In a medium mixing bowl, combine the graham cracker crumbs and the 1 stick of melted unsalted butter. Stir firmly with a spoon or fork until the crumbs are completely moistened and resemble wet sand.

Set aside exactly ¼ cup of the buttered crumbs to use later as a topping. Dump the remaining crumbs into a 9×13-inch baking dish and use the flat bottom of a measuring cup or glass to firmly compress the mixture into a flat, tight, and even crust layer. Slide the dish into the refrigerator to chill while preparing the filling.

In a large mixing bowl, combine the room-temperature cream cheese and the remaining 1 stick of room-temperature unsalted butter. Beat with an electric hand mixer on medium-high speed for 2 to 3 minutes until the mixture turns pale, light, and completely smooth without any lumps.

Reduce the mixer speed to low and slowly add the sifted powdered sugar in batches, mixing continuously until fully incorporated. Once the sugar is in, increase the speed to high and beat for another 1 to 2 minutes until the filling is light and fluffy.

Empty the can of crushed pineapple into a fine-mesh strainer. Use the back of a large spoon or a spatula to firmly press the fruit against the mesh to squeeze out as much excess juice as possible. Eliminating this pooling liquid is essential to prevent the cream layers from turning runny.

Gently fold the drained crushed pineapple and the whipped topping straight into the sweetened cream cheese mixture using a silicone spatula. Stir slowly from the bottom up just until the elements are unified to avoid deflating the aerated whipped texture.

Remove the chilled crust from the refrigerator. Spoon the pineapple cream mixture evenly over the top, using an offset spatula to smooth the surface into a flat, level sheet.

Scatter the reserved ¼ cup of graham cracker crumbs uniformly across the top of the dessert. If desired, arrange the sliced maraschino cherries on top to create a vibrant visual contrast.

Cover the dish tightly with plastic wrap and transfer to the refrigerator to chill for at least 4 hours, or ideally overnight. This extended cooling window allows the fats to solidify and the starches to lock together, ensuring clean, beautiful squares when sliced and served.