Preheat your oven to 350°F (175°C) to ensure that your cupcakes bake evenly.
Cream together the 1 cup unsalted butter and 1 cup sugar until light and fluffy, about 3-5 minutes with an electric mixer.
Beat in the 4 large eggs, one at a time, ensuring each egg is fully incorporated before adding the next. Stir in the 2 teaspoons of pure vanilla extract.
Whisk together the 2 cups cake flour and 1 tablespoon baking powder in another bowl. Gradually add this mixture to the wet ingredients, alternating with 1 cup whole milk, starting and ending with the flour mixture. Mix until just combined.
Line your cupcake pan with paper liners and fill each liner about two-thirds full with the batter.
Bake in the preheated oven for about 18-20 minutes, or until a toothpick inserted into the center comes out clean. Remove from the oven and allow to cool completely.
In a separate bowl, beat together 8 ounces of softened cream cheese and 4 tablespoons of softened unsalted butter until creamy. Gradually add the 1 pound of confectioners sugar and 2 teaspoons of pure vanilla extract, mixing until smooth.
Once the cupcakes have cooled, generously frost each one with the cream cheese frosting using a spatula or piping bag.
Spoon a generous dollop of cherry pie filling onto the top of each frosted cupcake. Sprinkle with 1 cup coarsely chopped graham cracker crumbs for added texture and flavor.
