Preheat your oven to 350°F. Grab a 9-inch round cake pan. Trust me, nonstick makes life easier here.
Melt the 1/4 cup butter in the pan over low heat, then sprinkle in the brown sugar and stir until it's kind of bubbly and syrupy.
Lay your pineapple slices right into that sticky heaven. Tuck a cherry in the middle of each slice. You’re creating edible artwork.
In a big bowl, beat together the flour, sugar, softened butter, baking powder, salt, milk, egg, and vanilla until smooth.
Pour that luscious batter over your pineapple layer—carefully now. Don’t dislodge your masterpiece.
Bake for 30-35 minutes, or until a toothpick comes out clean. The top should be golden and your kitchen will smell unreal.
Let it cool for 5 minutes (just enough time to build some suspense), then run a knife around the edges and flip it onto a serving plate. Flip fast and steady—no hesitation!
Let it sit a minute. Then lift the pan. Drumroll, please… ta-da! Serve warm. Maybe with ice cream. Definitely with pride.