Prepare the Crust: In a small bowl, mix together the crushed graham crackers, brown sugar, and melted butter until well combined. Press the mixture into the bottoms of shot glasses or small dessert cups to form the crust.
Make the Cheesecake Filling: In a large bowl, beat the softened cream cheese and powdered sugar until smooth and creamy. Add the Fireball Whiskey and vanilla extract, beating until fully incorporated. Gently fold in the whipped cream until the mixture is light and fluffy.
Assemble the Shots: Pipe or spoon the cheesecake filling over the graham cracker crust in each shot glass. Smooth the tops with a spatula.
Add the Toppings: Top each shot with a dollop of whipped cream, a maraschino cherry, and a drizzle of caramel sauce if desired.
Chill and Serve: Refrigerate the shots for at least 1 hour before serving to allow the flavors to meld.