Murder She Wrote: Night Of The Headless Horseman

I first watched Murder, She Wrote when it aired on television and had seen more than a single season before reaching my tenth birthday. Most episodes, though enjoyable, are not all that memorable, but some really stick with me. One such episode is The Night of the Headless Horseman.

It’s an episode in the middle of the third season and borrows heavily, as the title implies, from The Legend of Sleepy Hollow. It’s a very interesting episode and I’m going to discuss its plot and characterization, but first I’m going to give a brief recap of the plot in the reader has not watched this episode recently.

We begin by being introduced to Dorian, a tall, gaunt poetry teacher in a rural boarding school/horse riding academy. He is very much Ichabod Crane. He is reading a poem to the lady he’s courting, Sarah, who is the daughter of the wealthy owner of the school/riding academy. She, too, is very much Katrina Van Tassel (Ichabod’s love interest, if you don’t remember).

The school is set in the south, at least to the degree that the actors can do southern accents (it varies), so we even have the plot element of Dorian being a Yankee outsider (in The Legend of Sleepy Hollow, Sleepy Hollow it was a Dutch settlement). Further borrowing from the famous story, as Dorian walks home, he is comes to a covered bridge:

And then, to pay off the title, out of nowhere a headless horseman carrying a jack-o-lantern rides up.

The rider chases Dorian onto the bridge and throws the jack-o-lantern at him. As the rider rides off, Dorian shakes his fist and exclaims, “Damn you, Nate Finley!”

So far, we have a remarkable homage to The Legend of Sleepy Hollow. We’re only about three minutes in, however, and things will begin to diverge, as they must, when Jessica arrives. Speaking of which…

The scene now changes to Jessica arriving from Cabot Cove via the train; Nate picks her up at the station. They begin to catch up, then in what is ostensibly an explanation of what Dorian is doing at the prestigious Wenton Academy (the school/riding academy), we get some obviously important backstory.

Dorian has the job because over the summer the previous poetry teacher, a beautiful young woman named Gretchen, died under mysterious circumstances. The daughter of the Academy’s stable master, she drowned in the river, and—hint, hint—rumor has it that there was a man with her who was the one behind the wheel. If you can’t guess that the earlier mystery will drive the murder we haven’t seen in this episode, you clearly haven’t been watching Murder, She Wrote for long. They do work it in as backstory and gossip well enough that you can feel clever for spotting it, though.

Next, Dr. Penn Walker, the town dentist, shows up:

In this encounter we learn two major things:

  1. The doctor has a strong interest in jewelry; it’s a hobby of his.
  2. He thinks that Jessica is Dorian’s mother.

On the car ride from the train station, Dorian tries to stall Jessica with conversation, in which we learn that the good doctor was engaged to Gretchen, the poetry teacher who died under mysterious circumstances. Also, he was in Europe when it happened. (This simultaneously clears the doctor of being the man behind the wheel and also sets him up with a very strong revenge motive.)

After these important details, Jessica forces Dorian to come clean, and he admits that he’s fallen in love but his intended fiancé’s father has a fixation with pedigrees and so, being an orphan, he wanted to present at least one parent and so lied that Jessica is his mother. This conversation is interrupted by Nate Finley, who rides his horse in front of their car for no reason, then laughs at them.

Clearly, we’re not meant to feel sorry for him when he turns up dead.

(Nate Finley does match the character of Abraham Van Brunt, in being the other suitor for Sarah’s hand and a far better physical specimen, though less socially adept. His character does depart from Van Brunt’s, though, as we’ll see.)

Jessica and Dorian get to the school where some awkwardness ensues as Jessica isn’t sure whether to play along with the lie of being Dorian’s mother. We then get introduced to a trio of boys who play a prank on the stablemaster (driving the horses off, out of the stable). The stablemaster appears to be German; he is named Van Stottard and has a thick German accent, anyway.

Nate Finley happens to be around and threatens the stablemaster that he will find a new stablemaster if the current one cannot keep control of the horses. It’s a noble effort on the part of the writers to distract from the characters just introduced by highlighting what a bad guy Nate Finley is, but one of the problems that Murder, She Wrote writers labor under is that they don’t have the budget for unimportant characters. That said, they do at least have the freedom to make characters important for surprising reasons, so we don’t really know what part the boys play in this.

Dorian accuses Nate Finley of being the headless horseman, which he doesn’t deny. Finley then rides off.

In the next scene, we get the owner of the school telling the headmistress that he wants Nate Finley fired.

This is an unusual move for a television show; ordinarily bullies on TV have the unconditional support of authority figures. The headmistress tells him to calm down; he knows as well as she does that Nate Finley is as good as they come in the saddle, and their riding program is, for some reason, of the utmost importance to the school. Why, is never explained. Even in the 1980s it was a bit of a stretch that wealthy parents would choose to send their children to a boarding school primarily on the basis of its riding program.

The headmistress surmises that the owner is afraid for his daughter, and suggests he should look out for the new English teacher instead. Some more introductions are made and the stablemaster barges in holding all three boys we met earlier. He charges them with committing pranks and they do not deny it; the headmistress says that she will deal with them later.

That night, the headmistress interrupts Nate Finley saddling up his horse to tell him to stay away from the owner’s daughter.

“I want you to stay away from Edwin’s daughter. Satisfy your needs elsewhere.”
“Is that an order, or an offer?”

This dialog is a bit odd in that we learn moments later that the two were involved with each other; she threatens to fire him if he doesn’t stay away from the owner’s daughter and he threatens to tell the owner that they were together. Either way, though, Nate Finley clearly deserves the murdering he’s about to receive, and I suppose that this scene serves to establish the headmistress as a possible culprit.

The next scene moves to a restaurant in which the wait staff dress up in period costume for some reason, and we meet the waittress, Bobbie.

She seems to be set up almost as a love interest for Dorian, except that he never really pays any attention to her. The dentist comes in and sits down with Jessica and Dorian. He notices Bobbie’s neclace, and asks where she got it. She replies, “Nate Finley, Doc. Guess he figures it will get him somewhere, which it won’t.” And before anyone else has a chance to speak, Nate Finley walks into the bar. Jessica warns Dorian not to start anything, but in vain, because Finley starts it.

Finley tries to warn Dorian off of Sarah, but Dorian punches him in the mouth. They fight for a while, and Dorian gets shoved against the wall where he knocks down an old saber. He picks it up, as several of Nate Finley’s friends are standing around him.

If you think that there’s any chance that Dorian isn’t holding the murder weapon, you haven’t seen Murder, She Wrote before. Nothing happens here, though, because the Sheriff—who had been conveniently on his way to dinner, I suppose—breaks up the fight.

The fight over, Nate mentions that he thinks he broke a tooth, and a raw nerve in his mouth being exposed, he does the logical thing and asks for a stiff drink from the bartender.

Dorian leaves. As Jessica leaves, she notices the leader of the three trouble-making students feeding Nate Finley’s horse. She says hello to him, but he just walks off.

Dorian goes to Sarah’s house, but no one is home. On his way back, right before the covered bridge, Nate Finley’s friends show up in a yellow pickup truck. He asks them for a ride back to the academy but instead they give him the murder weapon.

They drive off. Dorian only makes it a few more steps before the headless horseman rides again. Dorian tries to defend himself with the sabre…

…but only gets knocked down. His head hits a rock and he falls unconscious.

The next day the stablemaster and headmistress are concerned about Nate Finley’s horse. He had been ridden hard but not cleaned. The sweat has dried into his fur. (This is a problem for horses because the tack the wear—bridle, saddle, etc—will tend to rub the sweat into their skin, causing irritation. Any good horseman will always clean his horse after riding him, for the horse’s sake.) The attentive viewer will infer that Nate Finley has finally been murdered, though the characters don’t catch on just yet. This does yield an interesting problem for the viewer, though, since as far as we know Nate Finley was the headless horseman, and the headless horseman was the last person we saw alive.

Dorian stumbles into the stable and announces his intention to get even with Nate Finley. No one knows where Finley is, though.

Jessica, out on her morning bike ride, runs into the police who have found Nate Finley’s body. The Sheriff asks if Jessica knows where “her son” is, but she doesn’t. No sooner has she said this than a car pulls up with the headmistress and Dorian in it. Dorian launches into a complaint at the Sheriff about how Nate Finley had attacked him the night before. The Sheriff is interested, and asks questions that don’t seem entirely related. Jessica puts two and two together and realizes that Nate Finley has been killed. They see the body under a tarp, or possibly a black cloak. Jessica notices something about the feet:

The boots are on the wrong feet! I’m not giving anything away here, at least by more than a few seconds, as Jessica starts pointing this out to anyone who will listen almost immediately.

It is revealed that Nate Finley was decapitated, so the Sheriff arrests Dorian as having recently threatened Nate Finley with a saber. Curiously, it never occurs to anyone to ask whether a wall decoration at a restaurant was actually sharp. It’s actually pretty rare for wall decorations to be kept in fighting condition. I suppose we’re meant to assume that it was, since the saber is later referred to as “bloody”.

Jessica argues with the Sheriff, pointing out problems with his case, and finishes with the fact that Dorian has sworn that he didn’t do it. That’s supposed to hold weight because Dorian doesn’t lie. When the Sheriff points out that of course she thinks that, being his mother, Jessica accidentally admits that she’s not his mother. As he puts Dorian into the jail cell, he tells Jessica that it’s encouraging to hear that Dorian doesn’t lie.

In the next scene, Jessica and Dorian talk over the situation.

A little bit is added to what we already know. Dorian saw the owner of the school driving off from his house in a hurry. When Jessica talks to Sarah about it, Sarah claims to be the one who drove off, but is obviously lying. The owner comes out and admits to being the one who nearly ran Dorian over. He had gotten an anonymous note that the headmistress was embezzling funds, so he waited until his daughter was asleep and drove off in a hurry to confront her. He did, she denied it, the owner said he would retain an independent auditor, then returned home. (The owner also asks her to tell Dorian to stay away from his daughter or there would be another killing.)

Back at the academy, Jessica runs into one of the three boys, but he runs off when he’s questioned. She runs into the stablemaster, but he refuses to answer questions, except to say that he had no reason to kill Finley but there are others who did. He walks off when Jessica asks if he meant the headmistress, perhaps. So, on to the headmistress.

We get a small scene of the three boys in a secret room at the top of the stables, where one says that they need to tell someone, and the ringleader says that they won’t tell anyone. What won’t be told is, of course, suggestively left off.

When Jessica talks with the headmistress, she says that there is a problem but she’s not the thief. Jessica wonders who knew about the problem and the headmistress gets defensive, asking if she’s trying to implicate her in Nate Finley’s death. Jessica deflects by asking if she’s seen the note.

The spelling is so bad it could even be written by a German! (The stablemaster, you will recall, is German.)

The next scene takes place at the restaurant; it turns out that Dorian has been released from jail, though whether on bail or what is unclear. The waitress, Bobbie, comes over and tells Dorian that she believes that he’s innocent, but if he did kill Finley she could totally understand. It comes out that Bobbie saw Nate riding through town with his black cloak and black floppy hat pulled down low. This was at 11:30, but the Sheriff said that Nate was at the restaurant until 10:30. What happened in that missing hour?

Dorian then breaks a took on an olive, which necessitates a trip to the dentist.

It turns out that he only loosened a cap, which the dentist can re-cement for him. Jessica asks if the doc noticed anything odd about Nate’s dress last night, as he was found with his boots on the wrong feet. The doc observed it would be hard to walk like that; perhaps he had gotten undressed and re-dressed in a hurry. He heard Nate did that quite often, usually with an irate husband in the vicinity.

Jessica then notices a picture on the Dentist’s bureau.

(The inscription reads, “Love Forever, Gretchen”. It’s curious how often people in TV murder mysteries give each other signed headshots as keepsakes.)

That night we see a fight between the owner and his daughter, then one of the three boys spies the stablemaster burying something in a horse stall.

The next morning Jessica is with the headmistress, who tells her that it is the stablemaster who stole the money. Jessica goes to talk to him, but can’t find him. She does, however, hear the boys in their secret loft in the stables, and goes to investigate. She uses the secret knock she heard earlier, then as she opens the door tells them, “When I was a little girl, if you knew the secret knock it entitled you to enter.”

She talks to the boys and they admit to having been the headless horsemen who harassed Dorian the first time, but had nothing to do with the second time. Also, one of them saw the stablemaster bury something (he took to be Nate’s head) in a sack.

In the next scene the Sheriff has his deputy digging up the spot. As the Sheriff goes to open the box that had been buried, Jessica shields the boys from the terrible sight, but it turns out that the box contains only money. The stablemaster had been embezzling money in order to pay a detective to investigate the death of his daughter. He hands over the file that the detective had assembled. There was nothing of value in it, but for some reason it did include another headshot of Gretchen.

Luckily for Jessica, this time Gretchen was wearing a necklace. Jessica recognizes it and solves the puzzle.

In the next scene the dentist comes to visit Jessica in the restaurant which hasn’t yet opened. Dorian told him that Jessica wanted to talk to him.

Come into my parlor, said the spider to the fly.

This can mean only one thing. If you hadn’t figured it out from the clues or by simple process of elimination, the doctor is the killer.

She realized that the necklace Gretchen was wearing in the headshot was the same necklace that Nate Finley had given to Bobbie. The dentist, who makes jewelry as a hobby, had made it and given it to Gretchen and recognized it when it was on Bobbie’s neck. He couldn’t help but know what it meant—that Nate Finley had been the man with Gretchen when she died. (Presumably he snatched the necklace off of her neck before swimming to safety and leaving her to drown.)

Finley had complained of a busted tooth after his altercation with Dorian, and presumably went to a dentist about it. A lot of things in the case didn’t make sense, like the severed head, unless there was something about the head that would instantly point to the killer, such as fresh dental work.

The dentist broke down and told Jessica what happened. Finley did come, and, seeing the picture of Gretchen, started laughing and telling the dentist all about how he had been drunk and drove the car into a lake and abandoned Gretchen to die. Finley was apparently very drunk, because in the re-enactment, he found the whole thing very funny.

At his bragging about leaving Gretchen to die, something snapped in the dentist and he jammed a pick into Nate’s neck. He died quickly. The dentist then figured that he had to make it seem like Nate died elsewhere, so he stripped Nate, put on the clothes, and rode Nate’s horse out of town, making a lot of noise to ensure he would be noticed. He ran into Dorian and knocked him out, then got the idea to frame Dorian using the saber Dorian was holding. The rest, we already know.


The use of the Legend of Sleepy Hollow setting is definitely very interesting, but it faded pretty quickly. Really, after the first few minutes the only thing that was left was the headless horseman. To some degree this was inevitable as they made the horseman the victim, rather than the murderer. That is simply unrelated to the original story.

Now, variation from Sleepy Hollow was inevitable, since that was not a murder mystery. However, I can’t help but think that they didn’t really make as much use of the headless horseman as they could have. First, I’d like to explain why, then I’d like to talk about how they could have made more use of it.

The big problem that the writers had was that in the original story, Ichabod Crane was not the hero. He was wooing Katrina Van Tassel for her money, not out of love. Worse, Katrina didn’t love him, either. The original story isn’t explicit, but it is very strongly hinted that Ichabod proposed marriage to her and she rejected him. It is further implied that her reason for encouraging Ichabod was to stoke the interest, by jealousy, of Abraham Van Blunt. Van Blunt is not as smart as Ichabod, nor as socially graceful, but he was the man Katrina wanted. This, coupled with Ichabod’s mean motive for wooing Katrina really make him a thoroughly unsympathetic character. So right off the bat, making Dorian the underdog-hero of the story creates a lot of distance from the original.

Further, the structure of the story just isn’t paralleled, because the headless horseman (a decapitated Hessian soldier) was a local legend and Ichabod Crane was an extremely superstitious man. Van Blunt used the legend and Ichabod’s cowardice and superstition to drive him out of town. Indeed, for all of his quicker wits, Ichabod was in a way the intellectual inferior for being superstitious. It’s an evocative story in which a pretentious man was shown up for what he truly was. Except for the way that Dorian is a bit full of himself—which is portrayed in a sympathetic way by the writers—none of this comes forward.

To now consider how it could have been used: the more traditional approach to dealing with this sort of thing is for the murderer to try to use the legend or story which everyone knows and to use it to divert suspicion onto the person who most fits the villain of the original legend or story.

If this were a Scooby Doo episode, then someone could pretend to be the headless horseman in order to try to get people to believe that it was actually the headless horseman who committed the crime. Since this isn’t Scooby Doo, we would need the Ichabod Crane figure to be the victim and the Van Blunt character to be the suspect.

Now, obviously the setup in this episode is nothing like that, but that’s why the episode didn’t really live up to its first few minutes. In fact, they stuck to it too closely at the time of the murder—it really makes no sense for the victim to have knocked the killer unconscious immediately prior to his own murder.

There is, admittedly, something interesting about the idea of the headless horseman turning up to be really headless, but I don’t think that idea can really be made to last any longer than the words necessary to describe it.

The other typical way to handle something like this would be to have someone who rides as the headless horseman then try to frame the victim as the headless horseman, and frame someone else for the murder, as revenge.

This approach would still entail a large divergence from the original story, but it would at least keep up the appearance of being related to the original story, and on purpose. The killer would need to benefit from getting rid of both the victim and the person he frames for the death, of course. This motive would be obscured behind the bigger grudge between the victim and the one framed.

This approach could have been made to fit much better with the setup, though it would need to be the horse instructor who was Jessica’s friend, not the Ichabod character. The doctor, instead of seeking revenge for his dead (unfaithful) fiancé, would be in love with Sarah, too. The doctor would have ridden as the headless horseman, possibly two or three times, then would have killed the Ichabod character. The riding instructor friend of Jessica would then come under strong suspicion of the crime, and she would need to clear his name. The gullible Sheriff could actively point to the legend of sleepy hollow, and how it pointed to the riding friend as the guilty party. If they wanted, they could even have made the parallel stronger by making the death accidental, with the doctor only meaning to scare off the Ichabod character and instead frightening the coward into jumping into the river, where he drowned because he couldn’t swim, or the river was too fast, or whatever. His original plan could have been to just frame the riding instructor for being mean to the poet, and using that to make Sarah dislike him as a suitor, with the homicide and subsequent framing of the riding instructor for murder being accidental.

All that said, this is a very memorable episode, owing largely to the first few minutes and how well they remind one of The Legend of Sleepy Hollow. However much they could have done better, it is a testament to the power of being evocative that this episode sticks with one.

Give people something to remember you by, and they will probably remember you.

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