Preheat oven to 350 degrees F. Place 12 foil cupcake liners in a cupcake pan. Lightly coat the foil liners with nonstick cooking spray.
Prepare brownie mix with oil, water, and eggs, according to package directions. Set aside.
Use an electric mixer to combine cream cheese, sugar, egg, and vanilla extract in a medium mixing bowl. Beat until blended and smooth. Set aside.
Divide the prepared brownie batter between the foil liners. Each cupcake liner will be about ⅔ full. Spoon about a tablespoon of the cheesecake topping over the top of the brownie batter in each liner. Spoon a tablespoon of cherry pie filling, including 2 or 3 cherries, on the center of the cheesecake topping. You will not need the entire can of pie filling. Run a toothpick through the cheesecake and cherries to create a light swirl pattern.
Bake for 24 to 26 minutes.
Cool completely and then chill for 3 or 4 hours to allow the cheesecake to set up.
Cupcakes taste better chilled. Store covered in the refrigerator for 3 to 4 days.