Halloweentown Fancast – Halloween Special!

“Halloween is cool!”

It is the line that immediately comes to mind when I think of the highly successful and beloved 1998 Disney Channel Original Movie Halloweentown. I was only a 2 year old little jelly roll when this movie was released, but its place as a cornerstone of Disney Channel Original Movies was cemented into my mind as young as 4 years of age.

Nearly 20 years later, Halloweentown still maintains its place as a must-watch film for that spooky time of year when the air finally chills and there are horrifyingly delightful orange and black decorations everywhere you look. Halloween is the fun precursor to the holiday season. But, as with most of our childhood classic films, I can’t help but wonder how fun and interesting a Halloweentown reboot on, say, Freeform might be. So, without further ado, I’ll present my favorite choices for a reboot of Halloweentown for a new generation.


First off is legendary grandma and iconic queen Aggie Cromwell. Aggie is Marnie, Sophie, and Dylan Piper’s grandmother and is also a witch who lives in Halloweentown. Previously portrayed by acting legend Debbie Reynolds, it seems only right that another legend play her in a reboot. Who better than Cicely Tyson? With an illustrious acting career that spans decades, she is more than capable of playing the fun and exciting witch that is Aggie Cromwell.

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Cicely Tyson as Aggie Cromwell

Next up is Gwen Piper, daughter of Aggie and mother to Marnie, Dylan, and Sophie. Having previously been born a witch in Halloweentown, Gwen moved to the mortal world and gave up being a witch after marrying her mortal husband. As Marnie, Dylan, and Sophie grow older, Gwen keeps Halloweentown a secret from them and attempts to keep them from celebrating Halloween until Aggie comes for her annual Halloween visit. As the movies go on, Gwen grows to be a powerful witch and uses her magic more often after the first Halloweentown movie. Suits alum Gina Torres would be best for this role as she has the capability of portraying a formidable witch and loving mother.

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Gina Torres as Gwen Piper

Next is the main protagonist for the Halloweentown movie: Marnie Piper. She is Aggie’s granddaughter, Gwen’s daughter, and oldest sister to Dylan and Sophie. Marnie is a strong-willed and intelligent young witch. Her bright and curious personality are prevalent in her character and Black-ish actress Yara Shahidi would be the best person for this role in a reboot. When I first thought about a reboot, I immediately pictured Yara saying that iconic line that always came to mind when thinking of this movie: “Halloween is cool!”

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Yara Shahidi as Marnie Piper

Dylan Piper is Marnie’s younger brother, Gwen’s only son, and Aggie Cromwell’s grandson. He is generally portrayed as a bookish nerd, valuing school and grades over just about everything. Like his mother, he is adverse to magic and Halloween and views magic skeptically even though he himself is a warlock. In the first Halloweentown movie, Dylan is about 12 years old. For this role, Stranger Things’ Caleb McLaughlin would be perfect.

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Caleb McLaughlin as Dylan Piper

Sophie Piper is the youngest of the Piper siblings. Able to do simple spells, she later shows herself to be just as powerful as her sister, mother, and grandmother. Sophie is amazing at remembering spells and conjuring things and also has notable skill in precognitive abilities. Even though Sophie is supposed to be 7 years old in Halloweentown, there is definitely some room to age her character up to 8 or 9 years old. For this role, newcomer Chanicka Culcleasure would be an awesome fit.

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Chanicka Culcleasure as Sophie Piper

Kalabar is the primary antagonist for the first Halloweentown film and is also an ex-boyfriend of Gwen Piper. Resentful of the fact that Gwen left him to be with a human, Kalabar, previously Mayor of Halloweentown, despises humans and doesn’t like that the Cromwell magic remains so powerful in Halloweentown. He attempts to rally the citizens into taking over the mortal world but is defeated by the Cromwell family. For this role, Giancarlo Esposito would be perfect.

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Giancarlo Esposito as Kalabar

Next is Luke, a friend of Marnie and resident of Halloweentown. He is originally a goblin, though Kalabar briefly turns him into a human. One Kalabar is defeated he reverts to his original form. He has a crush on Marnie for the first two films. For this role, I imagined KJ Apa of CW’s Riverdale.

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KJ Apa as Luke

Finally, we have the iconic and hilarious character of Benny Deadman, a taxi-driver who just happens to be a skeleton. He offers comic relief in the film and is a staple of Halloweentown. He briefly turns against the Cromwells while under the influence of Kalabar’s magic but goes back to normal after Kalabar’s death. For this role, I pictured a distinct and funny voice. The best actor for this character is none other than Christopher Walken.

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Christopher Walken as Benny

So what do you think? Who would you like to see in a reboot of Halloweentown?

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