Grease a large bundt pan generously with butter or nonstick spray.
In a small bowl, mix the melted butter and brown sugar.
Pour this mixture evenly into the bottom of the prepared bundt pan.
Arrange pineapple slices on top of the brown sugar mixture. Set aside.
2. Make the Pound Cake Batter:
In a large bowl, cream together the softened butter, cream cheese, and sugar until light and fluffy (about 3–5 minutes).
Add the eggs one at a time, beating well after each addition.
Mix in the vanilla extract and crushed pineapple.
In a separate bowl, whisk together the flour, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture, mixing just until combined. Do not overmix.
3. Bake the Cake:
Pour the batter evenly over the pineapple topping in the bundt pan.
Tap the pan lightly on the counter to release air bubbles and smooth the top with a spatula.
Bake for 75–90 minutes, or until a toothpick inserted in the center comes out clean. Check at the 75-minute mark and tent with foil if browning too quickly.
4. Cool & Flip:
Allow the cake to cool in the pan for 10–15 minutes before inverting onto a serving plate.
Let it cool completely before slicing. This allows the topping to set and the flavors to deepen.