| Older Actor; Younger Actor | Movie | Character (Year) |
| Richard Dreyfuss; Wil Wheaton | |
| Harrison Ford; River Phoenix | |
| Burt Lancaster; Frank Whaley | |
| Samantha Mathis; Kirsten Dunst | |
| Rosie O'Donnell; Christina Ricci | |
| Bonnie Hunt; Laura Bell Bundy | |
| Brad Pitt; Brad Renfro | |
| Gloria Stuart; Kate Winslet | |
| Parker Posey; Rachael Leigh Cook | |
| Jodie Foster; Jena Malone | |
| Angelina Jolie; Mila Kunis | |
| Robert Wagner; Rob Lowe | |
| John Cusack; Drake Bell | |