12 Retro Pineapple Upside Down Cake Recipes

Ah, the pineapple upside-down cake—nothing transports me back to my grandmother’s kitchen quite like it. I can still picture her on lazy Sunday afternoons, carefully arranging glistening pineapple rings and maraschino cherries in a cast-iron skillet, the buttery brown sugar bubbling up like liquid gold. The aroma of caramelizing fruit and vanilla batter baking would waft through the house, drawing us all to the table for a slice of pure nostalgia. That first flip onto the plate, revealing the golden, jewel-like top, was pure magic and my first lesson in the joy of retro baking.

Lately, I’ve been on a mission in my own kitchen to revive these vintage gems, experimenting with twists from old church cookbooks I scored at a flea market. In our fast-paced world of air fryers and no-bake trends, there’s something deeply satisfying about these hands-on, from-scratch delights. They’re not just desserts; they’re a warm hug from the past, perfect for potlucks, family dinners, or just a cozy night in.

Classic 1950s Pineapple Upside Down Cake

This timeless version sticks to the mid-century script: buttery brown sugar topping with pineapple rings and cherries, baked into a tender yellow cake. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple slices (drained), 8-10 maraschino cherries, 1 1/2 cups cake flour, 1 cup sugar, 1/2 cup butter (softened), 2 eggs, 1 tsp vanilla, 1 tsp baking powder, 1/2 cup milk. Melt butter and brown sugar in a 9-inch skillet, arrange pineapple and cherries, then mix batter and pour over. Bake at 350°F for 35-40 minutes until golden; invert to serve. It’s moist, caramelized perfection with zero fuss—ideal for beginners craving authentic retro flavor.

The benefits? Incredibly nostalgic, naturally gluten-structured for fluffiness, and a crowd-pleaser that uses pantry staples for under $10.

Cherry-Filled Vintage Pineapple Upside Down Cake

Elevate the original with extra cherries tucked into the batter for bursts of tart-sweet joy. Ingredients: Same as classic, plus 1/2 cup chopped maraschino cherries and 1/4 tsp almond extract. Prepare skillet topping as usual, fold cherries into batter, bake 40 minutes at 350°F, and flip. Simple assembly yields a festive, fruit-packed cake that’s still ready in under an hour.

Health perk: Antioxidants from cherries boost it beyond dessert, while the moist crumb keeps it guilt-free indulgent.

Rum-Soaked 1960s Pineapple Upside Down Cake

A boozy nod to tiki-era parties, infused with dark rum for depth. Ingredients: Classic base, substitute 1/4 cup rum for half the milk, plus 2 tbsp rum in topping. Simmer brown sugar, butter, and rum for topping; add pineapple/cherries, batter over, bake 38 minutes at 350°F. Brush extra rum post-bake for soak.

Benefits: Adulthood upgrade adds sophisticated warmth; rum tenderizes for extra moistness without sogginess.

Coconut-Crusted Tropical Pineapple Upside Down Cake

Channel Hawaiian shirts with toasted coconut in the topping and batter. Ingredients: Classic, plus 1 cup shredded coconut (1/2 in topping, 1/2 in batter), 1/2 tsp coconut extract. Mix coconut into brown sugar melt, layer fruit, fold into batter, bake 40 minutes at 350°F.

Perks: Texture contrast from crunchy coconut, tropical vibe makes it vacation-in-a-bite, naturally dairy-optional.

Skillet-Fried Grandma’s Pineapple Upside Down Cake

Old-school cast-iron method for crispy edges. Ingredients: Classic list. Melt topping directly in 10-inch skillet on stovetop, add fruit, pour batter, transfer to 350°F oven for 35 minutes—no mixing bowl needed.

Advantages: One-pan wonder minimizes cleanup, skillet retains heat for perfect caramelization and diner-style appeal.

Spiced Autumn Pineapple Upside Down Cake

Retro fall twist with cinnamon and nutmeg. Ingredients: Classic, add 1 tsp cinnamon, 1/2 tsp nutmeg to batter, sprinkle cinnamon on topping. Layer as usual, bake 37 minutes at 350°F.

Benefits: Warm spices enhance fruit flavors, comforting for cooler days, antioxidant spices add subtle wellness.

Mango-Infused 1970s Pineapple Upside Down Cake

Fusion retro with fresh mango alongside pineapple. Ingredients: Half pineapple/half mango slices, classic base + lime zest. Arrange fruits in topping, batter over, bake 40 minutes.

Perks: Brighter, vitamin-C-packed fruit duo, keeps it light and modern-retro hybrid.

Gluten-Free Retro Pineapple Upside Down Cake

Almond flour swap for inclusive nostalgia. Ingredients: 1 1/2 cups almond flour, 1/2 cup rice flour, rest classic (use dairy-free butter). Topping same, batter mixes quick, bake 35 minutes at 350°F.

Benefits: Nutty flavor elevates taste, celiac-friendly without sacrificing tenderness.

Vegan Delight Pineapple Upside Down Cake

Plant-based take using aquafaba and coconut oil. Ingredients: 1/4 cup coconut oil + brown sugar for topping, aquafaba (from 1 can chickpeas) whipped for eggs, oat milk, classic drys. Assemble and bake 40 minutes.

Advantages: Egg-free rise is spot-on, fully vegan for all diets, equally decadent.

Mini Bundt Pineapple Upside Down Cakes

Portion-perfect for parties, retro charm in bites. Ingredients: Classic batter scaled for 12 bundts; mini pineapple bits/cherries in each. Fill greased pans, bake 20 minutes at 350°F, invert individually.

Perks: Freezer-friendly, elegant presentation, portion control for guiltless seconds.

Pecan-Crunch Pineapple Upside Down Cake

Southern retro with nuts for crunch. Ingredients: Classic + 1/2 cup chopped pecans in topping and batter. Scatter pecans under fruit, bake 38 minutes.

Benefits: Protein from pecans balances sweetness, toasty nuts add luxury texture.

Chocolate-Drizzled Midnight Pineapple Upside Down Cake

Decadent 80s twist with chocolate cake base. Ingredients: Swap yellow batter for chocolate (add 1/3 cup cocoa), classic topping, drizzle melted chocolate post-flip. Bake 40 minutes.

Perks: Fruit-chocolate harmony surprises, indulgent yet fruity for balance.

There you have it—12 ways to flip nostalgia onto your plate! Dust off that skillet, gather your loved ones, and try these retro pineapple upside-down cakes this weekend. Which one will be your new favorite? Share your bakes in the comments—I can’t wait to hear!