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  • Writer's pictureKara Chatham

Headless | Webseries

From the creators of Edgar Allen Poe's Murder Mystery, Invite Only/Gala for Friends Potlock (aka Poe Party), comes another fun literary journey.

Headless: A Sleepy Hollow Story is a modern retelling of The Legend of Sleepy Hollow by Washington Irving. In its ten epsidoes, we get to know Ichabod Crane (Sean Persaud), Matilda Bishop (Sinead Persaud), Brom Bones (Gabe Greenspan), and Kat Van Tassel (Mary Kate Wiles), as they work together to find the head of the Headless Horseman. It is a dark comedy that does not dip too far into the horror nature that can be found in other adaptations of this well known legend.


Sean and Sinead wrote the scripts and adapted this legend beautifully. We have the essence of the original story with a few twists that bring this story into the modern day. They brought in a variety of comedy types, which are only heightened by their killer cast.


This production has quite the stacked cast. All very talented with a plethora of credits to their names. Faces you may recognize if you have seen other projects from Shipwrecked Comedy, Tin Can Bros, StarKid, or YouTube webseries:

  • Sean Persaud (Shipwrecked Comedy member, I Ship It)

  • Sinaed Persaud (Shipwrecked Comedy member)

  • Sarah Grace Hart (Shipwrecked Comedy member)

  • Mary Kate Wiles (Shipwrecked Comedy member,The Lizzie Bennet Diaries, I Shipt It)

  • Gabe Greenspan (American Whoopee, The Case of the Guilded Lily, Wayward Guide)

  • Jon Cozart (PAINT, American Whoopee, Wayward Guide)

  • Joey Richter (StarKid & Tin Can Bros member, I Ship It)

  • Brian Rosenthal (StarKid & Tin Can Bros member)

  • Corey Lubowich (Tin Can Bros member)

  • Lauren Lopez (StarKid, Poe Party, Wayward Guide)

  • Joanna Sotomura (Emma Approved, The Case of the Guilded Lily, Wayward Guide)

  • Curt Mega (Poe Party, Spies are Forever)

  • Kim Whalen (American Whoopee)

  • Christopher Higgins (Poe Party, American Whoopee, The Case of the Guilded Lily)

  • Ryan W. Garcia (Poe Party, American Whoopee, The Case of the Guilded Lily)

  • Jimmy Wong (Poe Party, Video Game High School, MyMusic)

  • Krystina Arielle (Critical Role)

  • James Tolbert (StarKid)

  • Lee Newton (MyMusic)

  • Julia Cho (The Lizzie Bennet Diaries)

  • Matthew Mercer (Critical Role)

  • Felicia Day (Dr. Horrible's Sing-Along Vlog)

Actors you may recognize from non-internet projects:

  • Parvesh Cheena (Crazy Ex-Girlfriend)

  • John Rubinstein (This is Us, Angel)

  • Dan Mintz (Bob's Burgers)

Of the core characters, my favorites are Brom Bones (Gabe Greenspan) and Matilda Bishop (Sinead Persaud). They brought different kinds of comedy to the table and it honestly difficult to not enjoy what they bring to the table. They each stole the show in their own respective ways.


From this point on the review will contain spoilers. If you are not interested in spoilers, then it is advised to stop reading here. Otherwise please enjoy the spoilers below!


The type of character that Kat Van Tassel is is so different from other characters that I have seen Mary Kate Wiles play - and it was so fun! Especially upon watching it again, it was neat noticing the different clues that are dropped along the way that she is the real mastermind behind a lot of what happens in Sleepy Hollow. There is quite a bit that throws suspicion on the Mayor, but it's really the daughter. She flirts with Ichabod to secure her next "life force" as she believes that no one will miss him when the time comes.


Brom Bones goes on such a journey. He has his moments of being a stereotypical jerk, but we really get to see him develope this frienship with Ichabod. It's because of the frienship that we see, that adds to why Brom doesn't seem to bat much of an eye at the fact that Kat is behind the plot.


The Babes. Where to even begin with Brom's Babes? Brian Rosenthal, Joey Richter, and Corey Lubowich are hilarous. The Babes are a bit air-headed, but then again so it Brom. They have their moments when they come across like the enlightened fools of the story. They also had the fun of a companion series - Unsolved Babesteries - where they got to dive in a little more to the lives of the heads that were featured in the series.


I loved the way they utilized the Headless Horseman trying on different heads as a way of finding out the identity of the Headless Horseman. It brought about so many amazing cameos and characters. Favorite character from the mix was Paulie Tahoe - his episode is a heist episode and it is just so much fun to watch. Favorite cameo from the Headless Horseman Heads - Felicia Day! All of the different actors who got to play a version of the Horseman were fantastic, but personally I enjoyed the heist episode the most. While I loved watching Lauren Lopez, I did find the episode she was in to be a bit tough to get through. That is simply because second-hand embarrassment is a very real thing, and I definitely cringed at a couple spots in that episode.


The Mayor (John Rubinstein) from the get go seemed a tad shady to me. But is it something that can be chalked up to stereotypical politician stuff - especially as his main motivation is to keep the role of Mayor of Sleepy Hollow. But he does have a secondary motivation of keeping his daughter alive.


Not gonna lie, I was half expecting Judy, the Mayor's assistant, to be in on what was going on with the Mayor. But it was fun to see her help our heroes acquire everything they needed along the way. She even helped Brom and Matilda get married, which turned into giving them a crucial piece of evidence for their journey.


The shots used in the final episode and how they tie in with the shots seen in the first episode help close the loop of the story. It all ties a nice little bow on the journey our heroes embarked on. But the way that the episode ends with an opportunity to have these characters come back is fun, but I'm not sure how likely it will be.


It is highly reccommended that you check out this very fun series!

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