Preheat oven to 350 degrees. Spray a 9 by 2-inch cake pan with non-stick cooking spray.
In a mixing bowl whisk together brown sugar and 1/4 cup melted butter then pour into prepared cake pan and spread into an even layer, set aside.
Spread pineapple chunks over brown sugar layer in rows (leave about 1/4-inch between pieces for cake batter to fill in). Set aside.
In a mixing bowl whisk together flour, baking powder, and salt, set aside.
In the bowl of an electric stand mixer (or in a mixing bowl using an electric hand mixer) whip together granulated sugar and 1/2 cup softened butter until pale and fluffy.
Add in one egg and mix until combined, then mix in second egg and vanilla.
Add 1/3 of the flour mixture and mix just until combined, then mix in 1/3 cup milk blending just until combined. Mix in another 1/3 cup flour then mix in remaining 1/3 cup milk. Mix in last 1/3 cup flour.
Pour and spread batter evenly over pineapple layer. Bake in preheated oven until toothpick inserted into center comes out clean, about 35 - 40 minutes.
Remove and let cool on wire rack 10 minutes. Run an offset spatula or knife around edges to ensure it's loosened then invert onto a serving platter.
If topping with whipped cream let cool completely. Garnish with cherries if desired.
Whipped cream and cherries not including in nutritional information.
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