A mixed Halloween bag (Spoilers)
The Jester (2023) and The Jester 2 are both based on a trilogy of short films, all directed by Colin Krawchuk and starring Michael Sheffield. Each installment is about a sinister entity that’s traded the classic jester outfit for a snazzy orange suit and top hat. If I were the Jester (Sheffield), I would have gone with a coat borrowed from James Dean and a thorny crown, but to each his own.
The Jester (2023)

The first full-length film follows Emma (Lelia Symington), a young woman whose father, John (Matt Servitto), abandoned her when she was young. Much to Emma’s chagrin, John then went on to start a new family and had another daughter, Jocelyn (Delaney White), also known as JC. After the Jester kills John, the half-sisters both find themselves in the creature’s crosshairs.
It was smart of the filmmakers to give this movie an emotional core. Unfortunately, it falls flat, primarily because of lackluster acting. There’s a scene where Emma delivers a lengthy monologue about her relationship with John and her conflicting emotions regarding his death. The entire time I was watching that, I was thinking, ‘I don’t believe you.’ Jocelyn has a similar moment where she laments how alone she is, and it’s better, but not by much.
The film climaxes with Jocelyn being badly injured. Emma tells the Jester he can do what he wants to her, but to stay away from Jocelyn. And then the Jester leaves. What? So, what this movie is going for is the scene at the end of the original A Nightmare on Elm Street, where Nancy (Heather Langenkamp) takes back all the power (spoilers) she’s given Freddy (Robert Englund). But that worked because Freddy had rules and stood for something.
The Jester’s power seems limitless, and what he is supposed to represent isn’t clear. Emma refers to him as a sickness and then, when visiting John’s grave, says that John had a sickness that he passed down to her. So, there’s clearly supposed to be some parallel going on, but I can’t figure out what it is. Selfishness, being closed off to other people, or something else entirely.
The Jester and dead dad/estranged sisters plots don’t come together well. This movie’s other issues—bad acting and weak mythology—are extensions of that one problem. That said, there are a few things about this movie that I do like. Sheffield is solid as the Jester, and some of his antics, like his top hat eating a dude’s head, were well done.
The Jester 2

This sequel is about a 15-year-old magician named Max (Kaitlyn Trentham) who’s shy and ostracized. Her family’s not there for her. The people she goes to school with bully her. Her only friend seems to be Willie (Dingani Beza), an older magic shop owner. So, when the Jester offers to go trick-or-treating with her, she happily accepts, even though he’s a creepy stranger and a weirdo who doesn’t talk. Something she quickly regrets when the Jester starts murdering people.
This installment finally gives us a backstory for the Jester. He sold his soul to the Observer, implied to be the devil. Now, on Halloween, he needs to perform a magic trick for four people before sacrificing them, though he’ll also kill people just for fun. Only now, Max needs to perform the trick before he can sacrifice, for reasons that are so convoluted and poorly explained that I need to watch this movie again before I can even try to explain any further.
In a behind-the-scenes featurette, Krawchuk said one of the inspirations for this sequel was Collateral. If you haven’t seen that film, it’s about two very different guys. A taxi driver named Max (Jamie Foxx) gets roped into assisting a hitman named Vincent (Tom Cruise) in carrying out his assignment, and you kind of wish they could be friends. Applying that dynamic between a slasher and final girl is a really interesting idea, and I don’t think it’s been done before.
The Jester 2 is definitely an improvement. I believed Trentham as her character, even though she was clearly not 15, and the ending is much more satisfying. However, much like the preceding film, it doesn’t quite live up to its full potential. I actually had to think for a while about why I didn’t love this movie. It has all the right ingredients, and I wanted to like it. What I’ve come up with is that it doesn’t go far enough.
I don’t just mean the kills. The film could have done more with a magical jester, but budgetary limitations were a factor. More could have been done character-wise. Max’s family appears in only a single scene before the climax, so I didn’t really care when the Jester inevitably attacked them to get to her. This film could have also utilized the sweet relationship between Max and Willie more effectively, as he only appears in two scenes.
Conclusion

Overall, everything The Jester (2023) and The Jester 2 do, the Terrifier series does better. However, both films do have their bright spots. Beyond what I’ve already said, both movies look great for low-budget indies, and the passion that Krawchuk, Sheffield, and co. have for the material is obvious. I recommend checking out the Jester shorts, available on YouTube, and giving the full-length movies a try—especially the second one.