Patricia Rozema Director Abigail Breslin Kit Kittredge Actor Joan Cusack Miss Bond Actor Jane Krakowski Miss Dooley Actor Stanley Tucci Mr. Berk Actor Chris O'Donnell Mr. Kittredge Actor Julia Ormond Mrs. Kittredge Actor Glenne Headly Mrs. Howard Actor Max Thieriot Will Shepherd Actor Madison Davenport Ruthie Smithens Actor Zach Mills Stirling Howard Actor Colin Mochrie Mr. Pennington Actor Wallace Shawn Mr. Gibson Actor Willow Smith Countee Actor Ann Peacock Screenwriter Elaine Goldsmith-Thomas Producer Ellen L. Brothers Producer Lisa Roberts Gillan Producer Julie Goldstein Producer Julia Roberts Executive Producer Marisa Yeres Executive Producer David Boyd Cinematographer Julie Rogers Film Editing Joseph Vitarelli Original Music Peter Cosco Production Design Michele Brady Art Director Odetta Stoddard Set Decoration Trysha Bakker Costume Design Nancy Nayor Casting