Preheat oven to 350 degrees. Pulse chocolate cookies in food processor until they turn into crumbs. Place crumbs in a medium bowl. Add melted butter and stir together with a fork.
Grease cups of mini cheesecake pan. Spoon 1 tablespoon of cookie crumbs into each cup. Using the bottom of a shot glass, pack down the crumbs to make a cookie crust.
Cut all regular peanut butter cups into quarters. Place one quarter peanut butter cup over cookie crust of each cheesecake cup. Repeat with rest of quarters. Set aside.
Add sugar and cream cheese to the bowl of a stand mixer. Beat on medium for 3 minutes. Add peanut butter cup and beat until combined and creamy. Add eggs, beating one at a time. Add vanilla and mix until combined. Fold in crushed Butterfingers
Scoop 1 1/2 tablespoons of cheesecake batter into each cheesecake cup, leaving about 1/4 inch free from the top. Smack down pans to release air bubbles from the cheesecake cups.
Bake in preheated oven for 15 minutes or until edges are firm but center is still jiggly. Remove from oven and let cool in pan for 15 minutes before placing in refrigerator to set and cool completely for 3-4 hours, while still keeping in the pan.
Once cheesecakes have set, prepare the whipped cream. Add heavy cream to a bowl of a stand mixer with sugar. Whip on medium-high until very stiff peaks form. Add whipped cream to a piping bag fitted with a star tip.
Remove cheesecakes from the pan by pushing up cheesecakes from the bottom. Pipe little peaks on top of each cheesecake and sprinkle with more crushed Butterfingers. Top centers of whipped cream with a slice of a peanut butter cup.