Preheat and prepare the dish. Preheat your oven to 350 degrees F (about 175 degrees C). Lightly spray the bottom of a 13 × 9‑inch baking dish with nonstick spray.

Make the crust. In a medium bowl, combine 3 1/4 cups of the Oreo cookie crumbs with the melted butter. Mix until the crumbs are evenly moistened. Press this mixture firmly into the bottom of the prepared baking dish to form a compact crust. Reserve the remaining 1/4 cup of crumbs for garnish later.

Bake the crust. Place the dish into the oven and bake for about 15 minutes, or until the crust is set and slightly firm. Remove from oven and allow to cool completely.

Prepare the cream cheese layer. In a medium bowl, use an electric mixer to beat together the softened cream cheese and the powdered sugar. Mix for about 2 minutes or until the mixture is fluffy and smooth.

Add whipped topping. To the cream cheese mixture, add one 8‑oz container of whipped topping. Gently fold or beat until everything is combined and smooth. Evenly distribute the cream cheese mixture over the cooled crust.

Add the cherry layer. Spread both cans of cherry pie filling over the cream cheese layer in an even layer so cherries cover the cream cheese thoroughly.

Make the chocolate pudding layer. In another medium bowl, whisk together the two packages of instant chocolate fudge pudding mix with the whole milk and the almond extract. Use an electric mixer if needed to ensure it becomes thick but still pourable. Once smooth, pour or spread the pudding layer over the cherries.

Frost with whipped topping. Take the remaining two 8‑oz containers of whipped topping (or only one if you prefer a thinner top) and frost the top of the pudding layer. Spread it evenly to create a light creamy cap.

Garnish. Sprinkle the reserved 1/4 cup of crushed Oreo crumbs over the whipped topping. Then grate some chocolate over the top, and place a few maraschino cherries for a classic decorative touch.

Chill. Cover the dish and chill in the refrigerator for at least 4 to 6 hours, or preferably overnight. Chilling allows the layers to set properly and the flavors to meld, giving you clean slices and a fully cohesive dessert when you cut and serve.