History Trivia / HeadlessASleepyHollowStory

** In Episode 2, Ichabod says Matilda would make a good tour guide. Both Ichabod's and Matilda's actors were museum tour guides in high school and college, with Sinead Persaud in particular serving as tour guide for the Salem Witch Dungeon.

** In "Bruce [=McConnell=]", Cal refers to the Babes as his "wolf pack" and they howl together. Later in the episode, Blair wonders if ''Unsolved Babesteries'' should have been a podcast instead. Creator/TinCanBrothers, who play the Babes, produced the ''WebVideo/WaywardGuideForTheUntrainedEye'' web series and [[Podcast/WaywardGuideForTheUntrainedEye companion podcast]], which centered around (were)wolves and featured the members of Shipwrecked Comedy in its cast.

** BonusMaterial exclusive to Kickstarter backers indicates multiple characters were cut from the original draft, including Rip Van Winkle Sr., Hanna van Ripper (would have served as Ichabod's landlord, with Douffe as Ichabod's boss), and Horatio Rook (an additional head).

** 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.
*** To make it even trippier, Ryan, while talking with the Babes, is wearing the t-shirt from a musical the actors playing the Babes produced.

** Mary Kate Wiles plays a secretive, morally-ambiguous antagonist after years of playing earnest, good characters for Shipwrecked. The fact that she is set up as Sean Persaud's love interest (as in previous Shipwrecked works) played on audience expectations.

** Mary Kate Wiles plays a secretive, morally-ambiguous antagonist after years of playing earnest, good characters. The fact that she is set up as Sean Persaud's love interest (as in previous Shipwrecked works) played on audience expectations.

** Sinead Persaud wrote in Ichabod (played by her brother Sean) getting slimed in Episode 5 as a bit of childhood revenge.

** BonusMaterial exclusive to Kickstarter backers indicates multiple characters were cut from the original draft, including Rip Van Winkle Sr. (Rip's dad and another victim of the spell), Hanna van Ripper (would have served as Ichabod's landlord, with Douffe as Ichabod's boss), and Horatio Rook (an additional head).

** The original plan was for the Horseman to go around with a pumpkin as a head when not possessed by another's identity, referencing the iconic depictions of him with a Jack o' Lantern head. However, it was too difficult to keep the pumpkin head balanced, so other workarounds -- such as a parasol -- were utilized, to hilarious effect.

** Creator/MatthewMercer worked with Mary Kate Wiles on ''WebVideo/SchoolOfThrones'' and ''Muzzled the Musical'' back before ''WebVideo/CriticalRole'' was a streaming show. Creator/GinnyDi and Krystina Arielle are also established players in the Critter community, with Ginny's popular character cosplays and Krystina's appearance in one of their one shots.

** Kat's line about putting bad kids in their place may have been a reference to Mary Kate Wiles's role as Miss Vicky in ''Series/TheFairlyOddparentsFairlyOdder'' (Especially considering the appearance of her co-star from that show, Audrey Grace Marshall, in the same episode).

** Creator/MatthewMercer worked with Mary Kate Wiles on ''WebVideo/SchoolOfThrones'' and ''Muzzled the Musical'' back before ''WebVideo/CriticalRole'' was a streaming show. Ginny Di and Krystina Arielle are also established players in the Critter community, with Ginny's popular character cosplays and Krystina's appearance in one of their one shots.

** Sean and Tom Lenk had both worked on the [[https://www.youtube.com/user/30MinuteMusicals ''30-Minute Musicals'' YouTube channel]].

** Tom Lenk and Felicia Day both appear in the finale.

!!Warning! Unmarked spoilers below

** "With [[spoiler:Felicia Day]] as Henrietta Hudson"

** According to [[https://www.tvinsider.com/1058308/headless-a-sleepy-hollow-story-sean-sinead-persaud-matthew-mercer-audrey-grace-marshall-jimmy-wong/ TV Insider]], this was Matthew Mercer's reason for taking time out of his schedule to play [[spoiler: Captain Gravy Davy Crowbones]].

* DirectedByCastMember: Curt Mega directs the ''Unsolved Babesteries'' companion mini-series, which he also plays a featured role in.
* InspirationForTheWork: Sinead Persaud's childhood fanfics of ''Film/SleepyHollow1999''.

** The original plan was for the Horseman to go around with a pumpkin as a head when not possessed by another's identity, referencing the iconic depictions of him with a Jack o' Lantern head. However, it was too difficult to keep the pumpkin head balanced, so other workarounds -- such as a parasol -- were utilized.

* 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.

** In "Paulie Tahoe", Ryan Garcia (the character) wears a ''[[Film/TheMatrix Matrix]] TheMusical'' t-shirt from the Tin Can Brothers' workshop, ''This Could Be On Broadway'', which Ryan (the actor) starred in with Joey Richter and Brian Rosenthal.

* CelebrityParadox: Ryan Garcia the actor exists in the ''Headless'' and ''Unsolved Babesteries'' universe, despite the real-life actor playing Paulie Tahoe, the person Ryan Garcia has been hired to play in-universe. Don't think about it too hard.

** In "Paulie Tahoe", Ryan Garcia (the character) wears a ''Film/TheMatrix TheMusical'' t-shirt from the Tin Can Brothers' workshop, ''This Could Be On Broadway'', which Ryan (the actor) starred in with Joey Richter and Brian Rosenthal.

* In "Paulie Tahoe", Ryan Garcia (the character) wears a ''Film/TheMatrix TheMusical'' t-shirt from the Tin Can Brothers' workshop, ''This Could Be On Broadway'', which Ryan (the actor) starred in with Joey Richter and Brian Rosenthal.

* ActingForTwo: Tom [=DeTrinis=] plays the Horseman, but is hidden under the costume. He also appears out of costume as the Trivia Host in Episode 3.

!!'''Warning! Unmarked spoilers below