Guest Stars Will Miles as Jay-Mal Rashawn Nadine Scott as Kitty Goodnight Tyla Abercrumbie as Ms. Langford Rolando Boyce as Captain Hedges Cedric Young as Coach Murphy Larry Yando as Wheyland Pace Co Starring Maura Kidwell as Judrith Scottadalehauser Shanessa Sweeney as Mrs. Gurvey Sophie Ackerman as Drama Kid Ricky Falbo as Random Kid #1 Jabari Salahuddin as Lambert Jonah Saesan as Younger Wheyland Jillian Ebanks as Monique Jalen X. Mason as Seamus Phallon Pierce as Kenielle Jeffery Cusic as Raheem Jennifer Joan Taylor as Administrator