Julia Roberts as Katherine Ann Watson

Kirsten Dunst as Betty Warren

Julia Stiles as Joan Brandwyn

Maggie Gyllenhaal as Giselle Levy

Ginnifer Goodwin as Connie Baker

Dominic West as Bill Dunbar

Juliet Stevenson as Amanda Armstrong

Marcia Gay Harden as Nancy Abbey

John Slattery as Paul Moore

Marian Seldes as President Jocelyn Carr

Donna Mitchell as Mrs. Warren

Terence Rigby as Dr. Edward Staunton

Jennie Eisenhower as Girl at the Station

Leslie Lyles as Housing Director

Laura Allen as Susan Delacorte

Topher Grace as Tommy Donegal

Lily Lodge as House Matron

Jordan Bridges as Spencer Jones

Ebon Moss-Bachrach as Charlie Stewart

Chuck Montgomery as Tall Man

Taylor Roberts as Louise

John Scurti as Stan Sher

Ed Peed as Taxi Driver

Rony Clanton as Porter

Becky Veduccio as Blue Ship Hostess

Paul Vincent Black as Joseph O'Neil

Lisa Roberts Gillan as Miss Albini

June Miller as Cape Cod Hostess

Aleksa Palladino as Frances the Girl in Italian Class

Charles Techman as Harvard Dorm Monitor

Lauren Adler as Art History Student

Daisy Baldwin as Art History Student

Janine Barris as Art History Student

Emily Bauer as Art History Student

Kirstie Bingham as Art History Student

Jennifer Bowen as Art History Student

Angelique Claire as Art History Student

Nikki Coble as Art History Student

Kristen Connolly as Art History Student

Kristyn Coppola as Art History Student

Kimberly Ehly as Art History Student

Megan Marie Ford as Art History Student

Lauren Fruchter as Art History Student

Kate Glass as Art History Student

Amanda Gruss as Art History Student

Stella Hao as Art History Student

Walker Hays as Art History Student

Michele Hillen as Art History Student

Annika Marks as Art History Student

Amy Montminy as Art History Student

Lily Rabe as Art History Student

Kate Reilly as Art History Student

Krysten Ritter as Art History Student

Brandy Tipton as Art History Student

Trisha Trokan as Art History Student

Megan Tropea as Art History Student

Maja Wampuszyc as Art History Student

Mary Pascoe as Photographer

Elise Passamani as Phyllis

Laura M. Flahive as Wet Girl

Devon Jencks as Wet Girl

Erin E. Richardson as Wet Girl

Emily R. See as Wet Girl

Rob Buntzen as Wedding Planner Host

Richard O'Rourke as Igor

Chris Bonomo as Groomsman

Katherine Argo as Dancer

Shelby Bond as Dancer

Lou Brock as Dancer

Michael Choi as Dancer

Melissa Deles as Dancer

John D. Fowler as Dancer

Nicole Frydman as Dancer

Noelle Gibson as Dancer

Maria Vicens Girau as Dancer

Natalie Gomez as Dancer

Sid Grant as Dancer

Madeleine Hackney as Dancer

Betina Hershey as Dancer

Yuval Hod as Dancer

Richard Jones as Dancer

Jerry Jordan as Dancer

Nickolay Khazanov as Dancer

Nadia Kravets as Dancer

Maria Levinstein as Dancer

KellyDawn Malloy as Dancer

Annette Nicole as Dancer

Lance Olds as Dancer

Joe Palmer as Dancer

Christian Perry as Dancer

Daniel Ponickly as Dancer

Tony Scheppler as Dancer

Solomon Singer as Dancer

Gabriel Vaughan as Dancer

Kim Villanueva as Dancer

Dan Weltner as Dancer

Sarah Billings Wheeler as Dancer

Denise Zadroga as Dancer

Peter J. Rowan as Wedding Photographer

Tori Amos as Singer

Kevin Osborne as Band Announcer

Brad Mehldau as Pianist

Larry Grenadier as Bass Player

Julie Wagner as Bartender

Jennifer Anderson as Projectionist

Lindsey White as Projectionist

Chris Burke as Custodian

Dorothy Dwyer as Faculty

Melanie Angelique Moyer as Christmas Student

Canedy Knowles as Christmas Student

Kristen Marie Holly as Christmas Student

Carrie Ann Kaye as Christmas Student

Liliane Thomas as Woman on Train

Jackie Sanders as Band Announcer

Anna Fields as Eleanor Warren (uncredited)

Valerie Vaile as Jane Whitmore (uncredited)

Jill Whitaker as Vanessa McIntyre (uncredited)

Randi Newton as Miranda (uncredited)

Grenville Cuyler as Phillip McIntyre (uncredited)

Erik Davies as Robert Flint (uncredited)

Gunna Wilson as Spencer's Girlfriend (uncredited)

Corey W. Allen as Giselle's Wedding Date (uncredited)

Marylouise Burke as President Jocelyn Carr's Secretary (uncredited)

Trish McGettrick as Governor's Wife (uncredited)

Jeannette Gould as Faculty (uncredited)

Whitney Avalon as Almost-Hit Bike Rider (uncredited)

Eric Bruno Borgman as College Janitor (uncredited)

Cristie Schoen Codd as Alto Sax Player (uncredited)

Katrina Connor as Art History Student (uncredited)

Marlo DiCrasto as Art History Student (uncredited)

Ashley Dru Douglass as Art History Student (uncredited)

Liesl Ehardt as Joan Brandwyn's Friend (uncredited)

Jessica Leigh Johnson as Art History Student (uncredited)

Marni Penning as Art History Student (uncredited)

Dina Rose Rivera as Art History Student (uncredited)

Melissa Goodwin Shepherd as Dancer (uncredited)

Josh Mowery as Dancer (uncredited)

Matthew Shaffer as Dancer (uncredited)

Michael Cuomo as Swing Dancer (uncredited)

Maria Rusolo as Swing Dancer (uncredited)

Christopher Braden as Bartender