| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| This 2-time Oscar winner appeared as an extra on "Little House on the Prairie" before making his film debut in "Taps" | Sean Penn | $2,000 | DJ | ACTORS & THEIR ROLES | 2025-06-11 | #9353 | |
| He adapted "Into the Wild" | Sean Penn | $800 | J | ACTORS WHO WRITE | 2014-01-03 | #6745 | |
| "The Pledge" &"Into the Wild" | Sean Penn | $600 | J | ACTORS WHO DIRECT | 2011-02-16 | #6088 |