Add the cookies into the food processor. Pulse until the cookies are all a fine crumb. If you don't have a food processor, add them into a storage bag and crush them with a rolling pin into a fine crumb.
Add in the sugar and melted butter and stir until the crumbs are coated with butter.
Press the crumbs firmly into a 9x13 glass pan. Place in the fridge to chill while working on the next layers.
In a microwave-safe bowl, add in the milk chocolate chips and heavy cream. Microwave in 30-second intervals and stirring after each interval until the ganache is smooth. Place into the freezer for 10 - 15 minutes while making the cream cheese layer.
In a medium mixing bowl, add the cream cheese. Using a hand mixer, beat until creamy.
Add the sugar, vanilla, and butter. Beat on medium until incorporated. Scrape down the sides and beat in any remaining bits. Set aside.
In a separate bowl, add in the heavy cream. Beat on medium speed until soft peaks form.
Add in the powdered sugar and beat until stiff peaks form.
Fold the whipped cream into the cream cheese mixture until combined.
Add dollops of the cream cheese all over the crust. Using an off-set spatula, spread the cream cheese out evenly and to the edges.
Drizzle the chocolate syrup on top of the cream cheese. Using a toothpick, make swirls into the cream cheese being careful not to disturb the crust. I didn't mix all of the chocolate syrup in, a lot of it sat on top.
Pour the chilled ganache on top of the cream cheese and spread it to the edges.
In the bowl you used for the cream cheese mixture, add in the pudding mix and milk, Whisk until thickened, about 2 minutes.
Pour the pudding on top of the ganache. Try to pour close to the sides of the pan to help prevent the ganache from being pushed to the side. Spread the pudding out evenly and to the edges.
In the bowl you used previously for heavy cream, add in the 2 cups of heavy cream. Beat until soft peaks form.
Add the powdered sugar and vanilla extract. Beat until stiff peaks form.
Add dollops of whipped cream on top of the pudding. Spread it out evenly.
Add the chocolate syrup in a sandwich bag. Cut out a very small hole in one of the corners. Draw a criss-cross pattern on the top of the whipped cream. Sprinkle chocolate curls on top.
Place in the fridge and chill until the pudding has time to firm up. (I let mine chill overnight.) Cut into 15 pieces and serve.