Will Smith Richard Williams Aunjanue Ellis-Taylor Oracene "Brandy" Price Saniyya Sidney Venus Williams Demi Singleton Serena Williams Jon Bernthal Rick Macci Tony Goldwyn Paul Cohen Susie Abromeit Robin Finn Dylan McDermott Will Hodges Judith Chapman Nancy Reagan Erin Cummings Social Worker Katrina Begin Anne Worchester Andy Bean Laird Stabler Kevin Dunn Vic Braden Craig Tate Bells Layla Crawford Lyndrea Price Noah Bean PV CC Tennis Pro Josiah Cross TD Vaughn W. Hebron Monsta Jimmy Walker Jr. Old Patron Brad Greenquist Bud Collins Johnno Wilson Incredulous Pro Christopher Wallinger John McEnroe Andy Hoff Stacey's Dad - Trevor Carrie Gibson Line Judge Doug Simpson Girl #3 Father Brandon Morales Deputy #1 Wil J. Jackson Deputy #2 Rich Sommer Patrick Dougherty Danya LaBelle Tournament Official - Oakland Coliseum Mel Fair Male TV Announcer