Nicholas D'Agosto as Ben Wekselbaum

Margo Martindale as Coach Lumbly

Reece Thompson as Hal Hefner

Anna Kendrick as Ginny Ryerson

Jonah Hill as Junior Philosopher

Denis O'Hare as Doyle Hefner

Vincent Piazza as Earl Hefner

Aaron Yoo as Heston

Utkarsh Ambudkar as Ram

Candace Hammer as Townsend Prep Debater

Lisbeth Bartlett as Juliet Hefner

Virginia House as English Teacher

Marilyn Yoblick as Plainsboro Lunch Lady

Maury Ginsberg as Mr. Lewinsky

Emily Ginnona as Honoria

Dionne Audain as Abraham Lincoln

Dan De Luca as Stephen Douglas

Michael Kusnir as Flemming

Steve Park as Judge Pete

John Patrick Barry as Gym Teacher

Josh Kay as Lewis Garrles

Jane Beard as Fern Garries

Herb Merrick as Lewis's Dad

Carol Florence as connie Ryerson

Betsy Hogg as Crystal Hamish-Steinberg

Brandon Thane Wilson as Philip

David DeBoy as Frank Ryerson

Andrew Collie as Hazlet Timer

Susan Duvall as Hazlet Lunch Lady

Elisabeth Noone as Hazlet Coach

Jeanette Brox as Townsend Prep Bad Girl

Roland Gomez as Luis

Lee Sellars as New Jersey Debate Official

Joel Marsh Garland as Pizza Server

Dan Cashman as Narrator (voice)