01 - In a small saucepan over medium heat, melt 2 tablespoons of unsalted butter. Stir in the light brown sugar until fully dissolved and a smooth caramel mixture forms. Remove from heat.
02 - Preheat a large nonstick skillet or griddle over medium heat. Lightly grease the cooking surface with butter or a nonstick cooking spray.
03 - Spoon a portion of the prepared brown sugar mixture onto the preheated skillet for each pancake. Place one drained pineapple ring onto the sugar mixture and position a drained maraschino cherry in the center of each pineapple ring.
04 - In a large mixing bowl, whisk together the all-purpose flour, granulated sugar, baking powder, baking soda, and salt until thoroughly combined.
05 - In a separate bowl, whisk together the whole milk, large eggs, melted unsalted butter, and pure vanilla extract until smooth.
06 - Pour the wet ingredients into the bowl with the dry ingredients. Mix gently until just combined. Be careful not to overmix; a few small lumps are acceptable.
07 - Pour approximately 1/3 cup of pancake batter over each prepared pineapple ring, gently spreading to ensure the batter covers the ring and forms a pancake shape. Cook for 2-3 minutes, or until bubbles appear on the surface and the edges begin to set. Carefully flip the pancakes with a spatula and cook for an additional 2 minutes, until golden brown and cooked through.
08 - Serve the pancakes warm, with the pineapple side facing upwards. Repeat the cooking process with the remaining batter and ingredients, re-greasing the skillet as necessary.