Line an 8x4-inch loaf pan with plastic wrap, allowing the wrap to hang over the sides completely.

Place cream in a large bowl and beat with an electric mixer on medium speed for 2 minutes. Add powdered sugar and vanilla extract; continue to beat until soft-medium peaks form. Reserve 1 cup of whipped cream and refrigerate until ready to use.

Place a thin layer of whipped cream in the bottom of the prepared pan. Reserve 2 cookies for garnish. Add a layer of cookies over the cream, breaking any cookies as necessary to fill in any empty spaces; top with 1/4 of remaining cream. Top with another layer of cookies and another 1/4 of remaining cream. Repeat the process two more times until all the cream is used. Top with remaining cookies, pressing them into the cream.

Wrap the plastic around the loaf and refrigerate at least 8 hours.

Unwrap cake and invert onto a serving plate. Top cake with reserved whipped cream. Crush reserved 2 cookies and sprinkle on top as garnish; slice and serve as desired.