The story of the five-day interview between Rolling Stone reporter David Lipsky and acclaimed novelist David Foster Wallace, which took place right after the 1996 publication of Wallace's groundbreaking epic novel, 'Infinite Jest.'
| Actor | Role |
|---|---|
 Jason SegelDavid Foster Wallace | David Foster Wallace |
 Jesse EisenbergDavid Lipsky | David Lipsky |
 Mamie GummerJulie | Julie |
 Mickey SumnerBetsy | Betsy |
 Johnny OttoPilot | Pilot |
 Anna ChlumskySarah | Sarah |
 Joan CusackPatty | Patty |
 Becky Ann BakerBookstore Manager | Bookstore Manager |
 Ron LivingstonDavid Lipsky's Editor | David Lipsky's Editor |
 Stephanie CottonUnited Ticket Agent | United Ticket Agent |
 Dan John MillerNPR Host | NPR Host |
| NNoel FletcherISU Student | ISU Student |
| MMichael J. StalmerNight Watchmen | Night Watchmen |
 Punnavith KoyMovie Goer | Movie Goer |
| BBen PhelpsMall Shopper | Mall Shopper |
 Joel ThingvallMovie Theater Usher (uncredited) | Movie Theater Usher (uncredited) |
| RRyan J. GilmerSkyway Passerby (uncredited) | Skyway Passerby (uncredited) |
 Alan HolasekBox Office Clerk (uncredited) | Box Office Clerk (uncredited) |