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Preheat the oven to 325°F and spray a 9-inch springform pan with cooking spray.
Place Oreo cookies in a food processor (or smash them in a sealed bag) to make fine crumbs.
Pour melted butter slowly into the food processor and pulse until the crust comes together. (Alternatively, stir together in a mixing bowl until evenly moistened.) Press the crumbs into the bottom and up the sides of your springform pan. Bake for 8 minutes, then remove from the oven. Leave the oven on.
Add cream cheese, sugar, and vanilla to a mixing bowl and blend on medium speed until smooth. Add eggs one at a time, beating just until blended.
Pour the batter into the prepared crust. Bake for 25-30 minutes or until set. Remove from the oven and let it cool completely.
Place heavy cream, sugar, and vanilla in a bowl and blend on medium speed until stiff peaks form, then gently fold in the crushed pineapple
Spread the mixture over the cooled cream cheese layer.
Refrigerate for at least 6 hours (overnight is best).
For the topping, preheat the oven to 350°F and line a small baking sheet with parchment paper.
Spread coconut flakes over the parchment paper and bake for about 5 minutes, or until golden brown around the edges.
Have fresh pineapple chunks ready to arrange on top of cheesecake slices, and sprinkle with toasted coconut.