| When Did... | Movie |
| Will Farrell Play a Playwright? | |
| Tom Hanks Play a Band Manager? | |
| Michael Keaton Play a Snowman? | |
| Leonardo DiCaprio Play the King of France? | |
| Tom Cruise Play a Vampire? | |
| Sylvester Stallone Play A Super Villain? | |
| James Earl Jones Play a White Guy? | |
| Christian Bale Play a Magician? | |
| Mike Myers Play a World War II General? | |
| Johnny Depp Play a Bank Robber? | |