James Spader
Mr. Grey
Maggie Gyllenhaal
Lee Holloway
Jeremy Davies
Peter
Lesley Ann Warren
Joan Holloway
Stephen McHattie
Burt Holloway
Patrick Bauchau
Dr. Twardon
Jessica Tuck
Tricia O'Connor
Osgood Perkins
Jonathan
Amy Locane
Lee's Sister
Mary Joy
Sylvia
Michael Mantell
Stewart
Lily Knight
Paralegal
Sabrina Grdevich
Allison
Lacey Kohl
Louisa
Julene Renee
Jessica
Lauren Cohn
First Secretary
Ezra Buzzington
Typing Teacher
Kyle Colerider-Krugh
Mr. Garvey
Steven Fierberg
First Date
Herbert Russell
Second Date
David Wiater
Tomato Date
Shannon Convery
New Secretary
Alison Tatlock
TV Reporter
Christina Gray
Photographer (uncredited)
Cali T. Rossen
Dancing Party Guest (uncredited)
Diane McGee
Woman in the Purple Boots (uncredited)
Steven Shainberg
Richard Arevalos (Sex Therapist on Tape) (voice) (uncredited)
Erin Cressida Wilson
Sitting In Mr. Grey's Waiting Room (uncredited)
Amy Hobby
Producer
Erin Cressida Wilson
Screenplay
Pam Wise
Editor
Angelo Badalamenti
Original Music Composer
Steven Shainberg
Director
Steven Shainberg
Producer
Andrew Fierberg
Producer
Steven Fierberg
Director of Photography
Sharon Cingle
Script Supervisor
José Ignacio Álvarez
Stunt Coordinator
Rebekah Schultz
Assistant Property Master
Jamie Beardsley
Executive Producer
Raqueli Dahan
Makeup Department Head
Joel Posner
Executive Producer
Robin Jacobson
Property Master
Michael Roban
Executive Producer
P.J. Posner
Executive Producer
Kyle A. Clark
Production Manager
Allison Siegel
Costume Supervisor
Nick Ralbovsky
Art Direction
Amy Danger
Production Design
John Foster
Second Unit Director of Photography
Jim Simone
Second Assistant Director
Kiran Gonsalves
First Assistant Director
Carl Lawrence Ludwig
First Assistant Director
Marguerite Happy
Stunt Double
Vince P. Maggio
First Assistant Director
Marjorie Bowers
Costume Design
Ellen Parks
Casting
Jay Rabinowitz
Additional Editing
Erin Cressida Wilson
Story Developer
Steven Shainberg
Story Developer
Benjamin Wolf
First Assistant Camera
Mary Gaitskill
Short Story
Kenji Luster
Steadicam Operator