Honestly, if you mention Secretary today, most people immediately think of 50 Shades of Grey. They think it’s just some early-2000s indie version of a billionaire with a whip. But they’re wrong.
Actually, they're wildly wrong.
Maggie Gyllenhaal in Secretary isn't a precursor to Christian Grey’s "Red Room of Pain." It’s something much weirder, much more tender, and—if we're being real—way more radical. Gyllenhaal plays Lee Holloway, a woman who doesn't just "stumble" into a kinky relationship. She basically engineers it to save her own life.
It’s been over twenty years since this movie hit Sundance, and we're still talking about it. Why? Because Maggie Gyllenhaal did something with that role that almost no one else was doing at the time. She took a character who, on paper, looks like a victim—a self-harming, shy, "broken" girl—and turned her into the most empowered person in the room.
The Performance That Defined a Career
Maggie Gyllenhaal was only 22 when she took this role. Think about that. Most actors that age are still trying to figure out how to look cool on camera. She, instead, decided to play a woman who crawls across a floor to deliver a letter with a look of pure, ecstatic devotion.
It’s a fearless performance.
You’ve got to remember the context of 2002. Hollywood wasn't exactly overflowing with nuanced takes on BDSM or mental health. Usually, a character who cuts herself is treated with a sort of "After School Special" pity. But Gyllenhaal’s Lee Holloway isn't looking for a hug. She’s looking for a container for her chaos.
When she meets E. Edward Grey, played by the perpetually intense James Spader, something clicks. It’s not "love at first sight" in the Hallmark sense. It’s more like "mutual recognition of weirdness at first sight."
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The way Gyllenhaal uses her body in this film is a masterclass. She starts off slumped, eyes darting, looking like she’s trying to disappear into the wallpaper. By the end? She’s glowing. She’s upright. She’s found a way to be "seen" that doesn't involve a hospital bed.
Why It’s Not Just "Early 50 Shades"
The biggest misconception about Maggie Gyllenhaal in Secretary is that the power dynamic is one-sided. People see Spader’s Mr. Grey barking orders and think, Oh, he’s the boss. But look closer.
Who is really driving the bus here?
- Lee deliberately makes typos.
- She pushes his buttons to provoke a reaction.
- When he tries to push her away, she literally refuses to move.
There’s a scene where she sits in his office, unmoving, for days. She’s proving her devotion, sure, but she’s also forcing him to confront his own needs. She’s essentially holding him hostage with her submission. It’s a paradox that Gyllenhaal handles with this incredible, wide-eyed sincerity. She makes the "odd" feel completely logical.
The "Cure" Controversy
One thing that gets people fired up—even now—is the idea that Mr. Grey "cures" Lee’s self-harm. In the movie, he discovers her scars and commands her to never do it again.
And she stops.
Some critics back then (and now) found this problematic. They argued it suggests a woman needs a man to "fix" her mental health. But that’s a pretty surface-level reading.
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If you listen to how Gyllenhaal has talked about the role recently, she sees it as Lee finding a language for her pain. Instead of hurting herself in isolation, she’s engaging in a shared ritual with someone who understands her. It’s not about being "fixed." It’s about being understood.
Gyllenhaal once said in an interview with Film Independent that the story is like an "unsolvable puzzle." It doesn't fit into a black-and-white worldview. That’s why it lingers. It’s messy. It’s "dangerous," as she put it.
Does it Hold Up Post-#MeToo?
This is the big question. Could you make this today?
Director Steven Shainberg has been pretty vocal about the fact that he doubts it. Our cultural conversation around workplace power dynamics has changed so much since 2002. The idea of a boss spanking a secretary for a typo—even if she wants it—is a massive HR nightmare in the modern world.
But that’s kind of why the film is still vital. It exists in this heightened, almost fairytale-like bubble. The office isn't a real law firm; it’s a stage where two "broken" people are trying to build a world that fits them.
Lee Holloway isn't a victim of harassment. She’s a pioneer of her own desire.
The Legacy of the "Secretary" Style
We can't talk about this movie without talking about the look. The pussy-bow blouses. The pencil skirts. The way Gyllenhaal carries herself with that "bovine, contented smirk" (as The Guardian put it).
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She took the "secretary" trope—which has been a porn cliché for decades—and reclaimed it. She made it about agency.
How to Revisit the Film (And Why You Should)
If you’re going to watch it again, or see it for the first time, don't look at it as a "kink" movie. Look at it as a coming-of-age story.
Lee starts the movie as a girl who can't speak for herself. She ends it as a woman who has built a life on her own terms. It’s a weird life, sure. There are cockroaches involved. There’s a lot of red ink. But it’s hers.
Next Steps for the Cinephile:
- Compare it to the Source: Read Mary Gaitskill’s short story "Secretary." It’s much darker and lacks the "happily ever after" of the movie.
- Watch the Nuance: Pay attention to Gyllenhaal’s eyes in the final scene. Is she "subservient," or is she the one who finally won?
- Look for the Humor: This movie is actually a comedy. If you aren't laughing at the absurdity of the "four peas" scene, you're missing the point.
Ultimately, Maggie Gyllenhaal in Secretary gave us a character who refused to be "normal" and found happiness anyway. In a world that constantly tells us how we should behave and who we should love, that’s still a pretty revolutionary idea.
Don't just take the internet's word for it. Go back and watch her performance. It's a reminder that sometimes, the most "disturbed" people in the room are the only ones actually being honest with themselves.
Actionable Insight: If you're interested in how Gyllenhaal’s perspective on power and sex evolved, watch her work in The Deuce. She produced that series specifically to ensure the power dynamics were handled with the same nuance she brought to Lee Holloway two decades earlier.