Guest Stars Sean Patrick Small as Larry Bird Michael Chiklis as Red Auerbach LisaGay Hamilton as Christine Johnson Wood Harris as Spencer Haywood Rickey Eugene Brown as Quincy Johnson Darone Okolie as Larry Johnson Steve Harris as Dr. Thomas Day Donnell Rawlings as Mr. Earl Chelsea Marie Davis as Rhonda Mitchell Orlando Jones as Elgin Baylor Co Starring Michael Boucher as Jack Curran Newton Mayenge as Jim Chones Max E. Williams as Jack Nicholson Chris Doubek as Reporter David Bowe as Reporter Timothy E. Goodwin as Reporter Shelby Moats as Marty Byrnes Ian Boyd as Leon Riley Annelisha Dixon as Yvonne Johnson G. Larry Butler as Johnny Most Mike Scott as Butch Lee Christopher Gehrman as Bill Fitch Edward Fletcher as Sportswriter Ted Enberg as Dick Enberg Christien Heath as Lead Official Sean Grant as Traveling Press Tom Antonellis as Boston Driver Amos Glick as Various Media Tom Cunningham as Traveling Press Stephen O'Mahoney as Various Media Roy Abramsohn as Lansing Anchorman Chuck Lacey as Gahden Ushah John Deignan as Sportswriter Katherine Taylor as Female Fan Jazlyn Nicolette Sward as Groupie Rachel Braff as Stewardess