Christina Ricci in Sleepy Hollow (1999)
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Credit: Warner Bros.

The Real Housewives of Sleepy Hollow: How the women really ran the town

Contributed by
Jan 30, 2020

Last year marked the twentieth anniversary of the Tim Burton thriller Sleepy Hollow, and it still feels like the film was released yesterday. The Johnny Depp-led film (which marked Burton's third collaboration with the actor) is a loose adaptation of the 1820 Washington Irving short story, "The Legend of Sleepy Hollow," which finds the town of Sleepy Hollow being terrorized by a headless horseman.

The gothic fantasy is mostly told through the lens of New York City constable Ichabod Crane (Depp), a peculiar yet bright man with a fascination with science, who is sent to the seemingly quiet town to solve the murder mystery. The movie shows us how several high-ranking men of Sleepy Hollow were a part of a grand conspiracy which was entangled with the release of the headless horseman, but if you take a closer look, you'll realize that the women were running the show.

Ichabod believes he will easily sniff out the killer and debunk the supernatural aspect of the slayings, he gets a little more than what he bargains for — first with a potential witchy love interest in Katrina Van Tassel (Christina Ricci) then with the villainess herself, Lady Van Tassel, Katrina's stepmother and overall mastermind, played wonderfully by Miranda Richardson. But these two smart, rich, and mystical women aren't the only ladies of Sleepy Hollow making the town quite exciting.

In fact, quite a few of the women of Sleepy Hollow give the town its heartbeat and soul with their almost Real Housewives parts to play in this murder mystery.

The Sneaky Social Climber:

Sleepy Hollow was filled with quite a few sneaky women, one of the sneakiest being the Widow Winship. This lady had quite a few secrets up her sleeve, the biggest of them all leading to her eternal silencing. This quaint quiet woman did what it seems few in Sleepy Hollow could do: bag one man, have him die on her, then snag another who was one of the most sought-after catches in the town.

From the looks of it, Widow Winnie was setting herself up with a sugar daddy and she proceeded to do what many only attempt: she got pregnant, and secured the bag!

While we'll never know if this was really for love or money, what I will refuse to think about is the sexy time she had to endure with Peter Van Garrett and how much she had to do to get knocked up. All I can assume, however, is it must've been good since she got herself penciled into that man's will and got her step-son in such a fervor over being pushed aside as heir of the estate. Drama!

Had she survived, the newly-dubbed Mrs. Van Garrett would've been the woman running things in Sleepy Hollow, but her new glamorous life got cut short before she could dance it out to Sheila E.

The Messy Gossiper

Credit: Warner Bros.

The saying goes that "silence is golden," and "real Gs move in silence." They are right, and the Widow Winship was a real G for putting that loving on old rich men to get a come-up in the sleepy town of Sleepy Hollow. But, Beth Killian wasn't going to be afforded those luxuries as a midwife.

So as the person in the town bringing babies into the world, she was also brewing all the spicy tea leaves her pot and spilling it almost as fast as the placenta she was pulling.

I'm pretty sure Beth knew all the secrets in town: she probably knew which women were cheating on their husbands (and slipping them holistic abortions), which women were trying to keep from having babies with their crappy husbands, and which women were sleeping with other people's husbands.

The only problem with getting all that lovely intrigue in a small town is the desire to spill it to whoever would listen, including other rich women with axes to grind. Was Beth wrong for dishing the dirt in front of her husband and child? Absolutely not. I'm pretty sure her husband was the type to be all, "Oh, Beth" when she started gossiping, but alas, the horseman didn't know, nor did he care. Sadly, her life was cut short before she could tell all the tea.

The Low-Key Side Piece

Credit: Warner Bros.

Though glanced over, another woman with a part to play in this web of deceit was the servant girl Sarah. Another one moving in silence (mostly because she had no speaking lines), Sarah was just as integral to the murder mystery, which makes her a welcomed lady to the table of Sleepy Hollow Housewives.

She wasn't a wife, nor was she a proper girlfriend, but she was a side piece to Doctor Lancaster and that makes her just as important as everyone else. Everyone knows mistresses add a little something extra, and so did she. It wasn't implicitly said, but I'm pretty sure her relationship with the doctor was secret for two main reasons: she was a servant, making her a lower-class citizen, and then, of course, a doctor in Sleepy Hollow would not be walking around unmarried.

In the group, Sarah gets the least amount of respect only because her relationship isn't helping her in any real way aside from getting to bed a prominent man in hopes she could be the next Widow Winship, but that doesn't mean she doesn't have a little juice. Her relationship with Doc Lancaster ultimately kept him alive as a bargaining chip for his knowledge of the Widow's pregnancy. It would've been interesting to know if Sarah knew about it, because not only would she have an affair under her hat, but insider knowledge about Widow Winship's baby and marriage.

The Tell-It-Like-It-is

Probably the only person who was willing to tell the truth, no matter how ugly, was the shunned witch of the woods. In his quest for answers, Ichabod sees the witch at the edge of the woods, who matter-of-factly told him the Headless Horseman was real and had been killing people. She even complained that he and his horse clamoring back and forth were keeping her up at night (and I bet he was also funking up the forest with all those dead people's heads he was lugging around, at that).

Unlike the other women in town, the Witch didn't need a man, although she did have a connection to "the other." Why have a man when you can be possessed by an all-knowing spirit? While she told it like it was, there was one thing she didn't spill the beans on — the identity behind the murder plot, probably because the mastermind was none other than Lady Van Tassel, her twin sister! (Plot twist!) She could've blabbed that bit of info, but kept it to herself in hopes what little truths she revealed were just enough.

The Goody-Good Girl

Credit: Warner Bros.

There's always a little miss "Goody Two Shoes" and it came in the form of the second most powerful woman in the town, Katrina Van Tassel. Her father was wealthy, she was an only child in her family, and was sought after by the strongest, bravest man in town, Brom Van Brunt. Because life had been handed to her on a silver spoon, she was both innocent and ditzy due to her healthy helping of privilege.

Katrina becomes a prime suspect in the series of deaths in Sleepy Hollow as she's also in line to inherit the Van Garrett fortune in the event of her father's death, but her sweeter-than-saccharine persona speaks to how distant her thoughts are on the entire episode. Further, when you've got so much money and never had to want for a thing in your life, would you really be scared of having your head cut off? Not in the slightest.

This combination of sweet and sheltered also lends itself to her being turned from her potential intended Brom by Ichabod's weird New York City demeanor and disdain for the mystical. Though Katrina challenges him on the ideals of magic being as natural as everything else, their opposites attract and they strike up an unspoken romance. In a matter of days, she declares her attraction to Icky and forgets about Brom. Doesn't even shed a tear for the man when he's sliced and diced like a carrot in a slap chop machine.

In this group of Housewives, Katrina is the sweet albeit simple beauty who has money, may have a secret fetish, aims to see the best in everyone and wouldn't be able to smell a gold-digger a mile away. The one that everyone says "bless your heart" to when speaking in a conversation that's clearly above her head. Oh, Katrina.

The HBIC

Credit: Warner Bros.

Tying all the women (and persons of interest) together is the HBIC herself, Lady Van Tassel née Archer. As I previously mentioned, she is the villainess of the film and is quite possibly the smartest, sneakiest, and most treacherous person in Sleepy Hollow. And she did while still wearing a corset and not fainting once.

Lady Van Tassel is the ultimate hustler and is quite possibly the NeNe Leakes of Sleepy Hollow. She knew all the dirt, where to dig it, and when to plant a seed to let it grow. She's the epicenter of all the drama, bringing all these women together, while simultaneously instigating every stitch of confusion to tear them all down and apart.

Coming from humble beginnings as a twin outcasted in the woods, Lady Van Tassel climbed her way up in the world to maneuver her way into revenge and a fortune by:

  1. Promising her soul to the devil if the Horseman would avenge her
  2. Assimilating into the town that shunned her family as a nurse
  3. Possibly killing the first Lady Van Tassel (Katrina's mother), and then becoming a wife to the second wealthiest man in town
  4. Stirring up drama between the conspirators who knew of the Van Garrett family secret
  5. Using the horseman to kill all witnesses that would lead back to her
  6. Killing any and everyone that she had to cover her tracks
  7. Faking her death to then kill the sole inheritor and have it all

Without Mrs. Van Tassel, life in Sleepy Hollow wouldn't be as exciting to watch or even care about. She played the part of the demure wife, the sultry adulteress (with some kinky knife play in the woods to boot), and then finally the badass evil-doer who was ridiculous unapologetic.

Hey, when it comes to being a Housewife, someone's gotta play the "bad guy," and Lady VT was all about assuming that role — and she murdered it. Pun intended.

And so, the women of Sleepy Hollow did run this movie after all. We may want to consider a new retitling: The Real Housewives of Sleepy Hollow, with each lady holding a small pumpkin in the opening credits sequence.

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