History YMMV / HeadlessASleepyHollowStory

** [[spoiler: How much of Kat's behavior was genuine, and how much was her trying to lure Ichabod into becoming her sacrifice? She seems genuinely disinterested in him until he mentions he was taking care of his grandmother who recently passed away, which lines up with when she would have realized he had the makings of a perfect sacrifice and would start pretending to court him (checking in on him at work in the next episode). She may have genuinely been interested in helping with the Headless case as well, at least as a way to stay close to Ichabod and to help Matilda, since she had no idea the Horseman's head was keeping her alive. Alternatively, she could have purposely been luring them down dead ends to keep the group busy, such as the Cotton Van Tassel thing. It's hard to say for sure without knowing what Kat was like before her death.]]
*** WordOfStPaul from Creator/MaryKateWiles [[spoiler: indicates that Kat was considering using Ichabod even before she discovered his grandmother had passed away, but her decision was solidified by the end of that evening. However, Wiles also says she was genuinely excited to meet the Headless Horseman.]]
** [[spoiler: The same goes for Matilda. While she seems to genuinely want to help Headless, how much did she know about the details surrounding Kat and Baltus? She seemed to be involved in the poisoning plot, and was definitely involved in the resurrection. But did she purposely downplay Dr. Crayon's role in the cover-up by finding the checkbook and saying it was just for drugs, or was she unaware he was even involved? Did she know about Anne Tarry? Did she secretly ''want'' Baltus to get caught, or did Anne Tarry throw a wrench in things, making Matilda improvise and play along with the investigation, knowing the whole time?]]
*** WordOfStPaul indicates that [[spoiler: Matilda was at least told of the plan to use Ichabod as sacrifice during the Autumn Gala, before she decided to help Ichabod with Headless. According to Sinead Persaud, she was likely unaware of what happened to Anne Tarry, but knew Crayon was paid off.]]

** Diedrich Knickerbocker playing the narrator is appropriate, considering he was Washington Irving's DirectLineToTheAuthor in ''A History of New York'' and "Rip Van Winkle". In a sense, Creator/WashingtonIrving is narrating his own story.
*** [[spoiler: Jonathan Oldstyle was another pseudonym of Washington Irving's, making it appropriate that the character of the same name tries to replace Diedrich as bard.]]

*** WordOfStPaul from Mary Kate Wiles [[spoiler: indicates that Kat was considering using Ichabod even before she discovered his grandmother had passed away, but her decision was solidified by the end of that evening. However, Wiles also says she was genuinely excited to meet the Headless Horseman.]]

** With certain subsects of the TabletopGame/DungeonsAndDragons and Tabletop RPG community, particularly fans of ''WebVideo/CriticalRole'' and ''WebVideo/Dimension20'' due to Matthew Mercer, Krystina Arielle, and Ginny Di's involvement. The Kickstarter campaign even included a stretch goal to see the Shipwrecked crew play Dungeons & Dragons to cater to those intersecting fandoms, which was fulfilled.

** [[spoiler: How much of Kat's behavior was genuine, and how much was her trying to lure Ichabod into becoming her sacrifice? She seems genuinely disinterested in him until he mentions he was taking care of his grandmother who recently passed away, which lines up with when she would have realized he had the makings of a perfect sacrifice and would start pretending to court him (checking in on him at work in the next episode). She may have genuinely been interested in helping with the Headless case as well, at least as a way to stay close to Ichabod and to help Matilda, since she had no idea the Horseman's head was keeping her alive. Alternatively, she could have purposely been luring them down dead ends to keep the group busy, such as the Cotton Van Tassel thing. It's hard to say for sure without knowing what Kat was like before her death.]] Meanwhile, WordOfStPaul from Mary Kate Wiles [[spoiler: indicates that Kat was considering using Ichabod even before she discovered his grandmother had passed away, but her decision was solidified by the end of that evening.]]
** [[spoiler: The same goes for Matilda. While she seems to genuinely want to help Headless, how much did she know about the details surrounding Kat and Baltus? She seemed to be involved in the poisoning plot, and was definitely involved in the resurrection. But did she purposely downplay Dr. Crayon's role in the cover-up by finding the checkbook and saying it was just for drugs, or was she unaware he was even involved? Did she know about Anne Tarry? Did she secretly ''want'' Baltus to get caught, or did Anne Tarry throw a wrench in things, making Matilda improvise and play along with the investigation, knowing the whole time?]] WordOfStPaul indicates that [[spoiler: Matilda was at least told of the plan to use Ichabod as sacrifice during the Autumn Gala, before she decided to help Ichabod with Headless.]]

* SugarWiki/VisualEffectsOfAwesome: The effects for Matilda's spell are simply magical, especially for a fan-backed, independent production.
* WhatAnIdiot: [[spoiler: Baltus, as the incumbent mayor from a long legacy and a self-proclaimed town favorite, had a good chance of beating young, inexperienced teacher Rip fairly in an election. Instead, he goes to the trouble of trying to poison his competition ''at a party in his home'', which is already grounds for suspicion. But then, he doesn't even make sure Rip drinks the poison, leaving it open for someone else -- like his daughter -- to die instead. To top it off, he kills his assistant because he thought she overheard a conversation that would have given his crimes away. [[AllForNothing She never heard ''any'' of it]].]]

* SugarWiki/VisualEffectsOfAwesome: The effects for Matilda's spell are simply magical, especially for a fan-backed, independent production.

** [[spoiler: How much of Kat's behavior was genuine, and how much was her trying to lure Ichabod into becoming her sacrifice? She seems genuinely disinterested in him until he mentions he was taking care of his grandmother who recently passed away, which lines up with when she would have realized he had the makings of a perfect sacrifice and would start pretending to court him (checking in on him at work in the next episode). She may have genuinely been interested in helping with the Headless case as well, at least as a way to stay close to Ichabod and to help Matilda, since she had no idea the Horseman's head was keeping her alive. Alternatively, she could have purposely been luring them down dead ends to keep the group busy, such as the Cotton Van Tassel thing. It's hard to say for sure without knowing what Kat was like before her death.]]
** [[spoiler: The same goes for Matilda. While she seems to genuinely want to help Headless, how much did she know about the details surrounding Kat and Baltus? She seemed to be involved in the poisoning plot, and was definitely involved in the resurrection. But did she purposely downplay Dr. Crayon's role in the cover-up by finding the checkbook and saying it was just for drugs, or was she unaware he was even involved? Did she know about Anne Tarry? Did she secretly ''want'' Baltus to get caught, or did Anne Tarry throw a wrench in things, making Matilda improvise and play along with the investigation, knowing the whole time?]] Meanwhile, WordOfStPaul from Mary Kate Wiles [[spoiler: indicates that Kat was considering using Ichabod even before she discovered his grandmother had passed away, but her decision was solidified by the end of that evening. Matilda was told of the plan during the Autumn Gala.]]

** [[spoiler: The same goes for Matilda. While she seems to genuinely want to help Headless, how much did she know about the details surrounding Kat and Baltus? She seemed to be involved in the poisoning plot, and was definitely involved in the resurrection. But did she purposely downplay Dr. Crayon's role in the cover-up by finding the checkbook and saying it was just for drugs, or was she unaware he was even involved? Did she know about Anne Tarry? Did she secretly ''want'' Baltus to get caught, or did Anne Tarry throw a wrench in things, making Matilda improvise and play along with the investigation, knowing the whole time?]]
*** WordOfStPaul from Mary Kate Wiles [[spoiler: indicates that Kat was considering using Ichabod even before she discovered his grandmother had passed away, but her decision was solidified by the end of that evening. Matilda was told of the plan during the Autumn Gala.]]

* FunnyAneurysmMoment:
** Kat telling Ichabod to toss the enchanted wine because it's probably poisoned. [[spoiler: She would know, wouldn't she?]]
** Brom mentioning Kat throwing up at the previous Autumn Gala becomes a lot less funny [[spoiler: when it turns out she was dying from poison in that moment.]]

*** [[spoiler: The same goes for Matilda. While she seems to genuinely want to help Headless, how much did she know about the details surrounding Kat and Baltus? She seemed to be involved in the poisoning plot, and was definitely involved in the resurrection. But did she purposely downplay Dr. Crayon's role in the cover-up by finding the checkbook and saying it was just for drugs, or was she unaware he was even involved? Did she know about Anne Tarry? Did she secretly ''want'' Baltus to get caught, or did Anne Tarry throw a wrench in things, making Matilda improvise and play along with the investigation, knowing the whole time?]]

** Matilda Bishop, whose family has been persecuted for their magic, shares a last name with Bridget Bishop, one of the real victims of the Salem Witch Trials (though Bishop was her married name, and none of the Salem victims were actual witches -- witchcraft accusations were more of an excuse for others to gain land, power, and good standing).

* UnexpectedCharacter: [[spoiler: No one was expecting a brand new bard to appear at the top of the final episode, especially since Tom Lenk's appearance was not mentioned in the Kickstarter or series marketing.]]

* JerkassWoobie: [[spoiler: Kat's death was a complete accident, caused by her corrupt father trying to poison his rival. And this just after she discovered he had lied about her mother's death. While she goes to terrible lengths to stay alive, all sources indicate she was a good person and a good friend before this occurred.]]