Preheat the oven to 350 degrees Fahrenheit and lightly spray a 9 x 13 x 2.5-inch baking pan with nonstick cooking spray and set aside.
Crust
Combine 2 ¾ cups graham cracker crumbs, 3 tablespoons granualted sugar, and ¾ cup melted salted butter in a medium bowl until the mixture resembles damp sand.
Press the crumb mixture evenly into the bottom of the pan using a flat-bottomed glass or measuring cup. Bake for 10-12 minutes, until fragrant and the edges are golden brown.
Remove the crust from the oven and allow it to cool completely before topping it with the subsequent layers.
Cheesecake Layer
Add 2 (8-ounce) packages softened cream cheese and ½ cup softened salted butter to a large bowl and beat on medium-high speed with a hand mixer or stand mixer fitted with the paddle attachment until smooth. Scrape down the sides and bottom of the bowl as needed to ensure no lumps remain.
Add 2 ½ cups powdered sugar and 1 tablespoon vanilla extract and beat on low until the sugar is mostly incorporated, then increase the speed to medium-high until smooth and creamy.
Spread the cheesecake mixture evenly over the cooled crust.
Pineapple Topping
Carefully fold 2 (20-ounce) drained cans crushed pineapple into 2 (8-ounce) containers thawed whipped topping before spreading the whipped mixture evenly over the top of the cheesecake layer.
Cover and refrigerate for at least 4 hours. Top with graham cracker crumbs and pineapple tidbits before serving.
Notes
Storing: Store pineapple delight in the fridge, covered, for up to 5 days. For longer storage, wrap it well and freeze for up to 3 months. Thaw overnight or enjoy it frozen!