Julia Roberts

Katherine Ann Watson

Kirsten Dunst

Betty Warren

Julia Stiles

Joan Brandwyn

Maggie Gyllenhaal

Giselle Levy

Ginnifer Goodwin

Connie Baker

Dominic West

Bill Dunbar

Juliet Stevenson

Amanda Armstrong

Marcia Gay Harden

Nancy Abbey

John Slattery

Paul Moore

Marian Seldes

President Jocelyn Carr

Donna Mitchell

Mrs. Warren

Terence Rigby

Dr. Edward Staunton

Jennie Eisenhower

Girl at the Station

Leslie Lyles

Housing Director

Laura Allen

Susan Delacorte

Topher Grace

Tommy Donegal

Jordan Bridges

Spencer Jones

Ebon Moss-Bachrach

Charlie Stewart

Chuck Montgomery

Tall Man

Taylor Roberts

Louise

John Scurti

Stan Sher

Rony Clanton

Porter

Lisa Roberts Gillan

Miss Albini

Aleksa Palladino

Frances the Girl in Italian Class

Charles Techman

Harvard Dorm Monitor

Lauren Adler

Art History Student

Janine Barris

Art History Student

Emily Bauer

Art History Student

Kristen Connolly

Art History Student

Annika Marks

Art History Student

Lily Rabe

Art History Student

Kate Reilly

Art History Student

Krysten Ritter

Art History Student

Maja Wampuszyc

Art History Student

Mary Pascoe

Photographer

Katherine Argo

Dancer

Kim Villanueva

Dancer

Tori Amos

Singer

Kevin Osborne

Band Announcer

Brad Mehldau

Pianist

Julie Wagner

Bartender

Chris Burke

Custodian

Dorothy Dwyer

Faculty

Canedy Knowles

Christmas Student

Kristen Marie Holly

Christmas Student

Marylouise Burke

President Jocelyn Carr's Secretary (uncredited)

Whitney Avalon

Almost-Hit Bike Rider (uncredited)

Eric Bruno Borgman

College Janitor (uncredited)

Liesl Ehardt

Joan Brandwyn's Friend (uncredited)

Marni Penning

Art History Student (uncredited)

Melissa Goodwin Shepherd

Dancer (uncredited)

Josh Mowery

Dancer (uncredited)

Michael Cuomo

Swing Dancer (uncredited)

Maria Rusolo

Swing Dancer (uncredited)

Christopher Braden

Bartender