Guest Stars Sean Patrick Small as Larry Bird Michael Chiklis as Red Auerbach LisaGay Hamilton as Christine Johnson Rickey Eugene Brown as Quincy Johnson David Purdham as Larry O'Brien Kate Arrington as Joann Mueller Michael O'Keefe as Jack Kent Cooke Kirk Bovill as Donald Sterling Co Starring Andy Hirsch as David Stern Darone Okolie as Larry Johnson Cayden K. Williams as 8-Year-Old Earvin G. Larry Butler as Johnny Most Ted Enberg as Dick Enberg Edward Fletcher as Sportswriter Ashley Argota as Horn Nightclub Singer Emil Beheshti as Cooke Counsel 2 Michael Whaley as Horn Nightclub MC Stevvi Alexander as Beauty Parlor Woman Jonathan T. Floyd as Fred / Playboy Mansion Valet Tiffany Jeneen as Beauty Parlor Woman Stewart Skelton as Cooke Lead Counsel Courtney Friel voices Female Radio Broadcaster Gayla Johnson as Beauty Parlor Woman Landon Gordon as Child Actor Brian Mahoney as Sportswriter Michael James Boehler as Naked Man Michael Majacks as Cab Driver Theresa Cameron as Stage Mom Yulia Rogatneva as Sterling Girl Harold Boons as Funny Johnson Uncle Bettye Davis as Funny Johnson Aunt Shiyenne Talley as Johnson Sister Catherine Pearlman as Bulls Secretary Melinda Sullivan as Horn Nightclub Singer Idan Ravin as Daytime TV Actor Carmit Bachar as Horn Nightclub Singer Anusha Angur as Young Nurse Daniel DeYoung as Rod Thorn Thom Pinto voices Male Radio Broadcaster Noa Neve as Horn Nightclub Singer Kelly Hansen as Playmate Jeff Pearlman as Journalist Olivia Leigh Nowak as Sterling Girl Nicholas Britell as Horn Nightclub Piano Player Jerry Zucker as Himself David Zucker as Himself Jim Abrahams as Himself Terrence Stone as Butler Emily Berry as Head Nurse Arielle Reitsma as Honey