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1[[foldercontrol]]
2!Main Characters
3
4[[folder: Ichabod Crane]]
5!! Ichabod Crane
6[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31200_pm_8.png]]
7 [[caption-width-right:300:''He’s quiet, and cautious, and really quite plain / And he goes by the name of sir Ichabod Crane.'']]
8!!!'''Portrayed by:''' Sean Persaud
9-> ''“You're going to help me pay my rent? If I help you find your head. Sure! Why not. Centuries-old German soldier needs my help. Could kill me at any time. First day of work in a new town. Mean landlady. Cute girl at the not-a-drugstore. This is a lot.”''
10
11
12The new Sleepy Hollow middle school science teacher from Hartford, CT, who desperately needs a roommate to help pay his rent.
13----
14* AdaptationalBackstoryChange: Prior to moving to Sleepy Hollow, he took care of his grandmother until her passing. He was also born in Sleepy Hollow, and was sent to live with said grandmother after his parents died.
15* AdaptationalJobChange: A very slight one, as he goes from general schoolmaster to specifically teaching science.
16* AdaptationalPersonalityChange: Ichabod in the original story, while the schoolmaster, had a strong belief in the supernatural (which was fairly common in the 1800s, when the story took place). In the web series he is a skeptical science teacher who is forced to believe when faced with the weirdness of the town.
17* ButtMonkey: Gets lost in the cursed bog and put down by others who don't like his jokes, and must assist the Headless Horseman if he wants to keep his lodgings. [[spoiler: This is especially true in Episode 5 when Brom gets him stuck with Devlyn Versace as his counsel -- she pantses him ''and'' slimes him on livestream]].
18* CantGetAwayWithNothing: While Matilda, Brom, and the Babes are able to easily dig up heads for Matilda's spell, Ichabod's one time in the Sleepy Hollow graveyard after hours (where he didn't even dig up anything) gets him sent to court. Justified, since Ichabod is new to town while Brom and the Babes are implied to have been dodging the local law enforcement for years.
19* CoolTeacher: Despite his timid nerdiness, he was the star teacher back in Hartford and manages to impress Christa and Brom by demonstrating a chemical reaction of lemon juice and heat.
20* ConnectedAllAlong: [[spoiler: Ichabod's ancestor was the witch who helped create the Horseman in the first place.]]
21* CowardlyLion: In the finale, [[spoiler: Ichabod finds courage he didn't even know he had, restoring Henrietta and Rip Van Winkle and redeeming the Storms name. He receives Henrietta's sword as thanks.]]
22* FamilyHonor: [[spoiler: Inadvertently. Henrietta says he was drawn back to Sleepy Hollow in order to restore the Storms family honor by finding the courage to break the curse his ancestor cast on Henrietta generations before.]]
23* HiddenDepths: Once took a class on pressure points, which he remembered enough to get out of Brom's headlock. He also adeptly puts together the clues about the Headless Horseman to find the missing head.
24* InUniverseNickname: Kat calls him "Absent Glory", based on the meaning of his first name (see MeaningfulName below) which they discussed in their first conversation. Brom calls him "Ick" and "Icky".
25* MeaningfulName: Discussed. His first name means "Absent Glory", though he tries to see it as a good thing. [[spoiler: After reuniting Henrietta with her head and restoring the Storms' family honor, he receives Henrietta's sword, named "Glory".]]
26* NerdyInhaler: Keeps one in a fake book by his bed, and is seen taking a hit from it when overwhelmed.
27* OrphansPlotTrinket: Carries around a necklace from his late grandmother, with the same symbol as the one on the Horseman's sword.
28* SecretLegacy: [[spoiler: Ichabod's ancestor was the school teacher and witch Anneke Storms, who changed her children's last name as penance for cursing Henrietta Hudson. He is the means by which Anneke makes amends to Henrietta.]]
29* SeekerArchetype: He comes to Sleepy Hollow seeking answers about his family. The further he gets into the Headless mystery, the more he wants to know the truth, and starts putting the pieces together in episodes 7-9.
30* SicklyNeuroticGeek: Easily spooked, asthmatic, and allergic to pretty much all animals and certain kinds of pollen. Also a great teacher and really into science and astronomy.
31* TheStraightMan: To much of the wackier cast members, particularly the Horseman's heads, often LeaningOnTheFourthWall as he comments on the insanity around him.
32[[/folder]]
33[[folder: Kat Van Tassel]]
34!! Katrina "Kat" Van Tassel
35[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31211_pm_9.png]]
36 [[caption-width-right:300:''Kat Van Tassel, the mayor’s lovely daughter / She’s sassy and bright and against animal slaughter.'']]
37!!!'''Portrayed by:''' Creator/MaryKateWiles
38->''“So here I am, pursuing my dreams of serving beer at not-a-drugstore.”''
39
40
41The mayor's daughter and a cashier at Colonial Drugs 'N' Stuff.
42----
43* AgentScully: Doesn't believe anything weird is going on in town, chalking Rip Van Winkle's disappearance to him moving away. [[spoiler: This turns out to be a subterfuge -- she knows full well what happened to Rip Van Winkle, since it's her fault he's missing.]]
44* ArbitrarySkepticism: Despite her best friend being a witch, she doesn't believe Brom's supernatural tales. Justified, since Brom is not the most reliable source of information. WordOfGod indicates this was a reaction to her mother's death. Her mother was more of an AgentMulder, who wrote all about local legends, but died in disgrace because no one would publish her final book. Kat became more of a skeptic in the aftermath. This is subverted once she discovers the Horseman is real.
45* BrokenBird: Kat's past, from her dead mom to her dropping out of school to return to her small town, speaks to this. She's particularly become skeptical of local legends since her mom's death. [[spoiler: Even more so when it turns out she's technically been dead for a year and needs to find a sacrifice before the end of the month to keep living, coldly killing multiple characters in the finale.]]
46* ColorMotif: Each of her outfits incorporates shades of white, gray, and/or black. She also frequently wears black-and-white stripes, as a MythologyGag to the Katrina Van Tassel from ''Film/SleepyHollow1999''.
47* EveryoneLovesBlondes: Kat is blonde. Not only do Brom and Ichabod both have crushes on her, but she is best friends with Matilda, who doesn't seem to like anyone else.
48* HotWind: Kat is introduced with one.
49* LittleMissSnarker: Many examples.
50--> '''Ichabod:''' Mayor Van Tassel is your dad?
51--> '''Kat:''' That's what he tells me.
52* MissingMom: Kat's mom died when she was 10 years old. [[spoiler: Later it's revealed she actually went missing and became The Woman in White.]]
53* TheOneThatGotAway: For Brom. They used to date more than ten years ago, but while Kat has moved on, Brom still wants her [[spoiler: until he accidentally marries Matilda]].
54* RichBoredom: Averted -- despite being the mayor's daughter, she dropped out of college and is working at the local not-a-drugstore. This is why Ichabod is so surprised to find out she's the mayor's daughter after meeting her at the store.
55* SmallTownBoredom: Thinks Sleepy Hollow is boring and can't understand why anyone would want to move there.
56* SugarAndIcePersonality: While she initially doesn't seem to pay Ichabod much attention, she shows signs of interest and concern for him, such as stopping by the school in Episode 2 to make sure his first day was going okay. [[spoiler: This turns out to be an act.]]
57[[/folder]]
58[[folder: The Headless Horseman]]
59!! The Headless Horseman/ "Headless"
60[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31142_pm_0.png]]
61 [[caption-width-right:300:''Just when you think you’re safe asleep in your bed / You may come ‘cross a fellow who’s lost his head.'']]
62!!!'''Portrayed by:''' Tom [=DeTrinis=]
63-> ''“He’s the ultimate shark. Decapitated in battle, he wanders these woods at night, unable to pass on until he is reunited with his head.”''
64
65
66A decapitated spirit, wandering the Sleepy Hollow woods in search of his head. He agrees to help Ichabod pay rent if Ichabod finds his head. (For tropes pertaining to the Horseman's true identity, see the entry under Horseman's Heads.)
67----
68* AdaptationalNiceGuy: Unlike other versions of the story where the Horseman is the antagonist, in this version he just wants his head back and agrees to help Ichabod pay his rent in exchange. He even pats Ichabod on the back and hugs him.
69* AffectionateGestureToTheNose: Gives one to Ichabod after he agrees to help him.
70* DeadToBeginWith: The Horseman died centuries ago, but his body is roaming around. However, the longer he is separated from his head, to more memories he loses.
71* GhostAmnesia: A little more flesh than a typical ghost, but the longer he goes without his head, the more he forgets.
72* HeadlessHorseman: Based on the TropeCodifier.
73* InUniverseNickname: "Headless".
74* TheSpeechless: Due to lacking a head, he can't speak, only communicating in gestures that Ichabod can somehow understand.
75* UnPerson: The curse that turned him into the Horseman erased his memory and most aspects of his true identity, [[spoiler: including [[SamusIsAGirl their gender]].]]
76[[/folder]]
77[[folder: Brom Bones]]
78!! Abraham "Brom Bones" Van Brunt
79[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31221_pm_1.png]]
80 [[caption-width-right:300:''Burly Brom Bones teaches P.E. at school / Being dope, chill, and woke is this bro’s only rule'']]
81
82!!!'''Portrayed by:''' Gabe Greenspan
83-> ''“I’ve got extra bones. It’s a genetic thing, it’s no big deal. It’s honestly? Pretty cool.”''
84
85
86The middle school gym teacher and self-proclaimed local "historian" on all things spooky.
87----
88* AdaptationalNiceGuy: He's more friendly towards Ichabod in this version, though there are traces of JerkJock behavior, and his jealousy increases the more Ichabod and Kat hang out. He's also less of a misogynist in general and is against hazing.
89* AgentMulder: Believes in all of the local legends.
90* BlatantLies: Says he doesn't get scared, soon after getting startled by a skeleton.
91* BrainlessBeauty: A muscular hunk who struggled when trying to substitute for the science teacher during the past year and thinks "history" means "fun stories that prove I'm right".
92* CrazyJealousGuy: ZigZagged. Starts wheezing when he realizes Ichabod and Kat are hanging out together, assuming they're on a date, and both outs the Horseman in front of Kat in hopes of scaring her off and gives Ichabod the wrong head so he'll get sent to jail. This later becomes a backfired trope when Matilda gets Brom to see his jealousy has reverted him to his high school bully self again, and damaged his relationship with Ichabod. He makes amends, and [[spoiler: seems to let go of his crush on Kat altogether once he gets married to Matilda.]]
93* TheCuckoolanderWasRight: He may not know what the definition of "history" is, but he was right about the Horseman being real. [[spoiler: He also correctly remembered that the Sleepy Hollow schoolhouse wasn't built until 1933]].
94* DidntThinkThisThrough: In his effort to sabotage Ichabod's chances with Kat, he didn't think about how this would affect his ''own'' relationship with Ichabod.
95* FratBro: Big into drinking and hanging with his boys, and says things like "Righteous, brah" and "roipe".
96* FreudianSlip: Brom misses his father so much, he sees him everywhere:
97** When Matilda resurrects "Henri", a man around the same age as his father, Brom calls him, "Dad?!" (Despite knowing his father is away).
98** When Ichabod says Brom did good, Brom calls him "Dad", implying WellDoneSonGuy.
99* HeelRealization: After Matilda gives him a ReasonYouSuckSpeech, he realizes his jealous pranks have been cruel to Ichabod.
100--> '''Brom:''' I mean, I see myself as the [[Franchise/BackToTheFuture Marty [=McFly=]]] of my own life, obviously. But... Am I the villain? Did I just Biff my relationship with Ichabod?
101* InUniverseNickname: Affectionately called "Brom Bones" by the town on account of having more bones than the average person. He counts the nickname as part of his full name.
102* JerkJock: Downplayed. He's the gym teacher, and decides to headlock and spook Ichabod out of jealousy, but otherwise seems pretty harmless.
103* {{Malaproper}}: Often misuses words, though he calls it being "wacky with language arts".
104* {{Manchild}}: Ichabod and Diedrich both consider him one, as Diedrich says Ichabod, "[[Needed]] no more proof that Brom had never matured."
105* TheNicknamer: Tends to shorten people's names, like Ichabod to "Icky", Matilda to "Matty" and "Sabrina the Not-So-Teenaged Witch" [[spoiler: and later "wifey"]]. The only exception may be Kat, who already goes by a nickname.
106* OverlyLongName: When including his nickname, Christa thinks he has one of these.
107* ReformedBully: Brom used to be a more typical toxically-masculine bully back in high school, but has tried to be better since becoming a teacher. He feels bad when Matilda calls him out on regressing back to his bullying behavior due to his jealousy of Ichabod.
108* TheStoryteller: Calls himself the local historian. Is the one to tell Ichabod about the Horseman, and tells everyone Lucretia's inn is haunted (much to her frustration).
109[[/folder]]
110[[folder: Matilda Bishop]]
111!! Matilda Bishop
112[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/matilda_bishop_1.jpg]]
113 [[caption-width-right:300:'Matilda Bishop - the town witch, it’s true / She’ll insult and bully and cast a spell upon you'']]
114
115!!!'''Portrayed by:''' Sinead Persaud
116-> ''“Fake book. Good for storing the still-beating hearts of your enemies. Or your inhaler.”''
117
118A witch and a cashier at Colonial Drugs 'N' Stuff. Kat's best friend.
119----
120* BrokenBird: Implied that much of her initial coldness and cynicism is a result of being an outcast, as a witch, [[spoiler: and her guilt over what happened to Kat and Rip Van Winkle the year before.]]
121* CanonForeigner: Of the core four main characters, she's the only one not from "The Legend of Sleepy Hollow".
122* ColorMotif: Wears mostly black throughout the series.
123* CuteWitch: While she's darker and more snarky than this trope usually implies, Matilda is still on the young side for a witch and dresses in cute clothes.
124* DeadpanSnarker: So very much.
125--> "The injustices perpetrated by white cisgender men are what shock me. A headless war veteran in limbo? Not so much."
126* EmbarrassingOldPhoto: Her yearbook photo has her sitting backwards in a chair. She defends that she was told to do that.
127* FantasticallyIndifferent: Since she's a witch, she's completely unfazed by the existence of the Headless Horseman, unlike Ichabod.
128* GoalInLife: Wants to save enough money to open up her own occult shop and help people. [[spoiler: She manages to do this in the finale, alongside Brom.]]
129* GothGirlsKnowMagic: Dresses mostly in black and practices witchcraft.
130* HateAtFirstSight: The minute she sees Ichabod, she proclaims she hates him. However, she seems to soften to him over time.
131* JerkWithAHeartOfGold: While she initially puts down Ichabod and Brom a lot, she and Kat are particularly close. She grows to be more friendly and proves to be a loyal friend.
132* {{Necromancer}}: Matilda is able to temporarily resurrect the dead when she places their skull on the body of the Headless Horseman and casts a spell, but only for a day. [[spoiler: She also brought Kat back by tethering her to Rip Van Winkle's life force using sleeping ivy, but that spell only lasts a year.]]
133* ScrewThisImOuttaHere: Tends to do this soon after reanimating a skull, generally because the skull's personality is too much for her to deal with, leaving Ichabod to flounder alone.
134* SignificantWardrobeShift: She wears mostly black throughout the series. However, she wears a white blouse [[spoiler: after marrying Brom]] and [[spoiler: wears brighter colors in the FlashForward at the end of the series, since she's opened her boutique, leaned into her marriage with Brom, and is no longer haunted by her guilt over Kat and Rip.]]
135* SugarAndIcePersonality: Is mostly cold to Ichabod and even Brom, but she's close friends with Kat for a reason. She's also willing to help Ichabod and the Horseman out despite professing to not like the former and gives Brom a ReasonYouSuckSpeech for regressing to his former bullying behaviors around Ichabod.
136* SuperpowerfulGenetics: Matilda's ancestors were also persecuted for innate magical abilities, suggesting her powers are InTheBlood.
137
138[[/folder]]
139[[folder: Diedrich Knickerbocker]]
140!! Diedrich Knickerbocker
141[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31243_pm_9.png]]
142 [[caption-width-right:300:''Diedrich’s a bard and he’s kind of a jerk / He’ll cut you to shreds with merely a smirk.'']]
143
144!!!'''Portrayed by:''' [[WebVideo/{{PAINT}} Jon Cozart]]
145-> '' '''Ichabod:''' Well? Aren't you going to sing about this? ''
146->'' '''Diedrich:''' Huh? Oh, no. Bard Union says I have to take a four hour break every 30 minutes.''
147
148The narrator and local busker who follows Ichabod around.
149----
150* AllKnowingSingingNarrator: ZigZaggedTrope. While he often seems to know things will happen before they happen, in one scene when Diedrich says Ichabod will be visited by someone, he doesn't actually know who it is. [[spoiler: Yet, he also knows the secret of Kat's death and resurrection, which happened a year prior to the events of the series.]]
151* TheBard: While he's based in Sleepy Hollow, he travels around town to narrate whatever Ichabod is doing -- in song!
152* GreekChorus: Expresses his own opinions on certain proceedings, such as that Ichabod is "not that appealing".
153* InteractiveNarrator: Ichabod is aware of Diedrich's narration, and Diedrich even helps him straighten his tie at one point. [[spoiler: Even more so in the finale, when he helps untie Ichabod and Brom.]]
154* NarratingThePresent: Some of the things Diedrich narrates haven't quite happened yet or are about to happen:
155-->'''Diedrich''': ''(singing)'' ''But before he could start to sob and cry\
156A welcome visitor would soon stop by...''
157--> '''Ichabod''': ''(happily)'' Really? Who?
158--> '''Diedrich''': What? Oh, I don't know.
159[[/folder]]
160[[folder: Verla Wolfson]]
161!! Verla Wolfson
162[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31254_pm_9.png]]
163 [[caption-width-right:300:''When she enters a room, it becomes very cold / Is Verla a haunted doll or 500 years old?'']]
164
165!!!'''Portrayed by:''' Creator/GinnyDi
166-> ''“I told you, she was a doll that came to life.”''
167
168A creepy girl of unknown origins who works at Colonial Drugs 'N' Stuff.
169----
170* CreepyMonotone: Slips into this at times.
171--> '''Verla:''' ''(to Ichabod)'' I will stab you.
172* CreepyShadowedUnderEyes: Between that and her thick bangs, it's hard to see her eyes.
173* EeriePaleSkinnedBrunette: Has long dark hair and pale skin, tends to say disturbing things. May or may not be human.
174* ExtremeOmnivore: Is seen eating glass at one point.
175* GhostlyGlide: Has one in her first appearance.
176* LimitedWardrobe: Wears the same white dress in all appearances.
177* MissingReflection: She doesn't appear in photographs.
178* MultipleChoicePast: Matilda introduces Verla as having [[Film/TheRing crawled out of her TV]], but later theorizes she came from the shut-down girls' orphanage, and even later says she was a doll that came to life. Verla herself mentions being part of a murder trial once and having killed someone via the plague, but due to RefugeInAudacity it's hard to tell what's true and what isn't with her.
179* NightmareFetishist: Her boyfriend is a skull she's named Henri, and she is fascinated by horrific and violent things.
180* StealthHiBye: Tends to pop up very suddenly, startling everyone but Matilda.
181* StringyHairedGhostGirl: While it's unclear exactly what she is, her look is based on one of these.
182[[/folder]]
183[[folder: Baltus Van Tassel]]
184!! Baltus Van Tassel
185[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31304_pm_6.png]]
186 [[caption-width-right:300:''Baltus, the mayor, is everyone’s pal / Wherever he goes, he boosts the morale'']]
187
188!!!'''Portrayed by:''' John Rubinstein
189
190
191The mayor and Kat's father.
192----
193* AdaptationalJobChange: In the original story he was a wealthy farmer, while here he is the mayor.
194* CorruptPolitician: [[spoiler: Planned to poison his political rival Rip Van Winkle, and ended up killing his daughter instead. When Matilda gives him the opportunity the bring her back at the cost of another life, Baltus offers up Rip as sacrifice. He then kills Anne Tarry, pays off Dr. Crayon, and later threatens to kill Judy Gardenier to cover up his crimes.]]
195* LiesToChildren: [[spoiler: Told Kat her mother had drowned when she was 10. 16 years later, she found out this wasn't the truth.]]
196* MayorPain: While he seems like a decent mayor overall, [[spoiler: he poisoned his last assistant for getting too close to the truth about Kat, paid off Dr. Crayon to keep his knowledge of this hush-hush, and imprisoned Ichabod, Matilda, and Brom for also getting too close to the truth.]]
197* RemovingTheRival: [[spoiler: The reason that Kat and Anne died and Rip went missing -- his attempt to get rid of his political rival first went horribly wrong (when Kat died instead), then horribly right (when he was able to use Rip as the sacrifice to bring Kat back), then wrong again (when Kat still dies a year later and Baltus is caught for his crimes, leading Rip to run unopposed).]]
198[[/folder]]
199[[folder: Judy Gardenier]]
200!! Judy Gardenier
201[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31312_pm_1.png]]
202 [[caption-width-right:300:''Judy Gardenier is the mayor’s assistant, / She’s peppy and eager and very persistent.'']]
203
204!!!'''Portrayed by:''' Krystina Arielle
205-> ''“Oh, I'm sorry, but Mrs. Van Ripper had an allergic reaction to the pumpkin spice. I sprayed it everywhere! It's the theme of the party!”''
206
207
208The mayor's assistant.
209----
210* BeleagueredAssistant: Subverted. She is positively perky no matter what she's doing.
211* GenkiGirl: Friendly, sweet, and energetic, she arranged the mayor's party and guest list, making sure Ichabod was introduced to everyone in town. She also delivered Matilda's requested files on beheadings from the town archive to her personally, without batting an eye about the subject matter.
212--> '''Judy:''' ''(sings out as she enters)'' Candygram for Matilda!! Except instead of candy, it's all the local beheading reports since the town was settled.
213* GirlyGirl: Is always seen in cute dresses and makeup, and made the mayor's party pumpkin spice-themed.
214* {{Joisey}}: Has a strong New Yorker/Jersey accent.
215[[/folder]]
216[[folder: Brom's Babes (Tripp, Cal, & Blair)]]
217!! Brom's Babes
218
219[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31320_pm.png]]
220 [[caption-width-right:300: ''Blair, Cal, and Tripp may look mean, dumb, and snarky / But they’re doing their best to smash the patriarchy.'' (From L to R: Blair, Tripp, and Cal) ]]
221!!!'''Portrayed by:''' Creator/JoeyRichter (Tripp), [[Creator/TinCanBrothers Corey Lubowich (Cal) & Brian Rosenthal (Blair)]]
222-> ''“Assemble the babes!”''
223
224
225Brom's posse. Along with supporting Brom, participating in trivia nights, and doing shots, they also host the ''Unsolved Babesteries'' companion series.
226----
227* AscendedExtra: Brom's gang is mentioned only in passing in the original short story. Here, they are significant supporting characters who have names and participate in several important plot events.
228* TheAtoner: Played for laughs. In ''Unsolved Babesteries'', they attempt to do this with their old friend, Spike, after they rejected him for becoming emo in high school, but their attempts come across as shallow rather than genuine.
229* AttentionDeficitOohShiny: They tend to get distracted easily. For example, when they were on the brink of an emotional breakthrough regarding Spike, they got distracted by the idea of tuna fish sandwiches. Eugene calls them out on this in "Anne Tarry" and helps them stay on script.
230* BrainlessBeauty: Failed to remember what catchphrase they agreed on because they didn't write it down.
231* BunnyEarsLawyer: Tripp majored in archaeology, is a bird expert, and was first in his class at Cornell before the NoodleIncident (see TraumaButton below).
232* CoordinatedClothes: Along with Brom, they all tend to wear preppy, light-colored clothes.
233* CrouchingMoronHiddenBadass: In spite of their stupidity, they manage to [[spoiler: pull off the heist, provide distractions so the group can get out of jail and into Dr. Crayon's house, orchestrate Baltus Van Tassel's confession in earshot of Officer Meinhof, and solve the mystery of what happened to Kat's mom.]]
234* FratBro: They are introduced doing shots at the mayor's party.
235* HeroOfAnotherStory: Have their own companion series, ''Unsolved Babesteries'', which aired alongside ''Headless''.
236* IgnorantOfTheirOwnIgnorance: ZigZagged. They show some awareness of their own stupidity when it comes to investigating, averting the trope, but any permanent epiphanies tend to get undercut by AttentionDeficitOohShiny, resulting in IgnoredEpiphany, playing the trope straight.
237--> '''Blair:''' It seems that whenever our desire to improve ourselves meets with our inherent obtusity, the latter comes out on top. Huh.
238* KaleidoscopeHair: Cal's hair switches between black and blond between ''Headless'' and ''Unsolved Babesteries''. This is explained by Cal hiding his natural blond hair with a day wig in public. See RealLifeWritesTheHairstyle on the Trivia page.
239* MeaningfulName: In a meta sense, the initials of the Babes, TCB, also stands for Creator/TinCanBrothers, the actors' production company.
240* PlayingATree: Brom's Babes are listed as "The Set" in the ''A Brief History of Sleepy Hollow'', though they actually play the set as well as all the minor roles since the Trousers fired all of their child actors.
241* PowerTrio: Within their own show, they are the central trio.
242* PreppyName: "Tripp", "Cal", and "Blair".
243* PretentiousLatinMotto: Their crest says "Live, Laugh, Love" in Latin.
244* PrimaDonnaDirector: Cal tries his hand at this in "Devlyn Versace", under Eugene's tutelage.
245* RealMenWearPink: So much so that pink is on their logo.
246* SpiesInAVan: Serve as this twice -- once to feed lines to Anne Tarry [[spoiler: and once to make sure Meinhof got Baltus's murder confession]].
247* ThoseTwoGuys: Those three guys, in this case. In the main series, they mostly hang around and support Brom.
248* TraumaButton: Played for laughs. Mentioning sharks around Tripp causes him to flash back to [[NoodleIncident a past encounter with a shark]].
249--> '''Tripp:''' He had teeth behind his teeth! He had teeth behind his teeth!!
250* WeNeedADistraction: Serve as this twice in "The Clues in the Clink".
251[[/folder]]
252[[folder: Douffe Martling]]
253!! Douffe Martling
254[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31331_pm_9.png]]
255 [[caption-width-right:300:''Ichabod struggles to not go astray / Lest he face the wrath of the uptight Douffe.'']]
256
257!!!'''Portrayed by:''' Joanna Sotamura
258-> ''“When you’re a wealthy landlord with incredible hair, you can make your own rules.”''
259
260Ichabod's demanding landlord. In a double catfish marriage with Dr. Geoffrey Crayon.
261----
262* AdaptationPersonalityChange: Douffe in the original text is mentioned as someone who told tall tales about their war exploits, while modern Douffe is a cold RichBitch.
263* TheAlcoholic: Is seen with a cartoonishly large martini glass at the mayor's party.
264* AssholeVictim: [[spoiler: Douffe gets stabbed in Episode 3, having been a generally unpleasant RichBitch who constantly raised Ichabod's rent for unfair reasons and tried to take something that wasn't hers as collateral. Helps that she's OnlyMostlyDead.]]
265* TheBusCameBack: [[spoiler: Gets stabbed at the end of Episode 3 and isn't seen again until the end of Episode 7, when she wakes up from her stabbing-induced coma]].
266* CompositeCharacter: With Hans van Ripper, Ichabod's apathetic landlord in the original short story. BonusMaterial indicates that a character named [[GenderFlip Hanna van Ripper]] was originally planned for ''Headless'' as Ichabod's landlord, with Douffe serving as Ichabod's boss, but the two were combined in the final version.
267* TheCracker: She "hacks" into Ichabod's Instagram in the first episode [[spoiler: and serves as the hacker during the heist in Episode 8]].
268* CrankyLandlord: She never smiles and is never kind to Ichabod.[[spoiler: She's even crankier when she wakes up from her coma, which she blames Ichabod for]].
269* GenderFlip: Douffe Martling in "The Legend of Sleepy Hollow" was a "large blue-bearded Dutchman" and Revolutionary War veteran, while here she is a woman.
270* RichBitch: Mercilessly raises Ichabod's rent $1,000 more than what they initially agreed on based on slights.
271* ScrewTheRulesIHaveMoney: See her character quote above.
272[[/folder]]
273[[folder: Lucretia Lazenby (SPOILERS)]]
274!! Lucretia Lazenby[[spoiler:/Oksana Bolshekov]]
275[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_31342_pm_5.png]]
276 [[caption-width-right:300:''Lucretia Lazenby makes her way about town / ‘Cause running a haunted inn would make anyone frown'']]
277 [[caption-width-right:300:[[labelnote: Click here to see her in Episode 8]]https://static.tvtropes.org/pmwiki/pub/images/screen_shot_2023_08_06_at_40005_pm_2.png [[/labelnote]]]]
278
279
280
281!!!'''Portrayed by:''' Sarah Grace Hart
282-> ''"I care about booking rooms. But, no. The ground is too unstable for my expansion plan. And the attic is too infested with historic mold for my de-molding project. Please excuse me. God bless America."''
283
284
285The prickly new owner of the Storms Inn, a supposedly haunted inn and the oldest building in Sleepy Hollow. [[spoiler: Actually a former international super spy in witness protection.]]
286----
287* AlliterativeName: '''L'''ucretia '''L'''azenby.
288* APupilOfMineUntilHeTurnedToEvil: Downplayed. [[spoiler: As Oksana, she was Paulie Tahoe's greatest student and worst nightmare, since she often pulled jobs against him. However, she was not necessarily "evil", just an antagonist to Tahoe.]]
289* CrankyLandlord: She's unable to do much with the Storms' Inn due to outside conditions, so she's struggling to make any profit.
290* {{Expy}}: [[spoiler: Of Sidney Bristow from ''Series/{{Alias}}'', as well as red-headed Eastern European female spies like ComicBook/BlackWidow and Tatiana Slozhno from ''Theatre/SpiesAreForever'']].
291* LadyInAPowerSuit: Downplayed, but wears suit jackets in most of her appearances.
292* SuspiciouslySpecificDenial: "...and my hair has always been this color and length."
293* TranquilFury: Threatens Brom in a low voice if he or any of his friends are seen around the inn during the wedding, she will carve his eyeballs out.
294-->'''Lucretia:''' There are 200 ways I could do it using only what's on my person at this second.
295* WigDressAccent: [[spoiler: Her hair is naturally red, but she wears a brunette wig as Lucretia. Since she's originally Lithuanian she is assumed to have changed her natural accent as well.]]
296[[/folder]]
297!Sleepy Hollow Residents
298In order of first appearance.
299[[folder: Rip Van Winkle]]
300!! Rip Van Winkle
301!!!'''Portrayed by:''' James Tolbert
302
303
304The previous middle school science teacher who mysteriously went missing a year prior. Briefly appears in the ActionPrologue.
305----
306* CoolTeacher: Discussed. Christa Pierson remembers him for using examples in class.
307* DistressedDude: [[spoiler: Was kept under a sleeping spell for a year while Kat fed on his life force.]]
308* FaceOnAMilkCarton: His missing poster is still displayed in town, even a year after his disappearance.
309%%* RipVanTinkle: [[spoiler: He's starving when he wakes up.]]
310* RipVanWinkle: Based on the TropeNamer. [[spoiler: Is kept under a sleep spell for a year.]]
311* UnwittingInstigatorOfDoom: [[spoiler: Running against Baltus, not drinking the poisoned wine meant for him, and letting Kat take his glass at the Autumn Gala led to Kat and Anne Tarry's deaths]].
312[[/folder]]
313[[folder: Eugene & Ramona Trousers]]
314!! Eugene & Ramona Trousers
315!!!'''Portrayed by:''' Curt Mega & Kim Whalen
316-> ''" Are you filming in PORTRAIT MODE?!"''
317
318
319Owners of the Eugene and Ramona Trousers School of Acting for Children.
320----
321* AttentionWhore: In ''Unsolved Babesteries'', they immediately pull the attention away from the Babes while on camera.
322* CoordinatedClothes: Tend to wear similar colors, such as tans and dark greens.
323* CreatorCouple: InUniverse, Eugene and Ramona are both actors, playwrights, and acting teachers. Doubles with Curt Mega and Kim Whalen being this in real life.
324* DramaQueen: Ramona when playing the piano.
325* HeroOfAnotherStory: Feature in the ''Unsolved Babesteries'' companion series.
326* HistoryWithCelebrity: Parodied.
327** Supposedly, Eugene was once in a Creator/RobertAltman film... before he got recast for SpikingTheCamera.
328** "Creator/AaronSorkin once told me -- in a podcast I was listening to --"
329* MediumAwareness: "I sense the focus of the scene is shifting away from us."
330* MethodActing: Ramona insists that she must immerse herself in the world of anything she is doing, even a commercial.
331* TheMovieBuff: As actors and acting teachers, they are knowledgeable about films and the proper way to frame shots.
332[[/folder]]
333[[folder: Dr. Geoffrey Crayon]]
334!! Dr. Geoffrey Crayon
335!!!'''Portrayed by:''' Parvesh Cheena
336-> '' "You know it's always 'Look at this, Geoffrey. Diagnose me, Geoffrey.' It's never, 'How are you, Geoffrey? How's ''your'' rash, Geoffrey?"''
337
338
339Sleepy Hollow's physician-in-chief in a double catfish marriage with Douffe.
340----
341* TheEeyore: Generally a negative person -- The only time he's seen as happy is when he divorces his wife. Described in one script draft as "Eeyore's human form".
342* DrJerk: Has traces of this, considering he may have catfished his current wife and how frustrated he gets with Ichabod's question. [[spoiler: Is also being paid off by Baltus to keep the truth about Kat a secret.]]
343* HenpeckedHusband: Compared to Douffe, he has a more timid personality. Downplayed, since he was willing to change the locks the minute the divorce papers went through... ''while she was in a coma''.
344* UnwittingInstigatorOfDoom: [[spoiler: If he hadn't demanded more shush money from Baltus at just the wrong time, Anne Tarry never would have been murdered.]]
345[[/folder]]
346[[folder: Trevor Trinkets]]
347!! Trevor Trinkets
348!!!'''Portrayed by:''' Christopher Higgins
349-> '' "I'm 15. Well, I'll be 15 next month. It's scary." (sips juice box)''
350
351
352The (supposedly) 15-year-old star student at the Eugene and Ramona Trousers School of Acting for Children.
353----
354* AlliterativeName: '''Tr'''evor '''Tr'''inkets.
355* BadBadActing: His performance in ''A Brief History of Sleepy Hollow'' would work for a child actor, but not for someone who is supposedly 15 and looks 30.
356* DeliberatelyCuteChild: The "child" part is debatable, but he plays up his cuteness in performance.
357* HistoryWithCelebrity: Parodied. According to him, Millie Bobbie Brown once looked at him during an audition. Apparently it wasn't even really Millie - it was just a picture of her on another boy's ''Series/StrangerThings'' t-shirt.
358* LargeHam: When onstage.
359--> '''Trevor''': ''(in character)'' STAY AWAY FROM RAVEN ROCK!
360* TroublingUnchildlikeBehavior: Played for laughs when Trevor manages to open a wine bottle for Ichabod, despite supposedly not being of legal drinking age.
361* VagueAge: Says he's 14 going on 15 years old in one episode, but says he was 8 just five years ago in another episode, which would make him 13. This, plus him looking 30, makes it hard to place his actual age.
362* YoungerThanTheyLook: Discussed. Ichabod looks mildly horrified when Trevor says he's only 15, and says he looks 30 throughout the ''History of Sleepy Hollow'' performance (Lampshading the fact that [[DawsonCasting his actor is a contemporary of the rest of the adult cast]]).
363[[/folder]]
364[[folder: Christa Pierson]]
365!! Christa Pierson
366!!!'''Portrayed by:''' Audrey Grace Marshall
367-> ''"Teachers have first names?"''
368
369
370A student at Sleepy Hollow Middle School.
371----
372* BrutalHonesty: Tells her gym teacher he has "too much name".
373* ComicallyMissingThePoint: First, she mentions how her mother's "private pottery teacher" stopped coming around the house (justified because ChildrenAreInnocent). Then, after Ichabod realizes that her previous teacher "Mr. Van Winkle" was Rip Van Winkle from the missing posters, she's more surprised that teachers have first names.
374[[/folder]]
375[[folder: Officer Meinhof]]
376!! Officer Baader Rhonda Meinhof
377!!!'''Portrayed by:''' Corey Dorris
378-> '' "Once you're on my radar, you start seeing me everywhere." ''
379
380
381Local police sheriff.
382----
383* ConsummateProfessional: ZigZagged. When he [[spoiler: arrests Baltus]], he says, "You have the right to remain totally owned!". However, he insists Brom's Babes made him say that and that he is too professional to say it himself (and yet seems a little too smug for that to be true).
384* GenderBlenderName: Downplayed -- his middle name is "Rhonda".
385* {{Jerkass}}: He plays the InstantWebHit video where Ichabod got slimed while Ichabod is right there in the cell nearby, ''on Ichabod's phone'', rubs in that Ichabod has nobody to check up on him, and then agrees to sign up for a bundled cable package under Ichabod's name.
386* MeaningfulName: His 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. Doubles as GeniusBonus.
387* MeddlesomePatrolman: Doesn't allow Ichabod to explain himself when he catches him in the graveyard, slaps him with a court order, and almost takes him down to the station then and there just for speaking out of turn.
388* NotSoAboveItAll: Zigzagged. See the ConsummateProfessional example above.
389* ReasonableAuthorityFigure: Despite his jerkass behavior (above) [[spoiler: he turns out not to be in cahoots with the mayor when he arrests Baltus for Anne Tarry's murder after hearing his accidental confession.]]
390[[/folder]]
391[[folder: Judge Pringle]]
392!! Judge Pringle
393!!!'''Portrayed by:''' Julia Cho
394-> '' "Ichabod Crane. You are sentenced to 50 hours of community service. [...] And Devlyn Versace. My socials need a glow-up! Can you help me?" ''
395
396
397The Sleepy Hollow court judge.
398----
399* InstantWebHit: After Devlyn set up her Youtube channel, she got 50,000 subscribers overnight on her first video, "Real Judge Reacts: ''[[Film/MyCousinVinny My Cousin Vinny]]'' ".
400* MoodSwinger: Goes from serious judge to trend-following valley girl on a dime.
401* NoFullNameGiven: Unlike most of the characters in the show, Judge Pringle's first name is never revealed.
402* NotSoStoic: Though she appears as a stern IronLady judge (and acts as such towards Ichabod), she is not above wanting the latest iPhone or going along with Devlyn's antics.
403[[/folder]]
404[[folder: Jonathan Oldstyle]]
405!!Jonathan Oldstyle
406!!!'''Portrayed by:''' Tom Lenk
407
408
409A new bard in town.
410----
411* TheBard: In his job description, thought he is more ska and less folk than Diedrich.
412* LastEpisodeNewCharacter: Appears at the top of the final episode with no explanation.
413* RemovingTheRival: [[spoiler: Kills Diedrich before attempting to replace him as the Sleepy Hollow bard.]]
414* TheRival: Implied that he and Diedrich have a history of competition.
415* {{Ska}}: How he defines his bardic style.
416* WeHardlyKnewYe: Appears in three scenes in the final episode [[spoiler: before getting stabbed.]]
417* WeNeedADistraction: Lures [[spoiler: Kat and Matilda]] away from the heroes [[spoiler: so Diedrich can free Brom and Ichabod]].
418[[/folder]]
419!Horseman's Heads
420In order of first appearance
421[[folder: General]]
422* BackFromTheDead: Matilda's spell combines the life force of the Horseman's body with the spirit from whatever skull they they choose to place on his neck. The Horseman then takes on the identity of the skull, briefly bringing that person back to life (complete with anything they had on them, from Max's Revolutionary War costume to Devlyn's phone).
423* DeadToBeginWith: All the Horseman's Heads died prior to the series, ranging from centuries ago to as soon as three weeks before. [[spoiler: Subverted with Diedrich, whose presence as a Head serves as a GhostlyDeathReveal in the finale.]]
424* EstablishingCharacterMoment: Since each head only gets an episode, they tend to make a big first impression.
425* {{Hammerspace}}: Devlyn managed to summon a blowhorn, DJ equipment, and slime from seemingly nowhere, and Paulie Tahoe is constantly manifesting martinis in his appearances.
426* MagicPants: In spite of the otherwise changing outfits, each of the heads wears the Horseman's pin somewhere on their person. Doubles as MorphicResonance.
427* MorphicResonance: Downplayed -- the pin (under MagicPants) is the only feature that ties the heads together. Justified, since each head was originally their own person.
428* OneShotCharacter: Since the heads only last for a day with mugwort, each character lasts for about an episode (sometimes less) before returning to the afterlife. [[spoiler: Averted with Paulie Tahoe, who appeared across three episodes, though justified since they took place over a single day. Subverted with Diedrich, who was a main character before his death.]]
429* RidiculouslyAliveUndead: All of the resurrected are exactly as they were in life, with Captain Gravy able to drink alcohol to the point of passing out drunk, and Max Lee and Devlyn both eating a ton of snacks. Max also seems to come back still stoned and able to smoke, while Devlyn says she may still have Adderall in her system from before her death.
430* UndeathAlwaysEnds: The heads only last a day, after which the person goes back to being dead. Their undeath can also end sooner if the head is melted off or if they are killed again.
431[[/folder]]
432[[folder: Head #1 -- [[spoiler: "Henri"]]]]
433!! "Henri"
434!!!'''Portrayed by:''' Jason Huber
435
436
437A 55-year-old male whose skull was named "Henri" by Verla. The first identity the Horseman takes on.
438----
439* DramaticIrony: "Oh, thank God. I thought I was dead."
440* WeHardlyKnewYe: [[spoiler: Only got to say one line before the spell reverted.]]
441[[/folder]]
442[[folder: Head #2 -- [[spoiler: Captain "Gravy" Davy Crowbones]] ]]
443!! Captain "Gravy" Davy Crowbones
444!!!'''Portrayed by:''' Creator/MatthewMercer
445-> ''"Avast, ye shoddy bilge rats! 'Tis I, Cap'n "Gravy" Davy Crowbones, scourge of the Hudson Harbor!!" ''
446
447
448A 17th-Century pirate and the second identity the Horseman takes on.
449
450----
451* AlwaysIntroducesThemselves: Gives a long introduction of himself to every character he meets.
452* BewareTheSillyOnes: Gravy might be an over-the-top drunken pirate with a silly name, but he's still a pirate. [[spoiler: He [[GuttedLikeAFish does not react well]] to Douffe trying to take his [[LostLenore Lost Lenore's]] necklace.]]
453* BloodKnight: Tends to go for his sword in a conflict.
454* TheCasanova: Flirts with Verla and Kat, while holding a torch for his LostLenore Juniper.
455* ConnectedAllAlong: [[spoiler: Gravy's lover, Juniper, was one of the witches who cursed Henrietta, creating the Headless Horseman. As such, Gravy's PirateBooty holds the literal key to the mystery of who the Horseman is.]]
456* DressedToPlunder: He wears the classic coat and three-corner hat of a pirate.
457* GhostPirate: Played with -- He died centuries ago and has been resurrected briefly through Matilda's magic, but is more flesh-and-blood than a ghost.
458* LargeHam: As a caricature of the classic cinematic swashbuckling pirate, he leans hard into this.
459* LargeHamTitle: Changes it, depending on who he's talking to. The list includes:
460** "Scourge of the Hudson Harbor"
461** "[[AnimalLover Friend to Animals]]"
462** "Architect of the San Juan Swizzle"
463** "Lover of Juniper Lebouf, Lady of a Thousand Sapphires"
464** "Tyrant of Eastern Copenhagen"
465* NightmareFetishist: Flirts with Verla, despite her creepy vibes.
466* OverlyLongName: Introduces himself to Kat as "Gravy Aloycious 'Two Sleeve' Davy Crowbones"
467* PirateBooty: Recovers a small chest of his treasures and possessions, including his sea log and his lover's necklace. Downplayed, since it's a small chest and mostly contains items of personal value.
468* RhymingNames: "Gravy Davy".
469* TalkLikeAPirate: He talks like a stereotypical movie pirate, especially when drunk.
470--> "What's the mayhaps and grumblins over yonder, ye skronky bonkers?"
471* TragicKeepsake: One of his treasures is a necklace that belonged to his love [[LostLenore Juniper]], whom he met and lost in Sleepy Hollow.
472
473[[/folder]]
474[[folder: Head #3 -- [[spoiler: Max Lee]] ]]
475!! Max Lee
476!!!'''Portrayed by:''' Jimmy Wong
477-> '' "Oh, snap! I'm alive! Yo, this is tight!" ''
478
479
480A Revolutionary War reenactor whose head Matilda mistook for a real Revolutionary solider's. He died after getting too close to the cannons during the biannual reenactment of the Battle of White Plains in 2015.
481----
482* BigEater: Is constantly snacking throughout the play. This may be partly due to his pot smoking giving him the munchies.
483* GeniusDitz: While he's a goof, he points out the historical inaccuracies in the Trousers' ''A Brief History of Sleepy Hollow'' play. Lampshaded.
484--> '''Max:''' Man, I know so much stuff! I really wasted my potential. ''(takes ham out of his pocket)'' [[MoodWhiplash Ham?]]
485* TheHedonist: Is happy to be alive again and mostly focuses on smoking and snacking on whatever he can find. In life, he delivered and smoked marijuana when he wasn't being a reenactor.
486* RedHerring: Matilda picks his head in hopes they can get some information about Headless from someone who fought in the same war... except Max is in fact not a real solider, just a reenactor. [[spoiler: Subverted, since he does point out that there was no Revolutionary War battle in Sleepy Hollow, providing a clue that Headless might not be a Hessian mercenary after all]].
487* TheStoner: He knows his weed, as he both smokes and delivers the stuff.
488* TooDumbToLive: Tried to smoke ivy, which is ''poisonous to humans''. He also freely discusses selling and taking marijuana despite the fact that, at the time of his death in 2015, it was illegal to sell marijuana for purposes other than medicinal ones in New York State.
489* TraumaButton: Even after his death, his encounter in the woods with the Woman in White still haunts him.
490* WarReenactors: Max died reenacting the Battle of White Plains, and was so dedicated he bribed the funeral home to bury him under a tombstone that listed his death year as 1776.
491[[/folder]]
492[[folder: Head #4 -- [[spoiler: Devlyn Versace]] ]]
493!! Devlyn Versace
494!!!'''Portrayed by:''' Lee Newton
495-> '' "Heyyyy, what's up fam? It's your girl, Devlyn Versace, coming atchya! Hopin' all my little Deviled Eggs are ready to get their yolks scrambled, son! GONZO!!!" ''
496
497
498A recently-dead Youtube prankster who Brom got to be Ichabod's counsel instead of the top-notch attorney Ichabod asked for.
499----
500* BadInfluencer: She turns Ichabod's court date into a chaotic debacle, including sliming him and pulling down his pants. Prior to that, she sponsored countless shady apps, gaslit her sister, brought an ostrich into the Oval Office, snuck alligators into a hospital, and started a social media university.
501* BigBrotherBully: Implied. Devlyn rose to fame after telling her younger sister that aliens were coming to take her back to the mothership. Many of her videos feature her gaslighting her sister in this way, up to and including telling her she was ''dead.''
502* BigEater: The court room table is covered in snack bags when Ichabod enters court, implying this.
503* {{Catchphrase}}: Has 4200 of them according to her, including "Yoinkies, yoinkies, yoinkies!!!!" and "GONZO!!!"
504* DeadlyPrank:
505** Was bungee jumping off of a turbo blimp for a prank when the cord snapped and she plummeted to her death.
506** Based on implications from a FreezeFrameBonus in her ''Unsolved Babesteries'' episode, she illegally brought live hungry alligators to a ''children's hospital''. The prank apparently got out of hand and the paramedics had trouble handling it, leading to some rather UnfortunateImplications.
507* DontTryThisAtHome: Gives this disclaimer at the end of her video because she is supposedly a professionally-licensed prankster.
508* FormerChildStar: She started going viral at 10 years old.
509* HiddenDepths: Has a degree in Biochemistry from MIT, plus two years of magician's training.
510* MeaningfulName: Her first name sounds like "devil", since she's such a devilish prankster. She uses this in a lot of her branding.
511* ThePrankster: Seems to be her main claim to fame (though she also makes videos about fanny packs).
512* PungeonMaster: She uses her name for a number of punny branding titles, including "Devlyn's Advocate" and "Devlyn's in the Details". She [[FanCommunityNicknames also calls her fans her "Deviled Eggs"]].
513* RichBitch: She grew up the daughter of a hedge fund manager, went to a private school within a private school, and gained a lot of rich friends through her Youtube following.
514* SmokeOut: Successfully uses one in the court room to disappear and reappear behind Judge Pringle.
515--> '''Devlyn:''' Boom! That's what two years at Houdini Summer Camp for Children will getcha. Thanks, Mom! Suck it, U.S. Legal System!
516* SocialMediaBeforeReason: Is constantly streaming throughout Ichabod's trial, and was editing a video in the middle of a bungee jump.
517* TooDumbToLive: Along with editing a video while jumping out of a blimp in the first place, looking at her previous video titles, she once forgot her account password, made a new channel, remembered the password... and ''put that password in the title of a video''. She then posted a video about how upset she was that so many of her viewers stole her password.
518* VillainWithGoodPublicity: Downplayed, but despite her abrasive personality, her fashion line apparently sold to such stars as Michelle Obama, Helen Mirren, and Malala Yousafzai.
519[[/folder]]
520[[folder: Head #5 -- [[spoiler: Anne Tarry]] ]]
521!! "Anne Tarry" (Annefred Paragon Tarrysmith)/ "Mahk"
522!!!'''Portrayed by:''' Creator/LaurenLopez
523
524
525Baltus Van Tassel's previous assistant who died the year before under mysterious circumstances. She wants justice.
526----
527* EarlyBirdCameo: All of the heads up until Anne's appearance had gotten their own DayInTheLimelight episodes, but Anne appears at the end of Episode 5 to deliver a WhamLine.
528* OverlyLongName: If the full name the Babes refer to her as, "Annefred Paragon Tarrysmith", is real, then she counts as this.
529* PaperThinDisguise: Her "Mahk" disguise is simply her in a baseball cap and mustache using a strong Boston accent. Yet somehow it manages to fool her former boss, who worked up close with her for years.
530* {{Southies}}: Her "Mahk" persona is essentially a South Boston Mark Wahlburg {{Expy}}, accent and all.
531* SurprisinglyRealisticOutcome: After multiple heads who have no problems with their resurrection, she's the first head to be confused and scared at waking up from death in a strange place with people she doesn't recognize.
532* SweetPollyOliver: Dresses up as "Mahk" so she can get Baltus to confess to killing her without revealing she's BackFromTheDead.
533* WhatTheHellIsThatAccent: She tries a German and South African accent with the Babes before going undercover and does horribly.
534[[/folder]]
535[[folder: Head #6 -- [[spoiler: Bruce [=McConnell=]]]]]
536!! Bruce [=McConnell=]
537!!!'''Portrayed by:''' Dan Mintz
538-> '' "Do we have any organ donors in the house tonight?" ''
539
540
541A stand-up comedian.
542----
543* IronicAllergy: The stand-up comedian died from a [[ProducePelting severe tomato allergy]].
544* ForgettableCharacter: He was once booked to perform on ''Series/TheTonightShowWithJayLeno'', but didn't get a chance because the staff forgot he was there.
545* TheGimmick: His "Hot Takes with Bruce [=McConnell=]" segment (which consists of very lukewarm "hot takes").
546* SoUnfunnyItsFunny: Bruce delivers his jokes in such a flat monotone voice, his unfunny jokes become funny.
547* WeHardlyKnewYe: Lasts for all of one scene.
548[[/folder]]
549[[folder: Head #7 -- [[spoiler: Paulie Tahoe]]]]
550!! Paulie Tahoe
551!!!'''Portrayed by:''' Ryan W. Garcia
552-> '' "I just have one question: Aces high or low?" ''
553
554
555A legendary thief Matilda recruits to get into Storms Inn.
556----
557* {{Biopic}}: In-universe, Paramount bought the exclusive rights to his life story in 2018, producing it as ''The Paulie Tahoe Story''.
558* TheCasanova: In his lifetime, he had multiple divorces, two secret families, and definitely some kind of thing going on with his pupil, Oksana Bolshekov.
559* TheCharmer: He's a smooth operator and compliments women easily, but is also focused on the task at hand when it comes to heists.
560* TheChessmaster: His role in every heist. He anticipates even the weirdest twists and turns, saying it's "All part of the plan". [[spoiler: The one thing he couldn't plan for was him dying again and reverting to Headless before he could bust Ichabod, Brom, and Matilda out of jail.]]
561%%* TheComicallySerious
562* EarlyBirdCameo: Appears at the end of Episode 7 before having a larger role in Episode 8.
563* GentlemanThief: Has a reputation as a master thief, is introduced with a martini in hand, and reportedly never wears the same suit twice.
564* ShroudedInMyth: The Babes and Brom introduce him as having stolen a slot machine from a casino in broad daylight and being the reason Ben Affleck and Jennifer Lopez broke up ''and'' got back together. He was buried in Sleepy Hollow so his enemies wouldn't defile his grave.
565
566[[/folder]]
567[[folder: Head #8 -- [[spoiler: Diedrich Knickerbocker]] ]]
568!! Diedrich Knickerbocker
569!!!'''Portrayed by:''' Jon Cozart
570
571
572See Diedrich's folder under "Main Characters" for more about his personality. Tropes here will deal with his death and afterlife.
573----
574* FriendlyGhost: He hangs around Sleepy Hollow and becomes Ichabod's pseudo-roommate. As a Head, he also unties Ichabod and Brom.
575* GhostlyDeathReveal: His head being used for Headless reveals he was the body in the morgue and was just killed.
576* KilledOffForReal: While he briefly comes back as a Head, Diedrich is permanently dead once Kat stabs him.
577* KilledOffscreen: Murdered at some point between Episode 7 and Episode 10 by Jonathan Oldstyle. The cast doesn't even know he's dead until his head is placed on Headless's body.
578* MonsterRoommate: Seems to be Ichabod's ghost roommate in the finale.
579* PosthumousNarration: "Ended Up Captured", "It's Been A Few Months", and "One Last Song" all occur after his death, counting as this.
580[[/folder]]
581[[folder: The Horseman's True Identity (SPOILER CHARACTER)]]
582!!Henrietta Hudson
583!!!'''Portrayed by:''' Creator/FeliciaDay
584-> '' "I've been many people over the years. Explorer. Sorcerer. And a headless ghost. I'm Henrietta Hudson. I'm the founder of Sleepy Hollow." ''
585
586
587The true founder of Sleepy Hollow, cursed to become the Headless Horseman when her second-in-command and husband both betrayed her in the 1600s.
588----
589* ActionGirl: Even under the Headless curse, she is nimble with a sword.
590* BeethovenWasAnAlienSpy: The person who settled the Hudson Valley was a witch who became the Headless Horseman.
591* BenevolentMageRuler: Under the witch Henrietta, the Sleepy Hollow settlement thrived.
592* BewareTheNiceOnes: She's deadly with a sword and still likely killed Anneke Storms out of vengeance.
593* BoldExplorer: Defines herself as such, since she captained her own ship and discovered the Hudson River on her way to Asia.
594* TheCaptain: Served as captain of the Liechtgevund, safely getting her ship to the New World.
595* ChekhovsGunman: She is first mentioned in the Trousers' play in "The Star on the Stage" as a minor figure in the town's history. She turns out to be central to the Headless mystery and the town's history.
596* CoolSword: Her sword, Glory, is a plain but beautiful sword.
597* DisappearsIntoLight: Vanishes into subtle swirls of gold energy when Ichabod looks away. Combined with FadingAway.
598* HistoricalGenderFlip: Is one, in a sense, for the explorer who discovered the Hudson River. Downplayed since the real Henry Hudson exists in this universe, he's just not the true founder.
599* TheLeader: She seemingly lead both the Sleepy Hollow colony and her witch coven successfully until TheMutiny.
600* SamusIsAGirl: The Horseman is a "Horse Her".
601* {{Tomboy}}: Dresses in pretty gender-neutral clothes considering the time period she is from.
602* UnPerson: Her role as the true founder was erased from history, with everyone thinking her husband Henry discovered the Hudson River and founded Tarrytown and Sleepy Hollow. Henry's boat had actually drifted to Nova Scotia, and when he made it to Sleepy Hollow he was jealous of Henrietta's success. Anneke's Headless curse was a way to erase her identity, both from herself and from history. Inverted in the finale, as her head is restored and her contributions to history are made known.
603[[/folder]]
604!''Unsolved Babesteries''-Exclusive Characters
605[[folder: Spike]]
606!! Spike
607!!!'''Portrayed by:''' Blake Silver
608-> '' "Also my therapist said speaking to you three might help... heal me? Might help me move on from the turmoil of high school. Might help me stop speaking solely in Music/DeathCabForCutie lyrics." ''
609
610
611The former fourth Brom's Babe who was rejected by the other three in high school when he became {{Emo}}. The Babes use ''Unsolved Babesteries'' as an attempt to make amends.
612----
613* AwLookTheyReallyDoLoveEachOther: Despite his frustration and troubled past with the Babes, he agrees to help them with their videos and reluctantly accepts their affections. [[spoiler: In the finale he is touched by their clip show of him and finally forgives them, asking them to visit him in Connecticut.]]
614* DarkAndTroubledPast: An encounter [[spoiler: with the Woman in White]] in the Sleepy Hollow woods triggered Spike's descent into darkness, so much so that he refuses to talk about it.
615* EeriePaleSkinnedBrunette: Downplayed. While he has naturally pale skin and a gloomy vibe, he's rarely full-on creepy.
616* TheEeyore: Has a gloomy personality and is in therapy, but his sadness comes off as amusing in the context of the series.
617* {{Emo}}: Downplayed. While he traded his faux hawk and black nail polish for a computer science degree and a house in Providence, RI, he still wears {{Guyliner}} and quotes "emo" genre music.
618* EmoTeen: Formerly. This is how he got let go by Brom's Babes in high school.
619* OddNameOut: When alongside the Babes, Spike's name stands out from the preppy Tripp, Cal, and Blair.
620* SayingSoundEffectsOutLoud: He says the word "sigh" to indicate his frustration, which Tripp lampshades.
621* TheSmartGuy: Of the Babes, he's the one who does the research and considers deeper questions.
622* SurroundedByIdiots: A non-villainous example. Regards the Babes as such, too caught up in boat shoes and kegs to have perspective on humanity.
623* TearsOfJoy: Spike is touched by the Babes making a clip show just for him.
624* VampireVannabe: Potentially, if this line is any indication:
625--> '''Spike:''' ''(agitated)'' I am pale, like a vampire. A very hot vampire with several problems.
626* WeUsedToBeFriends: Spike is still scarred from the Babes' rejection back in high school, and struggles to trust them again throughout the mini-series.
627[[/folder]]
628[[folder: Ryan W. Garcia]]
629!!Ryan W. Garcia
630!!!'''Portrayed by:''' Ryan W. Garcia
631
632
633An actor hired to play Paulie Tahoe in the biopic about his life, ''The Paulie Tahoe Story''.
634----
635* AsHimself: The credits list him as such: "Ryan W Garcia as Ryan W Garcia".
636* CelebrityParadox: Actor Ryan Garcia exists in the ''Headless'' and ''Unsolved Babesteries'' universe, despite the fact that the real Ryan plays Paulie Tahoe in ''Headless''. Even more paradoxically, in-universe Ryan Garcia has been hired to play Paulie Tahoe in a biopic about his life. This is lampshaded by Tripp pointing out Ryan's "uncanny resemblance" to the in-universe Paulie Tahoe.
637* MethodActing: Taken to the logical extreme. In order to get into character as criminal mastermind Paulie Tahoe, Ryan actually robbed banks, committed heists, and kidnapped a few president's daughters. The Babes initially think he's joking, but then the police sirens start going off in the distance...
638-->'''Cal:''' ''(jokingly)'' Well then, I bet those sirens in the distance are for you then?
639-->'''Ryan:''' ''(deadpan)'' Oh no, they are. They are for me.

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