Director:Steven Shainberg
Writer:Erin Cressida Wilson, Mary Gaitskill
Producer:Jamie Beardsley, Andrew Fierberg, Amy Hobby, Joel Posner
Studio:SUNFILM Entertainment
Genre:Comedy, Drama, Romance
Lee Holloway is a smart, quirky woman in her twenties who returns to her hometown in Florida after a brief stay in a mental hospital. In search of relief from herself and her oppressive childhood environment, she starts to date a nerdy friend from high school and takes a job as a secretary in a local law firm, soon developing an obsessive crush on her older boss, Mr. Grey. Through their increasingly bizarre relationship, Lee follows her deepest longings to the heights of masochism and finally to a place of self-affirmation.
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
Oz 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 (as Russell Harper)
David Wiater Tomato Date
Shannon Convery New Secretary
Alison Tatlock TV Reporter
Emmy Collins Zoo Protester (uncredited)
Diane McGee Woman with the Purple Boots (uncredited)
Cali T. Rossen Dancing Party Guest (uncredited)
Steven Shainberg Richard Arevalos (sex therapist on tape) (voice) (uncredited)
Erin Cressida Wilson Sitting In Mr. Grey's Waiting Room (uncredited)
Angelo Badalamenti Composer
Pam Wise Editor
DVD Details
Sound:Dolby SR
Aspect Ratio:1.85 : 1
Release:Apr 2004