Preheat oven to 400.
In a medium saucepan over medium heat, combine sugar, 1/2 cup milk, cream, and butter. Heat until butter is melted and sugar is dissolved, stirring occasionally.
In small bowl, whisk together cornstarch, 2 tablespoons milk, and vanilla.
Pour cornstarch mixture in and remove from heat, whisking constantly to incorporate mixture. Whisk until thickened. Set aside to cool slightly.
Lay pie crust over pie dish and press gently to mold to pie plate. Use a fork to decorate the edges or crimp edges.
Add 1/4 c. cherry pie filling to cream mixture and stir slightly. Pour mixture into pie crust.
Top with remaining cherry pie filling.
Bake at 400 for 20-25 minutes, or until crust is golden brown and pie filling seems fairly set. Remove from oven and let cool completely.
While pie is cooling, make 2 cups fresh whipped cream or let a tub of whipped topping thaw.
When pie is cool, top with whipped cream or whipped topping before serving.