Preheat oven to 350°F. Line 24 cupcake tins with liners and set aside.
In the bowl of your mixer, beat cake mix, instant pudding, milk, vegetable oil, and eggs on low speed for 30 seconds.
Scrape the sides of the mixing bowl and beat on medium speed for two minutes.
Fill prepared cupcake tins 2/3 full.
Wipe out your mixing bowl, then beat cream cheese and granulated sugar until smooth.
Scrape the bowl and beat in the egg and vanilla until smooth.
Spoon a heaping teaspoon of the cream cheese mixture on top of each batter-filled tin.
Bake cupcakes until they are golden and spring back when lightly touched in the center, about 20 minutes.
Remove from oven and let cool for 5 minutes in pan before removing from pan to cool completely on wire rack.
In the bowl of your mixer, beat pudding mix and heavy cream with your mixer’s whisk attachment on medium low until it begins to thicken. Increase speed to high and beat until thick – it should form stiff peaks when a spoon is pulled through it.
Generously frost cupcakes, then roll the frosting gently through graham cracker crumbs and top with a spoonful of cherry pie filling.