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A classic pineapple upside down cake topped with caramelized pineapple rings and maraschino cherries, inspired by the original 1925 recipe.

Pineapple Upside Down Cake

Olivia Carter
gooey caramelized pineapple rings topped with those cheeky maraschino cherries, all hugged by a super moist vanilla cake. It's the dessert that stole America's heart back in 1925—timeless, baby!
20 minutes
Prep Time 20 minutes
Cook Time 45 minutes
Chill Time 20 minutes
Total Time 1 hour 25 minutes
COST Around $8–$12
Course Dessert
Cuisine American
Keyword Pineapple upside down cake
Servings 8 lucky folks
Calories 360 kcal

Equipment

  • 9-inch round cake pan
  • A couple of mixing bowls
  • Electric Mixer or Whisk
  • rubber spatula
  • Measuring cups & spoons
  • Cooling rack
  • A plate for the big flip moment

Ingredients
  

For the drool-worthy topping:

  • ¼ cup unsalted butter, melted
  • ½ cup packed brown sugar
  • 1 can pineapple rings in juice juice, not syrup—syrup's a soggy buzzkill
  • 12 maraschino cherries go wild, they're the party hats

For the cake batter (moist and fluffy):

  • cups cake flour or all-purpose
  • 1 tsp baking powder
  • ¼ tsp baking soda
  • ¼ tsp salt
  • 6 tbsp unsalted butter, softened
  • ¾ cup granulated sugar
  • 2 large eggs, room temp
  • cup sour cream or plain yogurt
  • ¼ cup pineapple juice save it from the can!
  • 2 tbsp milk
  • 1 tsp vanilla extract

Instructions
 

  • Topping time: Crank your oven to 350°F (177°C). Dump that melted butter in the pan, and sprinkle brown sugar all over it like you're making sweet sand.
  • Fruit party: Dry those pineapple rings and cherries super well. Pat them like a pro—no wet drama. Line up the rings on the sugar, and plop cherries in the middles. Boom, now it looks insta-pretty.
  • Dry squad: Whisk flour, baking powder, baking soda, and salt in a bowl. Easy peasy.
  • Wet squad: In another bowl, mix sour cream, pineapple juice, milk, and vanilla. Smells like vacation already.
  • Butter bliss: Beat the softened butter and sugar till it's fluffy and pale—about 2 mins. (Pretend you're stress-baking your worries away.)
  • Eggs in: Crack in eggs one by one, and beat well each time. No lumps, champ!
  • Batter magic: Add dry and wet mixes to the butter alternately—start and end with dry. Stir just till it comes together. Overmix and it's tough love.
  • Layer up: Gently spread batter over the fruit. Smooth the top like a zen master.
  • Bake it: 30 mins first, then tent with foil (no burnt top tragedy). Another 13–18 mins till a toothpick's mostly clean. Smells insane, right?
  • Cool & flip drama: 20 mins cool time. Knife around edges, plate on top, flip! (I've flipped fails before—warm is key for caramel magic.)
  • Serve: Let it chill fully before slicing. Warm or room temp? Both slap.

Notes

  • Juice-packed pineapple only—syrup makes it cloyingly sweet and mushy.
  • Dry that fruit like your flip depending on it (it does).
  • Flip warm (15–20 mins post-oven) so caramel doesn't stick like a bad date.
  • Best same day, but covered at room temp for 24 hrs max. Leftovers? Reheat gently.

Per Slice (Rough Guess):

  • Calories: 360
  • Carbs: 52g
  • Protein: 4g
  • Fat: 16g (9g sat)
  • Cholesterol: 75mg
  • Sugar: 36g
  • Fiber: 1.5g
  • Sodium: 180mg
(Tweak based on your brands—it's dessert, live a little!)