Coffee Whipped Cream:
1. Combine ½ cup coffee grounds and 1 cup heavy cream in a small saucepan and stir over low heat for 6-10 minutes. Let chill completely in refrigerator.
2. Strain the cream, using cheesecloth or a super-fine mesh sieve, and discard the grounds. Add the powdered sugar to the cream, whip until soft peaks form, and refrigerate until needed.
Chocolate-Coffee Crust:
1. Preheat oven to 375 degrees Fahrenheit.
2. In a medium bowl, combine crushed cookies, remaining ¼ cup coffee grounds, and melted butter. Press into a pie plate with a measuring cup to form an even crust.
3. Bake crust for 10 minutes. Set aside to cool.
French Silk Pie Filling:
1. Melt chocolate in a microwave at 15 second increments, stirring often. Set aside.
2. Cream butter and sugar in a stand mixer until light and fluffy, about 3 minutes. Add cooled chocolate and vanilla and mix until combined.
3. Add eggs one at a time, beating mixture for 5 minutes between each egg.
4. Whip ½ cup heavy cream in a separate bowl until soft peaks form, then fold into filling.
5. Spread filling evenly into crust and top with coffee whipped cream. Refrigerate to set, at least 2 hours or overnight.