Preheat oven to 350° Fahrenheit. Lightly grease 9x13 baking dish with butter or neutral-flavored cooking spray and set aside.
Add ½ cup salted butter and 1 cup granulated white sugar to large mixing bowl (or stand mixer bowl). Use hand mixer (or stand mixer) fitted with paddle or flex edge attachment to beat butter and sugar together on medium speed until mixture is fluffy and pale yellow, approximately 2 to 5 minutes.
After creaming butter and sugar, crack 4 large eggs directly into mixing bowl, one by one, making sure egg is fully incorporated into butter-sugar mixture before adding next egg.
Once all 4 eggs have been fully incorporated into butter-sugar mixture, add 1 20-ounce can crushed pineapple to bowl. Stir pineapple into butter-sugar mixture by hand until fully incorporated.
Once pineapple is fully incorporated, add cubes of 10 slices soft white bread to bowl. Gently fold bread cubes into pineapple mixture until just incorporated.
Transfer pineapple mixture to prepared baking dish, spreading mixture evenly across dish, then place filled baking dish in preheated oven.
Bake pineapple stuffing 45 minutes. After 45 minutes, or when top of stuffing begins to brown, carefully remove baking dish from oven and cover dish with aluminum foil.
Return baking dish to oven and bake, covered, 15 minutes. Once stuffing is bubbly and golden, carefully remove baking dish from oven.
Uncover dish and let stuffing stand 3 to 5 minutes or until slightly firm. Serve warm.