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twistedtummies2 · 1 year

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Top 12 Characters from FOX’s Sleepy Hollow

Halloween may have ended the day before yesterday, but I wanted to give the spooky season one last hurrah! I recently did a couple of lists related to characters from Washington Irving’s classic tale “The Legend of Sleepy Hollow.” I’ve been on a Sleepy Hollow kick lately, for a few reasons…and due to this “kick,” I decided it was time to revisit the somewhat controversial FOX TV Series simply called “Sleepy Hollow.” When the show first came out, I actually only got part of the way through Season One before I stopped watching it; at the time, I had a lot of other things eating up my attention, and I think I was also a little more closed-minded towards the drastic reinventions this series put forth.

After revisiting the show in the past couple months, I found a new sort of love and respect for it. It’s not a perfect series, mind you, but I think the mixture of my love of the source material and the excellent performances from the actors, above all else, pull it through. The show is a supernatural crime drama, similar to things like “Supernatural,” “Lucifer,” or “The X-Files.” The series focuses on Ichabod Crane - a dashing Revolutionary War hero, in this version of the story - solving a variety of strange crimes in the modern day. From witches to demons to figures from mythology - and, of course, the Headless Horseman - the show had a lot of really wonderful characters and creatures on display. I decided it would be fun to count down some of my favorite characters from the series overall, in honor of All Hallows Eve (or, given today’s date, Dia de los Muertos; take your pick). Because not only did this show have great reimaginings of the characters from the Washington Irving legend, but also a fine array of original characters unique to this interpretation. They all deserve to be recognized. So, without further ado…here are my personal Top 12 Characters from FOX’s Sleepy Hollow.

12. Jake Wells & Alex Norwood.

These two characters debuted in the show’s fourth and final season. I’m just going to state outright: in my opinion, Season 4 was the worst season of the show. On its own terms, it wasn’t necessarily all that bad, but I think it tried to do a few too many things at once, and changed up the formula of the series in a few too many ways. When you compare to the prior three seasons, it stands out as the weakest link, in my opinion. One of the issues this season had was that it had a whole new cast of major characters we’d never met before, which meant a whole new set of relationships, personalities, and performances for the audience to get used to. Thankfully, most of these characters were pretty strong. Case in point: Jake Wells and Alex Norwood, two eccentric history buffs who work as the chief operatives for Agency 355: a secretive part of the FBI that investigates supernatural phenomenon. Jake and Alex I always saw as a duo, first and foremost, hence why I decided to include them together here. Jake is a dorky, geeky fellow who has read more books on history, and done more research into the paranormal, than almost anyone else; his knowledge on both subjects almost rivals that of Ichabod himself, and he is eager to prove his worth as a hero when he realizes his true calling. Alex, meanwhile, is a snarky, sneaky weapons expert fascinated with ancient technology and cursed objects; she’s actually a bit more skeptical than Jake, but she goes along for the ride. Alex also has a hidden crush on Jake, who naturally remains totally oblivious. These two were just a fun pair to watch in action, and many of the funniest moments in the final season came from their interactions.

11. Jobe.

While Season 4 may have had a lot of problems, one thing I almost unconditionally loved about it was its villains; most notably its two main antagonists. One of those antagonists is Jobe. It’s unclear if “Jobe” is actually his true name or not, but regardless, Jobe is a Mephistophelean sort of figure: a high-ranking demon who has become the personal bodyguard and assistant of the season’s main villain, Malcolm Dreyfuss. Dreyfuss made a deal with the devil years ago, part of that bargain being that Jobe would faithfully serve him until Dreyfuss’ death. However, Dreyfuss’ plans to gain immortality put that exact bargain at risk, and Jobe is thus in danger of potentially becoming a pawn in the mortal man’s game forever. There’s an interesting contrast with Jobe’s relationship with Dreyfuss; Malcolm relies on the demon constantly, and goes to great lengths to help him out, and Jobe will do just about anything Malcolm demands. At times, one could almost believe the two were friendly with each other…but it eventually becomes clear that Jobe is NOT Malcolm’s friend. He’s simply fulfilling the contract’s stipulations to the letter. While he does not approve of the loophole being used, there’s nothing he can really do about it…aside from finding his own loopholes to try and sabotage the scheme.

10. Katrina Van Tassel.

A.k.a. Katrina Crane. In this version, she and Ichabod actually get married, so which surname you use can be interchangeable. I call her “Van Tassel” simply because that’s the character’s name in the original story. ANYWAY: Katrina was a major figure in the first two seasons of the show; in many ways, she is the catalyst for a lot of the action that goes on in the series. It’s revealed that Katrina is a witch who was secretly working with American Revolutionaries. It was partially due to her influence that Ichabod defected from the British side of the conflict, and the two were eventually wed. For the first season and a half, Katrina is one of the main protagonists…but, in the latter part of season two - for various reasons - the character falls to the dark side, going from a good and noble enchantress to a truly wicked witch. I’ve always felt sort of conflicted about this portrayal of Katrina; my biggest issue is that, for that first season and a half, the writers couldn’t seem to make up their minds if Katrina was meant to be a strong, independent, powerful woman and role model…or a rather silly damsel in distress. On the one hand, she’s quite literally got a ton of power as a witch, and she’s a skilled manipulator in her own way…but on the other hand, most of her time before we get to her descending arc is spent with Ichabod trying to save her, and it gets old fast. Having said that, I honestly think she became a much more interesting character in the second half of season two, with her descent into darkness story arc; the tension of love and anger between herself and Ichabod, not to mention the other characters, made for some dramatic moments, and her motivations and goals as an antagonist were really quite interesting. She got more chances to actually SHOW her strength as a character, helping Ichabod on cases in the early parts of Season 2B, and then shifting and turning her coat as the arc went on. Actress Katia Winter really helps sell the character, and while I may have some issues with the way she’s written, she’s still an important and iconic figure in the series.

9. Diana Thomas.

Yet another character from Season 4. Played by Janina Gavankar, Diana had a really tough gig to follow: for the first three seasons, the two main characters of the show had been Ichabod Crane and “Leftenant” Abbie Mills. However, due to issues with the creative team behind the scenes, Nicole Baharie - Abbie’s actress - decided it was time to leave the show. Rather than end the series with Abbie’s death, however, the writers decided to provide Ichabod with a new modern detective to join forces with, and invent a new “Second Witness” as well. This is where Agent Diana Thomas of the FBI comes in: much like Abbie, she meets Ichabod when her own partner and her boss end up killed by a demonic entity. From that point on, the two become entangled, as Ichabod helps Agent Thomas with a variety of cases not in Sleepy Hollow, but in Washington D.C. itself. At first, we believe that Diana must be the new Second Witness…but instead, it’s revealed that Diana is a mother, and it’s her ten year old daughter, Molly, who is the Second Witness. Diana effectively tries to become a crusader for her own offspring, fighting the battles Molly is too young to fight, and trying to find some way to balance her duties as a mother, a member of law enforcement, and part of a secret war against Hell itself all together. While following on the heels of “The Leftenant” wasn’t exactly an easy task, I actually think Diana pulls it off: her own relationship with Ichabod hits some of the same beats, but her character and setup is unique enough to make her interesting and fun in her own right. The way things develop between herself, Molly, and Ichabod is also quite engaging; if the show had gone on longer, she might have ranked more highly here.

8. Nick Hawley.

It’s weird that this character ranks so highly for me, because - much like the Season 4 cast - this was a character who only appeared for a single season. And unlike most of the S4 cast I’m covering here, he WASN’T a series main during his tenure. I guess one could just argue that character is simply that strong. Nick Hawley, a.k.a. “The Privateer” (as Ichabod likes to call him), is a self-proclaimed treasure hunter. He seeks out rare and mysterious artifacts and items, which usually have some kind of supernatural or mythological tale behind them, and then sells them off either to private buyers or simply to the highest bidder he can find. Hawley is a modern-day pirate: while not completely without scruples, he cares most chiefly about his own health and finances, which makes him an unpredictable, anti-heroic figure for the season. He’s smart, he’s capable, and he’s a great ally to have when you have him…but he’s not above leaving people behind in the lurch when it suits him best, and he even acted as an enemy once or twice to the main heroes, whenever his clients weren’t exactly friendly souls. He was a major figure in Season 2, and he got richer and richer as the season went on…but unfortunately, this was the only season Hawley appeared in. His story effectively remains unfinished, since his departure from the show saw him planning to actively hunt down his own adoptive mother (who had become a demon…it happens). We never saw Hawley again, so we have no idea how his adventures on that front turned out. I had a feeling they MIGHT have been considering using the character in future seasons, but for one reason or another that never happened, either because the show was canceled before such a thing could occur, or because the actor just wasn’t available. Whatever the case, he was a fun figure who brought a sense of mercenary chaos to the program, and his time in the series, while short, was truly unforgettable.

7. Malcolm Dreyfuss.

Like I said, in my opinion, the best part of Season 4 had to be the villains. Chiefest among them is Malcolm Dreyfuss, the main antagonist for the show’s final season arc. Dreyfuss is a character who feels like something straight out of a comic book, and I mean that in the best possible way: he’s an eccentric, half-mad tech mogul, with a flamboyant, sleazy sort of personality. He feels like he’s somewhere between a mad scientist and a used car salesman. It was a unique personality for a main villain in the show to have; most of the main villains before were more serious, stoic, sinister characters; hyper-powerful beings who controlled legions of Hellspawn and could kill you with a look. Dreyfuss is the exact opposite: he’s just a guy. A very, VERY bad guy with a lot of ambition and a lot of money. In fact, at times Dreyfuss is quite pathetic; one of my favorite elements of this character is that, despite all his theatricality and high-flying schemes of grandeur, there are so many times where the vulnerability and fearful status of Dreyfuss’ position comes into play. Whenever someone sees right through him, so to speak, he goes from a criminal mastermind to a whimpering child, and it’s equal parts funny and kind of sad to see this character fall so low. While he’s an awful creature, he’s also highly entertaining, and his reasons for his evil deeds are actually somewhat sympathetic: this is a man who lived his life in the shadows for so long, and desires to finally be in the spotlight. I think that’s a concept we can all relate to. The season as a whole may not have been the best, but Dreyfuss is a great villain who made for some of the most memorable moments in the final arc of the show.

6. Frank Irving.

Played by the inimitable Orlando Jones, Captain Frank Irving was one of the main characters in the first two seasons; I can’t help but wonder whether or not it’s merely coincidence that, in my opinion, the latter two seasons - where he was NOT present - were the least grand of the series as a whole. In any case, Irving, for the first half of season one, starts off as a pretty standard sort of “doubting police official” character. While he isn’t a bad person, he doubts in all of the supernatural and fantastical explanations Ichabod and Abbie try to give him for the various crimes they face. It isn’t until his own close encounter with the Headless Horseman that Captain Irving becomes a more active member of the team, as he realizes the war with evil is very real, and far more bizarre than he ever gave it credit. That war hits close to home when a demon actually possesses his daughter; an event that causes endless dismay for Irving, and sets in motion many of the struggles he faces for the rest of his time in the show. Seeing Captain Irving’s transition from a tough-as-nails doubter to an increasingly more tragic and complex character entangled in a web of danger made for an interesting story arc. The lengths he’ll go to in order to keep his family safe are only matched by his tenacity on the battlefield, and the many twists and turns his own private side of the story faced made for some of the most intense parts of the show. It’s really a shame that, after Season 2, we never saw him again, or even got much mention of where he was and what was going on in his life.

5. Henry Parrish.

Played by the Scarecrow himself, John Noble (or Denethor himself, for you Lord of the Rings fans), Henry Parrish was one of the main antagonists in the first two seasons of Sleepy Hollow. In fact, in Season 2, he basically acted as the main villain, outranking even the Headless Horseman himself! When we first meet Henry, he is a somewhat neurotic, mild-mannered fellow, suffering under a great burden: Henry is a Sin Eater, someone who can physically absorb people’s sins into his own body, a fact that seems to torment him constantly. As the series goes on, he comes out more and more as a worthy ally to the main team…but it’s ultimately revealed that Henry is actually the master manipulator behind many of the things that have gone wrong in the season up to that point. Henry, you see, is actually Ichabod’s own son, Jeremy Crane; abandoned by his mother as a child while Ichabod was still in the crane, Jeremy grew up hated and feared, and was eventually - like Ichabod himself - buried in a state of suspended animation, only to be reawakened years later, and years before his father (hence why the son is physically older than the father; he’s had more time to age). But while Ichabod rose from the dead as a force for good, Jeremy - renaming himself “Henry Parrish” - has become a force for evil: he is the Horseman of War, one of the Four Horsemen of the Apocalypse, and a servant of the arch-demon Moloch, whom he sees as his “real” father. John Noble plays the character to perfection, and despite his ultimate defeat in Season 2, Henry would actually be one of the few characters to see the show to the end: he returned a few times in Season 4, first in a nightmare Ichabod has while under the influence of a monster, and then for real in the last couple episodes of the show, teaming up with Malcolm Dreyfuss, as well as hiss old compatriot, the Headless Horseman. Speaking of…

4. The Headless Horseman.

I mean…it’s Sleepy Hollow. So of COURSE the Headless Horseman is going to be in the Top 5 here. In fact, some of you are probably wondering why the Horseman isn’t in the Top Three! How could the HEADLESS HORSEMAN not make the top three in SLEEPY HOLLOW?! Well…I’ll get to that in a bit, but first, let’s go over the positives. In this series, the Horseman is revealed to be another of the Four Horsemen of the Apocalypse: specifically, he is the Horseman of Death. And, being the Horseman of Death, he cannot truly die, no matter what happens. As a result of this, even as other villains came and went throughout the show, the Horseman stuck around: alongside Ichabod and Jenny Mills (more on them later), the Headless Horseman is the ONLY major character in the series who appears in all three seasons. While he didn’t show up in every single episode, every time the Horseman DID appear, it was a big deal, which made his appearances all the more special; you knew bad stuff was going down in the Hollow when Death rode into town. I also appreciate that the series actually went out of its way to make the Horseman a real character, with a proper true identity, backstory, and personality…at least at first. This is where the problem with the Horseman, and why he isn’t in the top three, comes into play: in the first two seasons, the Horseman is handled EXTREMELY well…but in Season 3, the character only appeared twice. First in a cameo in the opening…and then in a more prominent part in the season finale. That’s it! We never see or even get much reference to him anywhere else! In a show called SLEEPY HOLLOW, it was kind of shocking that such an iconic figure was almost nowhere to be found, especially after his huge level of importance in the prior two seasons. In Season 4, the character had a more prominent role - acting as a tertiary antagonist after Malcolm and Jobe, with at least as many appearances as he had in Season 1 - but the actual character took a HUGE step back. He basically just became a faceless monster; that’s not necessarily a bad thing, since most versions of the Horseman are that, but a big part of what made the first two seasons and their handling of the Horseman so great was that they DID give him more real character and development. Season 4 really watered down the character, and felt like a missed opportunity as a result. There were lots of places where all that established lore and personality could have been utilized, and it just never really was. Having said all that…it was still really cool to see the Horseman anytime he appeared, and the fact he lasted till the end is definitely a credit to the ghost’s power. Also, I guess one CAN technically say he was in EVERY episode, since the opening titles for every season featured the Horseman…but I think that’s pushing it a bit. Anyway, great version of this classic horror icon, and easily my favorite villain from the series…but not great enough, within the show’s own setup, to make the top three.

3. Abbie Mills.

Abbie Mills, a.k.a. “The Leftenant,” was the secondary protagonist of Sleepy Hollow for the first three seasons. And unlike with Captain Irving, it’s no coincidence at all that the show’s biggest decline happened courtesy of her departure. Abbie is an ambitious police officer at the start of the show, with a checkered past; as a child, she encountered supernatural evil at a young age, something she has tried to deny all her life. Tragic events in her past led Abbie to becoming a petty thief, but - with the help of her mentor, Sheriff August Corbin - she eventually found her calling in law enforcement. In Season 3, Abbie went from being a simple police lieutenant to an agent of the FBI, stationed in New York, which kept her close to home, so to speak, while still allowing the character to advance and shake up the formula a bit. Abbie was a fun character; her relationship with Ichabod was one of purest friendship. There is no romance between them, yet they are as close as two human beings can be; as Ichabod describes in the “Bones” crossover episode (yes, that was a thing), they are a relationship of pure opposites. Ichabod is a quirky, theatrical, grandiose figure out of place and out of time, given to grandiloquent phrases and speeches and constantly prattling off trivia about a past he lived; Abbie is a more down-to-Earth, grounded person who takes things more easily in her stride, but is still open to having her horizons broadened. Both often feel alone in the world, due to various personal tragedies they’ve faced and mysteries they have yet to figure out, but at the end of the day, they always have each other. At times they may bicker and banter, but the chemistry between them is pure gold. When “The Leftenant” finally did leave the show, she went out like a hero - sacrificing everything to save her friends, her family, and the world itself - which was just the proper sendoff her character deserved. One only wishes she never had to leave at all.

2. Jenny Mills.

While Jenny Mills was never the secondary protagonist in ANY season, she was, effectively, the tertiary protagonist of EVERY season. Like I said before, she was one of only three major characters in the show to appear in every single season, practically from start to finish. (The only other two were Ichabod Crane and the Headless Horseman, and…let’s face it, in a show called “Sleepy Hollow,” it would have been more amazing if those two DIDN’T show up every single season.) At the start of the show, Jenny is Abbie’s estranged sister; a notorious delinquent who has spent much of her life in-and-out of the local mental hospital. It’s later revealed that all that time “out” of the hospital was spent with Jenny running various secret missions for Sheriff Corbin, who knew all along that the Apocalypse was night, and helped Jenny out when she was possessed by a demon during her adventures. As the show goes on, Jenny became a more and more interesting and important character, and even after Abbie and so many other characters who had played such a big part in the series for the first three seasons disappeared, Jenny stayed on right to the last episode. Jenny is just a bad@$$, plain and simple: she’s not as straight-laced as her sister, much more trigger-happy and far less lawful. She’s essentially a treasure hunter; a low-budget Indiana Jones who works from a trailer rather than a university. In many ways, she is a lot like Nick Hawley; but while Hawley fights for himself above all other things, Jenny believes in a bigger plan, and is simply trying to find her place in it. Because she lasted so long in the series, we got to see Jenny interact with more characters and form more relationships than almost any other in the show, barring Ichabod himself; and as the show progressed, and her role increased, we saw Jenny mature and become more and more independent. The final season indicated that she was actually planning to leave “Team Witness” and go off on her own, no doubt preluding the actress’ departure; I’m actually sort of glad this DIDN’T happen, only because it meant that the character did remain a firm anchor all the way to the end of the ride. Having said that, it would have been interesting to see how Jenny and the show would have fared if this had; this is a character so strong that I actually would have loved to see an entire series JUST about her, and that’s high praise indeed.

1. Ichabod Crane.

For some, it’s probably an obvious no brainer to put the main character at the top of the ranks. However, in all honesty, I would argue it’s more surprising to do so, since - as we all know - the MAIN character of any series isn’t necessarily one’s FAVORITE, nor the BEST. But in the case of “Sleepy Hollow”...there is no question, this is just a case where the central protagonist is my favorite. I think a lot of the credit goes to the actor, Tom Mison: while the character he plays owes precious little to Washington Irving’s spindly schoolmaster, something about the personality he gives Ichabod, and the way Mison looks, in general, just feels so much like it captures the basic DNA of the character we all know and love, while adding something brand new and utterly fascinating to the mix. Much of the humor from the series comes from Ichabod’s “fish out of water” status - a man from a past long-misunderstood, stuck in a future-present he is still struggling to fully understand. At the same time, much of the pathos for the character comes from the same place: a constant theme in the series is Ichabod constantly battling between the sense of being alone in the universe, and realizing that maybe he isn’t AS alone as he really thinks. Throughout the series, he loses allies, friends, family, and even loved ones…but through it all, he perseveres, and finds new people to assist him, as well as new enemies to combat. There is never a dull moment when Ichabod is onscreen, and that’s thankfully most of the show’s runtime, given his status as the main character. He is by no means my definitive take on the classic character, but he is a strong and interesting protagonist in his own right, and it’s easy to see why, when all else failed, you could count on Ichabod to keep people coming back to the show, over and over again. It’s really not a shock at all that Ichabod Crane is My Favorite Character from FOX’s Sleepy Hollow.

Honorable Mentions…

Sheriff August Corbin. (He’s played by Clancy Brown. ‘Nuff said.)

George Washington.

Benjamin Franklin.

Andy Brooks.

Betsy Ross.

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