David Foster Wallace

Jason Segel

David Lipsky

Jesse Eisenberg

Bookstore Manager

Becky Ann Baker

Sarah

Anna Chlumsky

Julie

Mamie Gummer

Patty

Joan Cusack

Betsy

Mickey Sumner

Pilot

Johnny Otto

David Lipsky's Editor

Ron Livingston

Movie Goer

Punnavith Koy

United Ticket Agent

Stephanie Cotton

NPR Host

Dan John Miller

ISU Student

Noel Fletcher

Night Watchmen

Michael J. Stalmer

Mall Shopper

Ben Phelps

Movie Theater Usher (uncredited)

Joel Thingvall

Skyway Passerby (uncredited)

Ryan J. Gilmer

Box Office Clerk (uncredited)

Alan Holasek