Set up your workspace with all ingredients and tools within easy reach. Crush the cookies into fine crumbs using a food processor or by placing them in a bag and smashing with a rolling pin.
Mix the crushed cookies with softened cream cheese until well combined and the mixture feels sticky and dough-like when pressed.
Use a cookie scoop or spoon to portion out small balls, about the size of a walnut, and roll them gently between your palms. Insert a stick into each ball to create the cake pop handle.
Place the shaped cake pops on a cooling rack and chill in the refrigerator for at least 30 minutes until firm and chilled through.
While the cake pops chill, melt the chocolate along with a tablespoon of oil or shortening in a double boiler or microwave, stirring until smooth and glossy. Be careful not to overheat to prevent burning.
Dip each chilled cake pop carefully into the melted chocolate, turning gently to coat evenly. Tap off excess chocolate gently against the side of the bowl.
Decorate immediately with sprinkles, edible glitter, or spooky details like tiny fangs or candy eyes while the chocolate is still wet and shiny.
Place the decorated cake pops on the cooling rack and allow the chocolate to set at room temperature, about 15-20 minutes, until they are firm and glossy.
Once set, serve your spooky cake pops on a platter and enjoy their crunch and sweetness, perfect for Halloween festivities!
