Set out cream cheese and butter to soften. (Aloha Tip: to use immediately, you can soften the cream cheese by completely unwrapping it, placing in a microwave safe bowl and microwaving it for 10 seconds. You can do the same with the butter).

Set out cream cheese and butter to soften. (Aloha Tip: to use immediately, you can soften the cream cheese by completely unwrapping it, placing in a microwave safe bowl and microwaving it for 10 seconds. You can do the same with the butter.)

Put complete Oreo cookie (both cookie and filling) in the food processor and blend using pluses until they are the texture of sand. Set aside.

In a medium bowl combine cream cheese, butter, and powdered sugar with mixer. Fold in Cool Whip until well combined. In a separate bowl mix pudding mix and milk with a whisk. When well combined, add pudding to cream cheese mixture. Spoon the pudding cream cheese mixture into a 1 gallon bag. Place bag in a bowl and refrigerate for 15 minutes to get thicker.

Drain the pineapple in a strainer for 10 minutes, pressing down to remove the extra juice).

MAKE AHEAD NOTE: Can be made to this point up to 1 day ahead. Cover the Oreo crumbs and refrigerate the pineapple and cream cheese mixtures each in a separate covered container.

To assemble, place several tablespoons of Oreo crumbs in each tumbler. Cut off the corner of the baggie containing the pudding mixture. Add about ½ inch of the cream cheese pudding mixture to each tumbler. Gently tap the tumblers on the counter to displace any air bubbles if necessary. Add a thin layer of the crushed pineapple. Add another thin layer of Oreo Crumbs. Add a second thin layer of the pudding mixture followed with a second thin layer of the crushed pineapple. Top off with a sprinkling of the Oreo crumbs and a drink umbrella.

Refrigerate until ready to serve.  Best made the same day, but can be made the night before.