Prepare the base: In a bowl, mix the crushed cookies with the melted butter until moist. Line the bottom of a springform pan with this mixture, pressing firmly to compact. Refrigerate for 15 minutes to firm up.
Prepare the filling: In a bowl, beat the cream cheese with the granulated sugar and vanilla extract until smooth and creamy. Add the crushed and drained pineapple, beating until well blended. Add the whipped cream:
In a separate bowl, beat the whipped cream with the icing sugar until soft peaks form. Gently fold it into the cream cheese and pineapple mixture, stirring until smooth and creamy.