In a small bowl, combine 2 cups chocolate sandwich cookie crumbs and melted butter.
Portion the crumbs into 28 2-ounce plastic cups using a small cookie scoop or spoon. Use one of the plastic cups to press the crumbs into the bottom of the cup.
In another mixing bowl, combine room temperature cream cheese and granulated sugar. Cream together with an electric hand mixer on medium speed until combined and smooth.
Add in heavy whipping cream and vanilla extract. Whip on medium-high speed until light and fluffy.
Fold in ½ cup chocolate sandwich cookie crumbs.
Fill a piping bag with the cookies and cream mixture. Pipe the mixture into the cups until about 3/4 full.
Top each dessert cup with a mini chocolate sandwich cookie or additional cookie crumbs.
Seal the cups with a lid and chill. The cups can be served immediately or stored in the refrigerator for 2-3 days.