Mix crushed cookies and melted butter. Press into the bottom of an 8x8-inch or 9x9-inch pan.
Stir together pudding mix, pineapple, and half the cool whip container. Spread evenly over crust.
Top with remaining cool whip and more crushed cookies, if desired. Chill at least 2 hours before serving.
Store in refrigerator covered for up to 3 days.