Will Smith Howard Inlet Edward Norton Whit Yardsham Kate Winslet Claire Wilson Michael Peña Simon Scott Helen Mirren Brigitte Jacob Latimore Raffi Keira Knightley Amy Moore Naomie Harris Madeleine Ann Dowd Sally Price Kylie Rogers Allison Yardsham Natalie Gold Beverly Liza Colón-Zayas Robin Shirley Rumierk Simon's Wife Alyssa Cheatham Olivia Mary Beth Peil Whit's Mother Andy Taylor Father with Photo Michael Cumpsty Chairman of the Board Joseph Castillo-Midyett Teacher (Mexican Commercial) Bryan Terrell Clark Homeless A Capella Singer Jimmy Palumbo Super Elia Monte-Brown Support Group Member Andres Munar Support Group Member Harriett D. Foy Board Member Maureen Mueller Board Member Steven Hauck Board Member Willie C. Carpenter Board Member Emily Bennett Restaurant Patron (uncredited) Madeline Lupi Marymount Student (uncredited) Reginald L. Barnes NYC Tourist (uncredited) Lily Peterson Marymount Student (uncredited)