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

Lily Lodge

House Matron

Jordan Bridges

Spencer Jones

Ebon Moss-Bachrach

Charlie Stewart

Christopher Braden

Bartender

Chuck Montgomery

Tall Man

Taylor Roberts

Louise

John Scurti

Stan Sher

Ed Peed

Taxi Driver

Rony Clanton

Porter

Becky Veduccio

Blue Ship Hostess

Paul Vincent Black

Joseph O'Neil

Lisa Roberts Gillan

Miss Albini

June Miller

Cape Cod Hostess

Aleksa Palladino

Frances the Girl in Italian Class

Charles Techman

Harvard Dorm Monitor

Lauren Adler

Art History Student

Daisy Baldwin

Art History Student

Janine Barris

Art History Student

Emily Bauer

Art History Student

Kirstie Bingham

Art History Student

Jennifer Bowen

Art History Student

Angelique Claire

Art History Student

Nikki Coble

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

Rob Buntzen

Wedding Planner Host

Richard O'Rourke

Igor

Tori Amos

Singer

Brad Mehldau

Pianist

Chris Burke

Custodian

Canedy Knowles

Christmas Student

Liliane Thomas

Woman on Train

Kevin Anton

Harvard Student (uncredited)

Whitney Avalon

Almost-Hit Bike Rider (uncredited)

Anthony Backman

Sully Mason Impressionist (uncredited)

Eric Bruno Borgman

College Janitor (uncredited)

Marylouise Burke

Carr's Secretary (uncredited)

Jean Burns

Hoop Roller (uncredited)

Grenville Cuyler

Phillip McIntyre (uncredited)

John Farrer

Wedding Guest (uncredited)

Jeannette Gould

Faculty (uncredited)

Vivian Kalinov

Artist - Metal Sculptor (uncredited)

Trish McGettrick

Governor's Wife (uncredited)

Josh Mowery

Dancer (uncredited)

Randi Newton

Miranda (uncredited)

Amber Paul

Art History Student (uncredited)

James Donnell Quinn

Student (uncredited)

Maria Rusolo

Swing Dancer (uncredited)

Gabrielle Salinger

Hoop Girl (uncredited)

Melissa Goodwin Shepherd

Dancer (uncredited)

Frank Stellato

NYC Cabbie (uncredited)