Bring the cream cheese to room temperature so it is fully softened. Place it in a large mixing bowl with the powdered sugar and vanilla extract, then beat until creamy and completely smooth.

Add the thawed whipped topping to the cream cheese mixture. Fold gently with a spatula until the mixture is evenly combined and remains light and fluffy.

Transfer the cheesecake mixture to a serving bowl or shallow dish and smooth the surface. Spoon the cherry pie filling over the top, leaving it in a distinct layer or swirling it lightly into the creamy base.

Serve immediately with graham crackers, vanilla wafers, pretzels, or fresh fruit. For a thicker, more cheesecake-like texture, cover and refrigerate the dip for approximately 30 minutes before serving.