as Scott Reed Richard Gross as Judge Campbell Joey Chacho as Ramón Ordoñez Phil Austin as Warren Mikiko Edwards as Cheerleader #1 Callan Taylor as Cheerleader #2 Austin Green as Hipster Artist