On September 20, 2026
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Cast of Chalk It Up
21 credited roles
Maddy Curley
Apple
John DeLuca
Chet
Julie Warner
Dean York
Drew Seeley
Todd
Tarah Paige
Emily
Rachele Brooke Smith
Angelina
Thomas Fowler
Preston Kelly
Svetlana Boguinskaia
Coach Baryshova
Molly Gardner
Tanya
Nikki SooHoo
Cali
Nicholas Gonzalez
CIA Interviewer
KJ
Krista Jasper
Cashew
JH
Jen Hansen
Becky
David Wilson Page
Mike
CG
Cecile Garcia
Skylar
MV
Meghan Victoria Martin
Penny
Jeremy Gimenez
Chelsey
Brittnee Habbib
Courtney
Anton Narinskiy
Jake (proposing man)
Ashley Ledbetter
Ashlie (fiancée)
Elizabeth Sandy
Apple's Mom (voice)
