12 Retro Pineapple Upside Down Cake Recipes

Ah, the irresistible allure of pineapple upside-down cake—those glossy rings of caramelized pineapple and bright red maraschino cherries peeking through a golden cake top that flips to reveal pure nostalgia. I still remember being a kid in my grandma’s kitchen in the 1970s, perched on a stool watching her carefully arrange canned pineapple slices in a cast-iron skillet, the buttery brown sugar bubbling like magic. The house would fill with that sweet, tropical scent, and we’d devour warm slices with vanilla ice cream, creating memories sweeter than the glaze itself.

Lately, I’ve been on a retro recipe kick, digging through my collection of vintage church cookbooks and mid-century magazines to revive this iconic dessert. In our fast-paced world of air fryers and meal kits, there’s something profoundly comforting about these simple, no-fuss cakes that rely on pantry staples. They’re not just desserts; they’re a ticket back to simpler times, perfect for potlucks, family dinners, or just a midweek treat that screams “homemade love.”

Classic Maraschino Cherry Pineapple Upside-Down Cake

This timeless version captures the essence of 1950s diner desserts with its buttery brown sugar topping and juicy pineapple rings studded with cherries. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple slices (drained, reserve juice), 8-10 maraschino cherries, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter (softened), 2 eggs, 1 tsp vanilla, 2 tsp baking powder, 1/2 tsp salt, 1/2 cup pineapple juice + milk to make 1 cup.
Melt butter in a 9-inch skillet, stir in brown sugar until bubbly, arrange pineapple and cherries. Mix batter ingredients, pour over fruit, bake at 350°F for 35-40 minutes, invert onto plate. Benefits include its crowd-pleasing simplicity, moist crumb, and natural sweetness that cuts sugar needs—gluten-full but nostalgic perfection.

Coconut Crusted Hawaiian Pineapple Upside-Down Cake

Evoking 1960s luau vibes, this adds shredded coconut for a tropical crunch. Ingredients: 1/4 cup butter, 2/3 cup brown sugar, 1 can pineapple slices, maraschino cherries, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp vanilla, 2 tsp baking powder, 1/2 tsp salt, 1/2 cup coconut milk, 1/2 cup shredded coconut (toasted for topping).
Prepare skillet with butter, sugar, pineapple, and cherries; sprinkle coconut around edges. Beat batter with coconut milk, pour over, bake 350°F for 40 minutes, flip. Benefits: Enhanced flavor with healthy fats from coconut, adds texture, and it’s dairy-adaptable for richer indulgence.

Pecan Praline Pineapple Upside-Down Cake

A Southern twist from 1970s cookbooks, pecans caramelize into praline bliss. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple slices, cherries, 1 cup chopped pecans, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp vanilla, 2 tsp baking powder, 1/2 tsp salt, 3/4 cup milk.
Layer butter, sugar, pecans, pineapple, and cherries in skillet. Mix and pour batter, bake 350°F 35-40 minutes, invert. Benefits: Protein boost from nuts, nutty depth reduces sweetness overload, perfect for nut lovers seeking retro crunch.

Rum-Soaked Tropical Pineapple Upside-Down Cake

Inspired by 1940s tiki bars, a splash of rum elevates the glaze. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 2 tbsp dark rum, 1 can pineapple, cherries, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp vanilla, 2 tsp baking powder, 1/2 tsp salt, 3/4 cup milk.
Melt butter with sugar and rum, add fruit. Batter as usual, bake 350°F 40 minutes, drizzle extra rum post-flip. Benefits: Adult sophistication with minimal alcohol, tenderizes cake, and antioxidants from pineapple pair with rum’s warmth.

Banana Foster Pineapple Upside-Down Cake

Merging 1950s New Orleans flair, bananas add creamy layers. Ingredients: 1/4 cup butter, 2/3 cup brown sugar, 1 can pineapple slices, 2 bananas (sliced), cherries, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp vanilla + cinnamon, 2 tsp baking powder, 1/2 tsp salt, 3/4 cup milk.
Arrange bananas with pineapple in butter-sugar base. Bake batter 350°F 40 minutes, flip. Benefits: Potassium-rich bananas for heart health, doubles fruitiness for natural sweetness, moist and exotic.

Spiced Ginger Pineapple Upside-Down Cake

Retro holiday spice from old Betty Crocker pages. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple, cherries, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp vanilla + 1 tsp ginger + 1/2 tsp cinnamon, 2 tsp baking powder, 1/2 tsp salt, 3/4 cup milk.
Layer fruit in spiced butter-sugar mix. Add spices to batter, bake 350°F 35 minutes, invert. Benefits: Anti-inflammatory ginger aids digestion, warms the soul, seasonal twist on classic.

Almond Amaretto Pineapple Upside-Down Cake

1960s cocktail party elegance with nutty liqueur. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 tbsp amaretto, 1 can pineapple, cherries, 1/2 cup sliced almonds, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp almond extract, 2 tsp baking powder, 1/2 tsp salt, 3/4 cup milk.
Toast almonds lightly, layer with fruit in booze-infused base. Batter with extract, bake 350°F 40 minutes. Benefits: Almonds for vitamin E skin glow, sophisticated flavor without overpowering.

Vintage Cast Iron Skillet Pineapple Upside-Down Cake

Pure 1940s farmhouse style, baked in the skillet. Ingredients: 1/4 cup butter, 2/3 cup brown sugar, 1 can pineapple, cherries, 1 1/2 cups flour, 3/4 cup sugar, 1/3 cup shortening, 1 egg, 1 tsp vanilla, 2 tsp baking powder, 1/2 tsp salt, 1/2 cup milk.
Heavy skillet method: melt base, add fruit, pour thin batter, bake 350°F 30-35 minutes, serve from pan. Benefits: Even heat for perfect caramel, one-pan ease, hearty retro texture.

Mini Pineapple Upside-Down Cake Bites

1970s party appetizers, bite-sized for sharing. Ingredients (for 24): 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple tidbits, cherries (quartered), 1 cup flour, 2/3 cup sugar, 1/4 cup butter, 1 egg, 1/2 tsp vanilla, 1 tsp baking powder, pinch salt, 1/3 cup milk.
Muffin tin: sugar-butter bottom, fruit, batter; bake 350°F 20 minutes, pop out. Benefits: Portion control for guilt-free indulgence, fun for events, same flavor punch.

Chocolate Swirl Pineapple Upside-Down Cake

Mid-century sin with chocolate batter ribbons. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple, cherries, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp vanilla, 2 tsp baking powder, 1/2 tsp salt, 3/4 cup milk, 2 tbsp cocoa + 1 tbsp milk.
Fruit base; swirl cocoa mix into plain batter, bake 350°F 40 minutes. Benefits: Antioxidants from chocolate, decadent yet balanced, kid-approved upgrade.

Lemon-Glazed Pineapple Upside-Down Cake

Bright 1950s tea time refresher. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple, cherries, 1 1/2 cups flour, 1 cup sugar, 1/3 cup butter, 2 eggs, 1 tsp lemon zest + vanilla, 2 tsp baking powder, 1/2 tsp salt, 3/4 cup milk; glaze: 1/2 cup powdered sugar + 2 tbsp lemon juice.
Standard bake 350°F 35 minutes, flip, drizzle glaze. Benefits: Vitamin C from lemon brightens, cuts richness, zesty twist for spring.

Peanut Butter Ripple Pineapple Upside-Down Cake

Bold 1960s lunchbox fusion. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1 can pineapple, cherries, 1 1/2 cups flour, 3/4 cup sugar, 1/3 cup butter + 1/4 cup peanut butter, 2 eggs, 1 tsp vanilla, 2 tsp baking powder, 1/2 tsp salt, 3/4 cup milk.
Ripple PB into batter; fruit base, bake 350°F 40 minutes. Benefits: Protein-packed for satiety, playful savory-sweet, nostalgic comfort.

These retro pineapple upside-down cake recipes are a delicious dive into yesteryear—easy to whip up with everyday ingredients and guaranteed to wow at your next gathering. Dust off that skillet, channel some vintage charm, and treat yourself or loved ones to a slice of history today!