Cameron Diaz Elizabeth Halsey Justin Timberlake Scott Delacorte Jason Segel Russell Gettis Lucy Punch Amy Squirrel John Michael Higgins Principal Wally Snur Phyllis Smith Lynn Davies Thomas Lennon Carl Halabi Molly Shannon Melody (Garrett's Mom) Eric Stonestreet Kirk Dave Allen Sandy Pinkus Kaitlyn Dever Sasha Abernathy Jillian Armenante Ms. Pavicic Kathryn Newton Chase Rubin-Rosse Andra Nechita Gaby Noah Munck Tristan Finneas O'Connell Spencer Paul Bates School Superintendent Nat Faxon Mark Cameron Diaz Elizabeth Halsey Justin Timberlake Scott Delacorte Jason Segel Russell Gettis Lucy Punch Amy Squirrel John Michael Higgins Principal Wally Snur Phyllis Smith Lynn Davies Thomas Lennon Carl Halabi Molly Shannon Melody (Garrett's Mom) Eric Stonestreet Kirk Dave Allen Sandy Pinkus Kaitlyn Dever Sasha Abernathy Jillian Armenante Ms. Pavicic Kathryn Newton Chase Rubin-Rosse Andra Nechita Gaby Noah Munck Tristan Finneas O'Connell Spencer Paul Bates School Superintendent Nat Faxon Mark Stephanie Faracy Mrs. Pubich David Paymer Doctor Vogel Alanna Ubach Angela Paul Feig Dad at Carwash Deirdre Lovejoy Sasha's Mother Rose Abdoo School Secretary Jerry Lambert Morgan's Dad Jennifer Irwin Chase's Mom Rick Overton Philip Matt Besser Abraham Lincoln (Tour Guide) Lee Eisenberg Blacksmith (Re-Enactor) Bruno Gunn Police Officer Jennifer Holloway Sheila (uncredited) Cameron Diaz Elizabeth Halsey Justin Timberlake Scott Delacorte Jason Segel Russell Gettis Lucy Punch Amy Squirrel John Michael Higgins Principal Wally Snur Phyllis Smith Lynn Davies Thomas Lennon Carl Halabi Molly Shannon Melody (Garrett's Mom) Eric Stonestreet Kirk Dave Allen Sandy Pinkus Kaitlyn Dever Sasha Abernathy Jillian Armenante Ms. Pavicic Kathryn Newton Chase Rubin-Rosse Andra Nechita Gaby Noah Munck Tristan Finneas O'Connell Spencer Paul Bates School Superintendent Nat Faxon Mark Stephanie Faracy Mrs. Pubich David Paymer Doctor Vogel Alanna Ubach Angela Paul Feig Dad at Carwash Deirdre Lovejoy Sasha's Mother Rose Abdoo School Secretary Jerry Lambert Morgan's Dad Jennifer Irwin Chase's Mom Rick Overton Philip Matt Besser Abraham Lincoln (Tour Guide) Lee Eisenberg Blacksmith (Re-Enactor) Bruno Gunn Police Officer Jennifer Holloway Sheila (uncredited)