WARNING: Unmarked spoilers up to Episode 9 below.
- Alternative Character Interpretation:
- After Brom and Matilda, who previously seemed physically repulsed by each other, are forced into a Marriage of Convenience to keep Judy from discovering the truth, Brom takes his new role as husband very seriously. He gets Matilda's groceries, frames their marriage certificate, and calls her "wifey", saying he loves her. Matilda seems to reciprocate a little, smiling at him, stealing his pants, and accidentally cuddling with him in their jail cell. While it has the makings of a Romantic Fake–Real Turn, how much "romance" or "sexual attraction" there actually is is debatable. But the two are still married and open up a shop together at the end of the series. Brom and Matilda also grew up together, and Brom listens when Matilda gives him a "Reason You Suck" Speech.
- 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. 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. Word of St. Paul from Mary Kate Wiles 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.
- 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? Word of St. Paul indicates that 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.
- Awesome Music:
- The theme music, and any time Diedrich sings his narration.
- "When Did You Have Time (To Make All This Slime?)"
from Episode 5 is incredibly catchy. - The heist music particularly stands out.
- Base-Breaking Character: Devlyn Versace. While some fans found her antics hilarious, others found her Bad Influencer personality off-putting.
- Friendly Fandoms:
- With Tin Can Brothers and Team Starkid fans, due to an overlap of actors.
- With certain subsects of the Dungeons & Dragons and Tabletop RPG community, particularly fans of Critical Role and Dimension 20 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.
- Genius Bonus:
- Diedrich Knickerbocker playing the narrator is appropriate, considering he was Washington Irving's Direct Line to the Author in A History of New York and "Rip Van Winkle". In a sense, Washington Irving is narrating his own story. 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.
- Officer Meinhof's name is a reference to the "Baader-Meinhof phenomenon", also known as frequency bias, where once you notice something once you start seeing it everywhere.
- 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 Sarah Bishop, who was accused but not condemned. She also shares a last name with Diana and Sarah Bishop from A Discovery of Witches, also witches descended from the Salem family of the same name. note
- Harsher in Hindsight:
- Kat telling Ichabod to toss the enchanted wine because it's probably poisoned. She would know, wouldn't she?
- Brom mentioning Kat throwing up at the previous Autumn Gala becomes a lot less funny when it turns out she was dying from poison in that moment.
- Jerkass Woobie:
- Devlyn may be a menace as an influencer, but her anxiety about the stunt that would indeed lead to her death is hard not to sympathize with.
- 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.
- While Baltus was a corrupt monster who is locked up, as he deserves, he also accidentally killed his daughter, the only family he has left. In the last shot of him in the Sleepy Hollow jail, he seems burdened by what he has done.
- Portmanteau Couple Name: Brom/Matilda is referred to by some as "Bromtilda".
- Stoic Woobie: Matilda lost her best friend to an accidental poisoning plot (one that she was implied to be a part of, making the situation worse) when they were both just 26 years old. While she finds a spell to save her, it only lasts for one year and involves sacrificing an innocent person's life force. She had to hide this for a whole year, with only Kat as a confidant.
- Visual Effects of Awesome: The effects for Matilda's spell are simply magical, especially for a fan-backed, independent production.
