James Spader

Character: Mr. Grey

Maggie Gyllenhaal

Character: Lee Holloway

Jeremy Davies

Character: Peter

Lesley Ann Warren

Character: Joan Holloway

Stephen McHattie

Character: Burt Holloway

Patrick Bauchau

Character: Dr. Twardon

Jessica Tuck

Character: Tricia O'Connor

Osgood Perkins

Character: Jonathan

Amy Locane

Character: Lee's Sister

Mary Joy

Character: Sylvia

Michael Mantell

Character: Stewart

Lily Knight

Character: Paralegal

Sabrina Grdevich

Character: Allison

Lacey Kohl

Character: Louisa

Julene Renee

Character: Jessica

Lauren Cohn

Character: First Secretary

Ezra Buzzington

Character: Typing Teacher

Kyle Colerider-Krugh

Character: Mr. Garvey

Steven Fierberg

Character: First Date

Herbert Russell

Character: Second Date

David Wiater

Character: Tomato Date

Shannon Convery

Character: New Secretary

Alison Tatlock

Character: TV Reporter

Christina Gray

Character: Photographer (uncredited)

Cali T. Rossen

Character: Dancing Party Guest (uncredited)

Diane McGee

Character: Woman in the Purple Boots (uncredited)

Steven Shainberg

Character: Richard Arevalos (Sex Therapist on Tape) (voice) (uncredited)

Erin Cressida Wilson

Character: Sitting In Mr. Grey's Waiting Room (uncredited)