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)