Add the graham cracker crumbs to a small bowl along with the melted butter. Stir well to combine.
Press the crumb mixture into the bottom of an 8x8 cake pan or baking dish. Allow to chill in the fridge for at least 30 minutes to set up.
Using either a stand mixer or a handheld mixer, cream together the softened butter, cream cheese, and vanilla. Carefully add the powdered sugar a ½ cup at a time. Mix until the cream cheese mixture is smooth.
Evenly spread the cream cheese filling over the completely cooled crust.
In a clean bowl, add the heavy cream and ¼ cup of sugar. Beat on medium-high speed for about 2 minutes until stiff peaks begin to form.
Gently fold the pineapple into the whipped cream. Spread the cream mixture over the cream cheese layer.
Add the additional 1 tablespoon of crushed graham crackers to the top as garnish.
Place the baking dish in the refrigerator for 4 hours to ensure the dessert is properly set.
Keep refrigerated until serving. Serve with a dollop of whipped cream and a wedge of pineapple for decoration (optional)