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 Stevvi Alexander as Beauty Parlor Woman Emil Beheshti as Cooke Counsel 2 Thom Pinto voices Male Radio Broadcaster Ashley Argota as Horn Nightclub Singer Michael Whaley as Horn Nightclub MC Landon Gordon as Child Actor Courtney Friel voices Female Radio Broadcaster Gayla Johnson as Beauty Parlor Woman Jonathan T. Floyd as Fred / Playboy Mansion Valet Stewart Skelton as Cooke Lead Counsel Tiffany Jeneen as Beauty Parlor Woman Bettye Davis as Funny Johnson Aunt Harold Boons as Funny Johnson Uncle Shiyenne Talley as Johnson Sister Yulia Rogatneva as Sterling Girl Catherine Pearlman as Bulls Secretary Idan Ravin as Daytime TV Actor Theresa Cameron as Stage Mom Michael Majacks as Cab Driver Carmit Bachar as Horn Nightclub Singer Michael James Boehler as Naked Man Melinda Sullivan as Horn Nightclub Singer Brian Mahoney as Sportswriter Anusha Angur as Young Nurse Daniel DeYoung as Rod Thorn 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
