Julia Roberts
Role: Katherine Ann Watson
Kirsten Dunst
Role: Betty Warren
Julia Stiles
Role: Joan Brandwyn
Maggie Gyllenhaal
Role: Giselle Levy
Ginnifer Goodwin
Role: Connie Baker
Dominic West
Role: Bill Dunbar
Juliet Stevenson
Role: Amanda Armstrong
Marcia Gay Harden
Role: Nancy Abbey
John Slattery
Role: Paul Moore
Marian Seldes
Role: President Jocelyn Carr
Donna Mitchell
Role: Mrs. Warren
Terence Rigby
Role: Dr. Edward Staunton
Jennie Eisenhower
Role: Girl at the Station
Leslie Lyles
Role: Housing Director
Laura Allen
Role: Susan Delacorte
Topher Grace
Role: Tommy Donegal
Lily Lodge
Role: House Matron
Jordan Bridges
Role: Spencer Jones
Ebon Moss-Bachrach
Role: Charlie Stewart
Chuck Montgomery
Role: Tall Man
Taylor Roberts
Role: Louise
John Scurti
Role: Stan Sher
Becky Veduccio
Role: Blue Ship Hostess
Paul Vincent Black
Role: Joseph O'Neil
Lisa Roberts Gillan
Role: Miss Albini
June Miller
Role: Cape Cod Hostess
Aleksa Palladino
Role: Frances the Girl in Italian Class
Charles Techman
Role: Harvard Dorm Monitor
Lauren Adler
Role: Art History Student
Daisy Baldwin
Role: Art History Student
Janine Barris
Role: Art History Student
Emily Bauer
Role: Art History Student
Kirstie Bingham
Role: Art History Student
Jennifer Bowen
Role: Art History Student
Angelique Claire
Role: Art History Student
Nikki Coble
Role: Art History Student
Kristen Connolly
Role: Art History Student
Kristyn Coppola
Role: Art History Student
Kimberly Ehly
Role: Art History Student
Megan Marie Ford
Role: Art History Student
Lauren Fruchter
Role: Art History Student
Kate Glass
Role: Art History Student
Amanda Gruss
Role: Art History Student
Stella Hao
Role: Art History Student
Walker Hays
Role: Art History Student
Michele Hillen
Role: Art History Student
Annika Marks
Role: Art History Student
Amy Montminy
Role: Art History Student
Lily Rabe
Role: Art History Student
Kate Reilly
Role: Art History Student
Krysten Ritter
Role: Art History Student
Brandy Tipton
Role: Art History Student
Trisha Trokan
Role: Art History Student
Megan Tropea
Role: Art History Student
Maja Wampuszyc
Role: Art History Student
Mary Pascoe
Role: Photographer
Elise Passamani
Role: Phyllis
Laura M. Flahive
Role: Wet Girl
Devon Jencks
Role: Wet Girl
Erin E. Richardson
Role: Wet Girl
Emily R. See
Role: Wet Girl
Rob Buntzen
Role: Wedding Planner Host
Richard O'Rourke
Role: Igor
Chris Bonomo
Role: Groomsman
Katherine Argo
Role: Dancer
Melissa Deles
Role: Dancer
John D. Fowler
Role: Dancer
Nicole Frydman
Role: Dancer
Noelle Gibson
Role: Dancer
Maria Vicens Girau
Role: Dancer
Natalie Gomez
Role: Dancer
Madeleine Hackney
Role: Dancer
Betina Hershey
Role: Dancer
Richard Jones
Role: Dancer
Nickolay Khazanov
Role: Dancer
Nadia Kravets
Role: Dancer
Maria Levinstein
Role: Dancer
KellyDawn Malloy
Role: Dancer
Annette Nicole
Role: Dancer
Christian Perry
Role: Dancer
Daniel Ponickly
Role: Dancer
Tony Scheppler
Role: Dancer
Solomon Singer
Role: Dancer
Gabriel Vaughan
Role: Dancer
Kim Villanueva
Role: Dancer
Sarah Billings Wheeler
Role: Dancer
Denise Zadroga
Role: Dancer
Peter J. Rowan
Role: Wedding Photographer
Kevin Osborne
Role: Band Announcer
Brad Mehldau
Role: Pianist
Larry Grenadier
Role: Bass Player
Julie Wagner
Role: Bartender
Jennifer Anderson
Role: Projectionist
Lindsey White
Role: Projectionist
Chris Burke
Role: Custodian
Dorothy Dwyer
Role: Faculty
Melanie Angelique Moyer
Role: Christmas Student
Canedy Knowles
Role: Christmas Student
Kristen Marie Holly
Role: Christmas Student
Carrie Ann Kaye
Role: Christmas Student
Liliane Thomas
Role: Woman on Train
Jackie Sanders
Role: Band Announcer
Anna Fields
Role: Eleanor Warren (uncredited)
Valerie Vaile
Role: Jane Whitmore (uncredited)
Jill Whitaker
Role: Vanessa McIntyre (uncredited)
Randi Newton
Role: Miranda (uncredited)
Grenville Cuyler
Role: Phillip McIntyre (uncredited)
Erik Davies
Role: Robert Flint (uncredited)
Gunna Wilson
Role: Spencer's Girlfriend (uncredited)
Corey W. Allen
Role: Giselle's Wedding Date (uncredited)
Marylouise Burke
Role: President Jocelyn Carr's Secretary (uncredited)
Trish McGettrick
Role: Governor's Wife (uncredited)
Jeannette Gould
Role: Faculty (uncredited)
Whitney Avalon
Role: Almost-Hit Bike Rider (uncredited)
Eric Bruno Borgman
Role: College Janitor (uncredited)
Cristie Schoen Codd
Role: Alto Sax Player (uncredited)
Katrina Connor
Role: Art History Student (uncredited)
Marlo DiCrasto
Role: Art History Student (uncredited)
Ashley Dru Douglass
Role: Art History Student (uncredited)
Liesl Ehardt
Role: Joan Brandwyn's Friend (uncredited)
Jessica Leigh Johnson
Role: Art History Student (uncredited)
Marni Penning
Role: Art History Student (uncredited)
Dina Rose Rivera
Role: Art History Student (uncredited)
Melissa Goodwin Shepherd
Role: Dancer (uncredited)
Josh Mowery
Role: Dancer (uncredited)
Matthew Shaffer
Role: Dancer (uncredited)
Michael Cuomo
Role: Swing Dancer (uncredited)
Maria Rusolo
Role: Swing Dancer (uncredited)
Christopher Braden
Role: Bartender
