In a medium bowl, mix crushed graham crackers, granulated sugar, and melted unsalted butter until evenly coated. Set aside.

In a large bowl, beat softened cream cheese with an electric mixer on medium speed until smooth. Gradually add sweetened condensed milk, lemon juice, and vanilla, mixing until fluffy.

Layer 2 tablespoons of graham cracker mixture into the bottom of each clear cup, pressing down lightly to form an even base.

Add 3 tablespoons of the cheesecake filling on top of the crust, smoothing it out.

Spoon half of the cherry pie filling evenly over the cheesecake layer in each cup.

Repeat with another layer of graham cracker mixture and top with the remaining cheesecake filling, smoothing it down.

Divide the remaining cherry pie filling on top and sprinkle some reserved graham cracker crumbs if desired.

Enjoy immediately or refrigerate for up to 24 hours before serving.