Pineapple Upside-Down Pancakes

Pineapple Upside-Down Pancakes are the brunch showstopper that takes the retro American cake and rebuilds it, one golden round at a time, as a griddle dish worthy of any Sunday table. Each pancake is cooked directly over a caramelized pineapple ring — brown sugar and butter gurgling in the pan until deeply amber — then flipped to reveal a burnished, lacquered fruit crown. Stacked three high per plate, drizzled with the pan's caramel juices, they are simultaneously nostalgic and genuinely exciting.

The pineapple upside-down cake dates to the early 20th century in the United States, popularized with the commercial introduction of Dole canned pineapple rings in the 1920s. The original recipe appeared in the 1925 Dole recipe contest and has remained virtually unchanged for a century — its simplicity is its genius. The pancake adaptation retains the caramelized pineapple ring as the hero and brings the whole concept to a quicker, more brunch-appropriate format.

About the Pineapple

Fresh pineapple produces a markedly superior result to canned here — the rings can be cut to the exact thickness you want (¼ inch is ideal), and the natural sugars caramelize differently than the syrup in a can. Look for a pineapple that is fragrant at the base, golden-yellow in color, and yields slightly to pressure. The variety most widely available in American supermarkets is the Extra Sweet (MD-2), developed in Hawaii and now grown predominantly in Costa Rica and the Philippines. The Dole and Del Monte commercial varieties are both of this type (Del Monte Fresh Pineapple Guide).

Ingredients (serves 4, makes approximately 12 pancakes):

Caramelized Pineapple Base: - 1 medium fresh pineapple, peeled, cored, and sliced into ¼-inch rings (or one 20 oz can of pineapple rings, well drained) - 4 tablespoons unsalted butter - ½ cup packed light brown sugar - ¼ teaspoon ground cinnamon - Pinch of fine sea salt - 8–12 maraschino cherries (one per ring center, optional but traditional)

Buttermilk Pancake Batter: - 2 cups all-purpose flour - 2 tablespoons granulated sugar - 2 teaspoons baking powder - ½ teaspoon baking soda - ½ teaspoon fine sea salt - ½ teaspoon ground cinnamon - 2 large eggs - 1¾ cups full-fat buttermilk - ¼ cup whole milk - 3 tablespoons unsalted butter, melted and cooled - 1 teaspoon vanilla extract

To Serve: - Warm pure maple syrup or the reserved pineapple caramel pan juices - Whipped cream or crème fraîche - Fresh pineapple chunks for garnish

Caramel Pineapple Prep: In a wide non-stick or cast iron skillet over medium heat, melt butter and add brown sugar, cinnamon, and salt. Stir until the butter and sugar melt together into a smooth, bubbling caramel — about 2 minutes. Place pineapple rings in the caramel and cook 2–3 minutes per side until deeply golden and caramelized. Remove rings to a plate; reserve the pan caramel. If using maraschino cherries, press one into the center of each ring now.

Batter: Whisk flour, sugar, baking powder, baking soda, salt, and cinnamon in a large bowl. In a separate bowl, whisk eggs, buttermilk, milk, melted butter, and vanilla. Pour wet into dry and stir until just combined — lumps are fine and expected. Do not overmix; overmixed pancake batter develops gluten and produces tough, dense pancakes.

Cooking: Heat a griddle or wide non-stick skillet over medium heat. Brush lightly with butter. Place a caramelized pineapple ring in the center of the cooking area. Immediately pour approximately ⅓ cup of batter directly over and around the pineapple ring so it fills the inside of the ring and spreads slightly beyond. Cook until bubbles form across the surface and the edges look set — about 3 minutes. Flip in one confident motion and cook 1½–2 minutes more. The pineapple side should be deeply golden.

Transfer to a warm plate and keep in a 200°F oven while you complete the batch.

Assembly: Stack three pancakes per person, pineapple side up. Drizzle the reserved pan caramel generously over the stack. Add a cloud of whipped cream alongside. Serve warm maple syrup separately.

The Pairing: Pineapple Upside-Down Pancakes alongside a Tropical Mango Mimosa or a classic Champagne Brut creates one of the finest brunch pairings — the sparkling wine's acidity cuts through the caramel and complements the tropical sweetness of the pineapple.

Variations: - Pineapple Coconut Pancakes: Replace ½ cup of the buttermilk with full-fat coconut milk and fold ½ cup toasted shredded coconut into the batter - Spiced Rum Caramel Version: Add 1 tablespoon of dark rum to the caramel at the end of cooking for a boozy, adult-oriented depth - Hawaiian Version: Add a slice of Spam lightly pan-fried alongside for the full Hawaiian experience (genuinely excellent)

Reference Links: - Pineapple selection guide: Del Monte Fresh - Original pineapple upside-down cake history: Smithsonian Magazine - Buttermilk pancake technique: Serious Eats

Pro Tips: The caramelized pineapple rings must be cooked separately before the pancakes — attempting to caramelize in the pan with raw batter poured over produces uneven caramelization and steaming rather than browning. The batter should rest for 5 minutes after mixing: this allows the baking powder to activate and produces a lighter, more aerated pancake. Work quickly when placing the ring in the pan and pouring the batter — the caramel in the ring should still be warm and sticky when the batter goes in.