Prepare the Pan: Grease a round cake pan and line the bottom with parchment paper. Arrange pineapple slices and maraschino cherries in a decorative pattern on the bottom of the pan.
Make the Cake Batter: In a bowl, cream together butter and brown sugar until light and fluffy. Add eggs, vanilla extract, and pineapple juice, mixing until well combined.
Pour Batter Over Pineapple: Carefully pour the cake batter over the arranged pineapple slices in the prepared pan, spreading it evenly with a spatula.
Bake Until Golden: Bake the cake in a preheated oven until golden brown and a toothpick inserted into the center comes out clean.
Cooling and Inverting: Allow the cake to cool in the pan for about 10 minutes. Then, place a serving plate upside down over the pan and carefully invert the cake onto the plate.
Serve and Enjoy: Slice the Pineapple Upside Down Cake and serve it warm or at room temperature.