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Should I Watch..? 'Secretary' (2002)

Benjamin is a former volunteer DJ at his local hospital radio station. He has been reviewing films online since 2004.

Film's poster

Film's poster

What's the big deal?

Secretary is a romantic comedy-drama film released in 2002 and is loosely based on the short story Bad Behaviour by Mary Gaitskill. The film stars Maggie Gyllenhaal and James Spader as co-workers who develop an intense and unconventional relationship with each other. The film also stars Jeremy Davis and Lesley Ann Warren and was directed by Steven Shainberg. The film proved to be Gyllenhaal's break-out appearance with critics lauding her performance as well as that of Spader. Made for just $4 million and released in only a limited number of theatres, the film went on to make more than $9.3 million worldwide and undoubtedly served as an inspiration for the makers of another BDSM-based romance, Fifty Shades Of Grey.


What's it about?

Lee Holloway is an insecure and troubled young woman, released back into the care of her dysfunctional family after spending time in an institute to cure a self-harming habit. Struggling to keep her impulses in check, the socially awkward Lee decides to get a job and somehow secures a secretarial position for kooky lawyer E. Edward Grey. However, there is evidence that not all is as it seems - despite his insistence that the work is very dull, Lee happily embraces the position.

Soon, however, Lee's typos and odd behaviour attract Grey's attention and with ever-increasing boldness, his propensity for BDSM shows itself. Initially confused, Lee begins discovering her own feelings for Grey and finds herself slowly falling for him. Can these two oddballs find some common ground and what does this all mean for Lee's childhood sweetheart Peter?


What's to like?

Indie films like this tend to rely on two things, generally speaking - the script and the cast. On the latter, the film has two fabulous performances from Gyllenhaal and Spader, possibly the best of his career. Spader can play sexual deviants in his sleep (no disrespect intended!) as anyone who watched Crash will testify but Gyllenhaal is a revelation, delivering a perfectly pitched performance of a woman unsure of herself and discovering new facets of her personality. The evolution of her character, from scared and naïve to determined and strong, is worth the ticket price alone. Alongside them, Warren does well as the heavily-medicated mother and Davis generates sympathy as Lee's boyfriend who has no idea what he's getting caught up in.

The film's script is also first-class. It manages to avoid becoming sordid or exploitative but also keeps the more unusual aspects of the subject matter on show, never shying away from some truly alien behaviour to those of us outside the BDSM community. The sight of Lee manacled to a metal bar or wearing a saddle with a carrot in her mouth is both illuminating and disturbing although the film also works hard to inject humour into proceedings. I especially enjoyed the scene where Lee begins spanking herself with a hairbrush and wondering why it doesn't feel the same as when her boss does it.

The film is unusual and certainly 'out there' in places but it's never exploitative and is surprisingly sensitive about its taboo subject matter.

The film is unusual and certainly 'out there' in places but it's never exploitative and is surprisingly sensitive about its taboo subject matter.

Fun Facts

  • One of the film posters depicts a secretary from the rear, leaning forward at a provocative angle. Gyllenhaal admitted that she is not the model in the poster but that she was someone dating her ex-boyfriend at the time.
  • Insisting that she was not exploited during the shoot, Gyllenhaal has been somewhat guarded when discussing the film. She admits that she was scared at the beginning of the shoot and that director Shainberg "was daring me to take a risk and I did."
  • Screenwriter Erin Cressida Wilson has a brief cameo in Mr Grey's waiting room, one of three people waiting to see him.
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What's not to like?

The strange thing about Secretary is that it's never entirely sure when you should laugh at it. Yes, some of the more bizarre antics shown do warrant a giggle because they are simply so unusual. But it does feel very creepy at times, no thanks to Spader's faultless performance as the domineering boss falling in love against his better judgement. The film does have scenes that are uncomfortable to watch but at least they feel much more genuine than anything E.L. James cooked up in her Twilight fan fiction. The chemistry between Spader and Gyllenhaal makes the film feel more like an unconventional romance than a badly written, cheap skin flick.

The film isn't a riotous comedy but it's a refreshing change to see something of a taboo subject matter treated with respect. It attempts to make BDSM feel normal and while it doesn't quite work, it at least shows that it works for these characters. However strange and unfathomable their relationship may seem to us, it works for them and instead of demonising such behaviour, the film shines a positive light on it. In a weird way, this feels more realistic than any number of Hollywood films dealing with sex - it lacks the lurid glamour of something like Basic Instinct or Showgirls but is all the better because of it.

Gyllenhaal's performance is heart-breaking, humorous and brave, given the unconventional subject matter.

Gyllenhaal's performance is heart-breaking, humorous and brave, given the unconventional subject matter.

Should I watch it?

It won't be for everybody but thank God that Secretary is daring and brave enough to be something different for audiences wanting to order off the menu. It offers an eye-opening look at a subject matter many people still consider immoral but portrays it as just another angle for two people to find each other. The film isn't as shocking as perhaps you think it is but for those of you open-minded enough, this is a heart-warming and life-affirming look at two of cinema's strangest star-crossed lovers.

Great For: BDSM enthusiasts, starting conversations, Gyllenhaal's career, office-based romances

Not So Great For: your grandparents, babysitters, possibly actual secretaries

What else should I watch?

BDSM isn't a subject covered that often in mainstream cinema, usually popping up in a single sex scene in otherwise forgettable erotic thrillers like Fifty Shades Of Grey or Body Of Evidence or desperate comedies. Even fewer films look at the subject as objectively and intelligently as Secretary - French drama La Pianiste (The Piano Teacher) studies the relationship dynamics between a music teacher and her pupil but I found it to be a slow, plodding affair. Other than that, most producers seem to avoid the topic like a clap-ridden whore.

To say that the movie launched Gyllenhaal onto the A-list is somewhat misleading. She first made her name opposite her brother Jake in the trippy indie drama Donnie Darko but would go on to appear in critical acclaimed films like The Dark Knight replacing Katie Holmes as Assistant DA Rachel Dawes, the lead role in another indie drama Sherrybaby and would be Oscar-nominated for her performance opposite Jeff Bridges in Crazy Heart. With a rock-solid reputation for dependable performances that occasionally push the envelope, her career can only continue its upward trend.

Main Cast


Maggie Gyllenhaal

Lee Holloway

James Spader

E. Edward Grey

Jeremy Davis


Lesley Ann Warren

Joan Holloway

Stephen McHattie

Burt Holloway

Technical Info

*based on the short story 'Bad Behaviour' by Mary Gaitskill, adapted by Erin Cressida Wilson & Steven Shainberg

DirectorSteven Shainberg


Erin Cressida Wilson *

Running Time

107 minutes

Release Date (UK)

16th May, 2003




Comedy, Drama, Romance

© 2018 Benjamin Cox

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