Spray two large silicone muffin tins with nonstick spray. In a large bowl, combine the vanilla wafer crumbs with the melted butter and 2 tablespoons sugar until evenly incorporated. Divide the mixture evenly into two large silicone muffin trays. Press down evenly to form a smooth even crust. Place the pans in the freezer.
In a medium bowl, whisk together the pudding mix, milk and bourbon until well combined. Place in the fridge and let chill until firm.
In the bowl of a stand mixer fitted with the paddle attachment, beat the cream cheese and sugar until light and fluffy, about 2 minutes. Add the chilled pudding and mix until just combined. Fold in 2 cups Cool Whip, being careful not to over-mix.
Divide evenly into the muffin pans over the crust and spread to make smooth. Place in the refrigerator and chill for at least 4 hours or overnight. Place in freezer for an hour before serving.
Remove the chilled cheesecakes from the pans and place on a plate or platter. Place 2 cups cool whip in a piping bag fitted with a medium star tip. Dollop each cheesecake with a bit of Cool Whip and spread out into an even layer. Place a whole vanilla wafer in the center of each cheesecake then pipe a decorative border around the edge of each cheesecake.