Guest Stars Sarah Ramos as Cheryl Pistono Sean Patrick Small as Larry Bird Ari Graynor as Honey Kaplan Matthew Barnes as Mitch Kupchak Joel Allen as Kurt Rambis Susan Pourfar as Cassie Westhead Edwin Lee Gibson as Bill Russell Lexi Simonsen as Monica Westhead Co Starring Michael Boucher as Jack Curran Eric Nenninger as Keith Erickson Bailey Swift as Laker Girl David Bowe as Reporter Chris Doubek as Reporter Steve Hartman voices Sports Radio Broadcaster Timothy E. Goodwin as Reporter Andrew Stephens as Kevin McHale Darryl Reynolds as Robert Parish Larry Fields III as Eddie Jordan David Pingalore voices Sports Radio Broadcaster Ian Boyd as Leon Riley Andrea Bess as Laker Girl Katelyn Kushing as Laker Girl Emily Sarah Crouch as Laker Girl Steven Pritchard as Mike Thibault Taylor Dean as Laker Girl Jayne Entwistle as Mary Lou Lieblich Jyn Gittens as Jim Brewer Jacob Liszt as Young Patrick Riley Rachel Rosenbloom as Sports Reporter Emil Beheshti as Sports Reporter Jeff Pearlman as Himself Nicole Appleby as Glendale Woman Chaz Ingram as Sports Reporter Dean Simone as Jim Murray Peter Falls as Dick Stockton Nolan Pugh as Hamlet Waiter Andrew Oliveri as Sports Reporter Don Dowe as Sports Reporter Mark Sande as Beverly Hills Man