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 Sinéad Persaud in particular serving as tour guide for the Salem Witch Dungeon.
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 The Fairly Oddparents Fairly Odder (Especially considering the appearance of her co-star from that show, Audrey Grace Marshall, in the same episode).
Dan Mintz uses the same voice he uses as Tina Belcher in Bob's Burgers.
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. The Tin Can Brothers, who play the Babes, produced the Wayward Guide for the Untrained Eye web series and companion podcast, which centered around (were)wolves and featured the members of Shipwrecked Comedy in its cast.
In "The Heist in the Hotel", Ichabod disguises himself as a priest with a mustache. The mustache is an allusion to Sean Persaud's take on Edgar Allan Poe in Tell-Tale Vlog and Edgar Allan Poe's Murder Mystery Dinner Party, while the priest outfit alludes to his role as Rev. Jeremiah Stillwater in Wayward Guide for the Untrained Eye.
In "Paulie Tahoe", Ryan Garcia (playing a version of himself) wears a MatrixThe Musical t-shirt to his interview with Brom's Babes. This t-shirt is from the Tin Can Brothers' workshop, This Could Be On Broadway, which the real Ryan starred in.
According to TV Insider, this was Matthew Mercer's reason for taking time out of his schedule to play Captain Gravy Davy Crowbones.
According to one Sarah Grace Hart tweet, on her character of Lucretia, "Sean and Sinead wrote a character that basically let me live out all my Sydney Bristow dreams and that my friends, is friendship."
California Doubling: The story takes place in Sleepy Hollow, NY, but filming took place at the Heritage Square Museum in Los Angeles, CA.
Whitney Avalon appears in the background of the trivia scene in Episode 3, and As Herself in a video thumbnail for a Youtube page in Episode 5.
Margie Mintz, Dan Mintz's wife who also cameoed as Agatha Christie in Edgar Allan Poe's Murder Mystery Dinner Party, appears with their children in the open mic audience in "The Secret in the Sea Log", and in the follow-up Unsolved Babesteries episode.
Whitney Avalon exists in the Headless universe, based on the video thumbnails that appear in "The Chaos in Court", while also having a cameo appearance at a Sleepy Hollow trivia night.
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.
Played straight with Christopher Higgins, a contemporary of the 30-something cast playing 15-year-old Trevor Trinkets. Lampshaded by Ichabod pointing out that Trevor looks 30.
Averted with Audrey Grace Marshall, who really was 13 years old while playing a middle school student.
Directed by Cast Member: Curt Mega co-directs the Unsolved Babesteries companion mini-series, which he also plays a featured role in. Sean Persaud co-directs as well, and makes an appearance in one of the episodes.
Mary Kate Wiles plays a secretive, morally-ambiguous antagonist after years of playing earnest, good characters for Shipwrecked (though she previously played a morally ambiguous spy in Tin Can Bros Spies Are Forever). The fact that she is set up as Sean Persaud's love interest (as in previous Shipwrecked works) played on audience expectations.
Felicia Day was quoted by TVInsider saying, “I wanted to channel a badass woman and be the most competent in the room, also stretch myself from who I usually play, more quirky and comedic characters."
Sarah Grace Hart tends to play sweet or shy characters. Here she plays a harsh innkeeper/former Russian spy who is definitely not sweet.
Production Posse: Like other Shipwrecked productions, a number of the actors and crew here have appeared in other Shipwrecked works, have worked with the Shipwrecked crew on other projects, or are simply friends through the acting and web creating community:
Gabe Greenspan, Lauren Lopez, Jimmy Wong, Joanna Sotamura, Julia Cho, Ryan Garcia, Curt Mega, Christopher Higgins, Blake Silver, Tom DeTrinis, and Jon Cozart have all appeared in previous Shipwrecked projects.
The Tin Can Brothers (Joey Richter, Brian Rosenthal, and Corey Lubowich) appear as Brom's Babes, having cast the Shipwrecked crew in their last web series/podcast, Wayward Guide for the Untrained Eye. Corey Dorris also appeared in Wayward Guide, while James Tolbert had a role in the podcast.
Kim Whalen is associated with Richter, Lopez, Dorris, Tolbert, and Rosenthal through her work with Team Starkid.
Matthew Mercer worked with Mary Kate Wiles and Joey Richter on School Of Thrones and Muzzled the Musical back before Critical Role was a streaming show. Ginny Di, Krystina Arielle, and Felicia Day are also established players in the Critter community, with Ginny's popular character cosplays and Krystina's appearance in one of their one shots.
Whitney Avalon and Margie Mintz from Edgar Allan Poe's Murder Mystery Dinner Party both make cameos in the series.
Sean and Tom Lenk had both worked on the 30-Minute MusicalsYouTube channel.
Tom and Felicia Day both featured in the final season of Buffy the Vampire Slayer, with Tom later getting a guest appearance on Felicia's The Guild.
Promoted Fangirl: Ginny Di was a fan of Matthew Mercer's work for years, having followed Critical Role and done cosplays of some of the characters. While the two had previously met at conventions, getting to be scene partners and hang out on set was "an absolute joy" for Ginny.
Sean and Sinead Persaud are siblings, while Sean and Mary Kate Wiles were engaged at the time of filming.
Joey Richter and Lauren Lopez were also engaged at the time of filming.
Curt Mega and Kim Whalen are a married couple playing a married couple.
Dan Mintz's wife Margie appears with their children as Open Mic Audience members during his scene as Bruce McConnell.
Real Life Writes the Hairstyle: While Unsolved Babesteries was meant to take place simultaneously with Headless, by the time Unsolved Babesteries was being filmed, Corey Lubowich had bleached his hair, making him appear with dark hair in certain scenes (and in all of Headless) and bleached hair in others. This is written in as an Actor-Inspired Element, with Corey's character Cal saying his natural hair color is blond and the dark hair in his other scenes is a day wig.
Real Life Writes the Plot: Because Blake Silver was unable to take part in the main Headless series as planned due to travel issues, he was written into Unsolved Babesteries as a character who could show up remotely via laptop. Thus, the plotline of the Babes reconnecting with their old friend, who lives far away.
Special Guest: Tom Lenk and Felicia Day both appear in the finale. Felicia in particular gets And Starring credit for her appearance.
Blake Silver was originally cast as Tom Walker, a main series role and a reference to another Irving short story, "The Devil and Tom Walker". But because of COVID, scheduling, and travel issues, his original role was written out. He instead became part of the Unsolved Babe-steries companion series as Spike.
Jim O'Heir was originally cast as Baltus Van Tassel, but was booked for a pilot before filming could start, with John Rubinstein filling in.
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.
Bonus Material 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).
According to Sean Persaud, the delivery guy from Bookfarters was supposed to appear as an old friend of Max Lee's, but because his appearance derailed the plot too much this was cut.
, this was Matthew Mercer's reason for taking time out of his schedule to play Captain Gravy Davy Crowbones.