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 Trishauna Clarke as Debbie Allen Jay Mohr as Tom Collins Co Starring Michael Boucher as Jack Curran Eric Nenninger as Keith Erickson David Bowe as Reporter Darryl Reynolds as Robert Parish Andrew Stephens as Kevin McHale Larry Fields III as Eddie Jordan G. Larry Butler as Johnny Most Toshi Toda as Setsuo Jay Davis as Byron Scott Quentin Shropshire as James Worthy Omari Johnson as Bob McAdoo Jeff Marlow as Marvin Mitchelson Courtney Friel as TV Reporter Peter Spruyt as Regional Buyer Derek Thompson as K.C. Jones Ashton Essex Bright as Young Fan John Romano as Marty