12 Retro Pineapple Upside Down Cake Recipes

Ah, the pineapple upside-down cake— that glossy, caramelized gem from my childhood kitchen. I still remember the scent wafting through Grandma’s house in the 80s, her cast-iron skillet bubbling with buttery pineapple rings and maraschino cherries as she hummed along to the radio. It was the ultimate retro dessert, a symbol of effortless glamour that turned simple pantry staples into something magical. Those Sunday dinners weren’t complete without flipping that pan and revealing the jewel-toned masterpiece beneath.

Lately, I’ve been on a nostalgic kitchen binge, dusting off vintage cookbooks and experimenting with twists on this classic. In our fast-paced world of air fryers and meal kits, there’s something profoundly satisfying about reviving these mid-century recipes. They remind us of slower times, when baking was an art form that brought people together. Today, I’m sharing 12 retro-inspired variations to transport you back—each one easier than you think and packed with that signature gooey, fruity charm.

Classic 1950s Skillet Pineapple Upside Down Cake

This timeless version captures the essence of post-war Americana with its buttery brown sugar topping and juicy pineapple rings. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple slices (drained), 8-10 maraschino cherries, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter (softened), 2 eggs, 1 tsp vanilla, 1 1/2 tsp baking powder, 1/2 cup milk.
Melt 1/4 cup butter in a 10-inch cast-iron skillet, stir in brown sugar until dissolved, then arrange pineapple slices and cherries. Beat remaining ingredients into a batter and pour over fruit. Bake at 350°F for 30-35 minutes, then invert onto a plate.
It’s a crowd-pleaser with minimal effort, offering moist cake under caramelized fruit for under 400 calories per slice—perfect for retro potlucks.

Cherry-Glazed 1960s Pineapple Upside Down Cake

Elevate the original with a homemade cherry glaze for that mod-era shine. Ingredients: 1/4 cup butter, 2/3 cup brown sugar, 1 can pineapple chunks, 1/2 cup chopped cherries, 1 1/2 cups cake flour, 1 cup sugar, 1/2 cup oil, 3 eggs, 1 tsp almond extract, 1 tsp baking powder, 1/2 cup pineapple juice.
Caramelize butter and sugar in a round pan, add fruit. Mix batter and bake at 350°F for 35 minutes; cool and drizzle with cherry juice glaze (1/4 cup juice + 1 cup powdered sugar).
The glaze adds tangy brightness and antioxidants from cherries, making it a festive, digestion-friendly treat.

Coconut Dream 1970s Pineapple Upside Down Cake

Channel disco decadence with shredded coconut in both topping and batter. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple rings, 1 cup shredded coconut, 1 1/2 cups flour, 1 cup sugar, 1/2 cup coconut oil, 2 eggs, 1 tsp coconut extract, 1 1/2 tsp baking powder, 1/2 cup coconut milk.
Layer melted butter, sugar, pineapple, and half the coconut in a pan. Blend batter ingredients and bake at 325°F for 40 minutes; invert to reveal tropical layers.
Coconut boosts healthy fats for sustained energy, turning this into a vacation-in-a-bite dessert.

Rum-Infused 1940s Tiki Pineapple Upside Down Cake

A wartime favorite with a splash of rum for exotic flair. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple slices, cherries, 1/4 cup dark rum, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp vanilla, 1 tsp baking powder, 1/2 cup milk.
Simmer butter, sugar, and rum; top with fruit. Pour in batter and bake at 350°F for 30 minutes.
Rum adds depth and relaxation vibes, with pineapple aiding vitamin C intake.

Pecan-Crunch 1980s Pineapple Upside Down Cake

Big hair, big crunch—pecans elevate this to crunchy perfection. Ingredients: 1/4 cup butter, 2/3 cup brown sugar, 1 can pineapple, 1/2 cup chopped pecans, 1 1/2 cups flour, 1 cup sugar, 1/2 cup butter, 2 eggs, 1 tsp vanilla, 1 tsp baking soda, 1/2 cup buttermilk.
Toast pecans lightly, layer with butter-sugar-pineapple mix. Batter and bake at 350°F for 35 minutes.
Pecans provide omega-3s for heart health in this indulgent, nutty twist.

Banana-Boosted 1950s Pineapple Upside Down Cake

Mash in ripe bananas for extra moisture and Southern charm. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple rings, 2 mashed bananas, 1 1/2 cups flour, 3/4 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp banana extract, 1 tsp baking powder, 1/4 cup milk.
Arrange fruit in caramel base, mix banana batter, bake at 350°F for 32 minutes.
Bananas add potassium for muscle recovery—ideal post-workout nostalgia.

Spiced Ginger 1960s Pineapple Upside Down Cake

Warm spices nod to holiday retro vibes. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple, 1 tsp ground ginger, 1 1/2 cups flour, 1 cup sugar, 1/2 cup butter, 2 eggs, 1 tsp cinnamon, 1 tsp baking powder, 1/2 cup molasses-milk mix.
Infuse caramel with ginger, layer fruit, bake batter at 325°F for 38 minutes.
Ginger aids digestion, making this cozy cake gut-friendly.

Gluten-Free 1970s Pineapple Upside Down Cake

Retro fun for all, using almond flour. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple, cherries, 1 1/2 cups almond flour, 1/2 cup rice flour, 3/4 cup sugar, 1/3 cup coconut oil, 3 eggs, 1 tsp vanilla, 1 tsp baking powder.
Standard caramel top, gluten-free batter baked at 350°F for 30 minutes.
Gluten-free without sacrificing taste, plus almond protein boost.

Mini Bundt 1980s Pineapple Upside Down Cakes

Portion control with adorable bundts. Ingredients (for 12): 4 tbsp butter, 1/2 cup brown sugar, 1 can pineapple bits, cherries, 1 cup flour, 2/3 cup sugar, 1/4 cup butter, 1 egg, 1 tsp vanilla, 1 tsp baking powder, 1/3 cup milk.
Fill mini bundt pans halfway with caramel-fruit, top with batter, bake at 350°F for 20 minutes.
Fun singles mean no slicing fights, lower calories per serving.

Cream Cheese Swirl 1990s Pineapple Upside Down Cake

A creamy upgrade for the grunge era. Ingredients: Topping as classic; batter: 1 1/2 cups flour, 1 cup sugar, 1/2 cup butter, 2 eggs, vanilla; plus 8 oz cream cheese, 1/4 cup sugar, 1 egg.
Swirl cream cheese mix into batter before baking 35 minutes at 350°F.
Protein-rich cream cheese balances sweetness for satiety.

Hawaiian Macadamia 1960s Pineapple Upside Down Cake

Lei-inspired with nuts and coconut. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple, 1/2 cup macadamias + coconut, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp pineapple extract, baking powder, milk.
Layer tropical toppings, bake batter 35 minutes.
Macadamias offer healthy fats for a luau-worthy treat.

Chocolate-Drizzled 1950s Pineapple Upside Down Cake

Finish with retro chocolate ganache. Ingredients: Classic base; batter standard; ganache: 1/2 cup chocolate chips, 1/4 cup cream.
Bake as usual, drizzle cooled ganache.
Antioxidant chocolate elevates this to decadent delight.

These 12 retro pineapple upside-down cake recipes are your ticket to kitchen time travel—simple, forgiving, and guaranteed to wow. Grab a can of pineapple, preheat that oven, and whip one up this weekend. Your taste buds (and inner child) will thank you! Which will you try first? Share in the comments below.