| Ken Burns | Himself |
| Bill Clinton | Himself |
| Neal Conan | Himself |
| Stella Daily | Herself |
| Jon Delfin | Himself |
| Bob Dole | Himself |
| Brian Dominy | Himself |
| Vic Fleming | Himself |
| Tyler Hinman | Himself |
| Mike Mussina | Himself |
| Chris Astoyan | Himself |
| Judie Berger | Herself |
| Leslie Billig | Herself |
| Dr. Selmer Bringsjord | Himself |
| Katherine Bryant | Herself |
| Eleanor Dantignac | Herself |
| Jon Stewart | |
| Miriam Raphael | |
| Dan Katz (III) | |
| Daniel Okrent | |
| Alex Ripitsky | |
| Amy Ray | |
| Merl Reagle | |
| Indigo Girls | |
| Will Shortz |
| Director | Patrick Creadon |
| Producer | Michael Creadon; Christine O'Malley |
| Writer | Patrick Creadon; Christine O'Malley |
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| Feature Commentary with Director Patrick Creadon, The New York Times Crossword Editor Will Shortz and Crossword Constructor Merl Reagle Deleted Scenes Interview Gallery 5 Unforgettable Puzzles, Featurettes Wordplay Goes to Sundance "Every Word", a Music Video by Gary Louris Waiting For The New York Times ·A Short Film by Patricia Erens Wordplay Photo Gallery DVD-Rom Enabled - 5 Unforgettable Puzzles! |