Place parchment paper over the pie crust and place pie weights or dried beans over the bottom of the pie crust.
Bake for 20 to 30 minutes or until the pie crust is cooked through and golden. Make the cherry filling while the crust is baking.
Lift the parchment and remove the pie weights or beans. Set the pie crust aside to cool completely.
Make Cherry Filling
Melt 2 tablespoon butter in a large saute pan or skillet over medium heat.
2 tbsp butter
When the butter has melted, add 2 tablespoon flour and whisk to combine with the butter.
2 tbsp all purpose flour
Cook the butter and flour mixture, whisking frequently, for about 2 minutes until lightly golden.
Add the cherries and 2 tablespoon sugar. Stir to combine.
1 16 oz bag of frozen dark sweet cherries, 2 tbsp sugar
Cook for 5 minutes, stirring occasionally.
Cover and reduce heat to low. Cook for another 20 minutes, stirring about every 5 minutes. By the end of the 20 minutes, the filling should resemble a pie filling.
Transfer filling to a bowl and let cool to room temperature. (Can put in the fridge to speed along, but getting it too cold can affect how easy it is to spread when it comes time to assemble the pie.)
Make Chocolate Filling
Beat chocolate pudding mix with 1 ¾ cup milk and ¼ cup heavy cream for 2 minutes (or time on package, if different).
1 box instant chocolate fudge pudding mix, 1 ¾ cup milk, ¼ cup heavy cream
Chill for 5 minutes to set.
Make Whipped Topping
Beat 1 cup heavy cream, 2 tablespoon powdered sugar, and ½ teaspoon vanilla on medium-high (#4 if using a KitchenAid stand mixer) for about 4 minutes or until it holds a whipped cream shape. Be careful not to whip for too long.
1½ cups heavy cream
Assemble the Pie
Pour chocolate pudding mixture into the pie crust. Add cherry filling on top of the chocolate. Top with the whipped cream (whipped cream should cover the whole pie).
1 tsp vanilla, ¼ cup powdered sugar
Store covered in the refrigerator until serving.
Notes
SubstitutionsIf you can only find cook and serve pudding mix, prepare it according to the package instructions using the amounts of milk and heavy cream in this recipe. Chill before adding to the pie. Can substitute a can of cherry pie filling, but instead of using whole can of filling as-is, use tongs or a fork to pick out the cherries when adding to the pie. Add “goo” from the pie filling can as needed. Using all of the goo usually is a bit too much for this pie. You want the filling to be a thin covering to the chocolate layer.Can substitute store-bought whipped topping (e.g., Cool Whip) or whipped cream.