Guest Stars Josh Hamilton as Matt Jensen Steven Weber as Principal Gary Bolan Michele Selene Ang as Courtney Crimsen Joseph C. Phillips as Greg Davis Wilson Cruz as Dennis Vasquez Brian d'Arcy James as Andy Baker Steven Silver as Marcus Cole Sosie Bacon as Skye Miller Maria Dizzia as Mrs. Down Tom Everett Scott as Mr. Down Henry Zaga as Brad Giorgia Whigham as Kat Tom Maden as Robert Wells Co Starring Timothy Granaderos as Montgomery De La Cruz Uncredited London Freeman as Student