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