Place 19 cookies (filling and all) into a food processor fitted with the steel blade. Process until ground into fine crumbs. Add the melted butter and pulse several times to combine. Dump the mixture into a 9-inch, deep-dish pie pan and press firmly and evenly on the bottom and up the sides of the pan. Freeze for 15 minutes.

Spread the softened ice cream into the frozen pie crust and smooth the top. Freeze for at least 4 hours or up to 2 days.

Coarsely crush the remaining 3 cookies. Spread the whipped cream over the ice cream layer, sprinkle the crushed cookies on top, and drizzle with some caramel syrup.

Serve immediately or store in the freezer until ready to eat.