Prepare the Cookies:
Preheat the oven to 350°F (175°C). Line a baking sheet with parchment paper.
Using a food processor, grind the Oreo cookies into fine crumbs. In a medium bowl, combine the crushed Oreos, flour, corn starch, black cocoa powder, baking soda, baking powder, and salt. Set aside.
In a stand mixer, cream the softened butter, granulated sugar, and brown sugar until light and fluffy. Add the egg and vanilla extract, and mix until well combined, scraping the bowl as needed.
Gradually add the dry ingredients to the wet mixture, mixing until just combined.
Using a large cookie scoop, portion the dough into 8 equal-sized balls. Flatten each ball to about 1 inch in thickness and place them on the prepared baking sheet.
Bake for 10 minutes. After removing from the oven, use a ⅓ cup measuring cup to gently press down the center of each cookie, creating a “pie crust” shape. Let the cookies cool completely.
Make the Chocolate Silk Pie Filling:
In a large bowl, use a hand mixer or stand mixer to combine the chocolate pudding mix, milk, heavy cream, powdered sugar, and vanilla extract. Beat until thick and fluffy.
Pour in the melted chocolate and mix again until smooth. Spoon the chocolate filling into the cooled cookie “pie crusts.”
Make the Whipped Cream (optional):
In a clean, chilled bowl, whip the heavy cream, powdered sugar, and vanilla extract until stiff peaks form.
Top each cookie with a dollop of whipped cream and garnish with chocolate curls or shavings for an extra touch of elegance.
Serve:
Enjoy these decadent French Silk Pie Cookies as a delightful dessert!