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Classic Pineapple Upside-Down Cake Recipe for Moist, Old-Fashioned Flavor

I’m starting a vintage recipe series — here’s the first one! This classic pineapple upside-down cake is simple and delicious. It uses a box of yellow cake mix, canned pineapple slices (and their juice instead of water), brown sugar, melted butter, and maraschino cherries, plus the eggs and oil called for on the cake mix box. The pineapple juice adds real flavor, and this cake turned out to be one of my favorites. Early cake mixes date back to the 1930s, so this shortcut still fits the vintage theme. Let’s bake!

Vintage Pineapple upside down cake
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Video

A pineapple upside-down bundt cake topped with pineapple rings and red maraschino cherries, displayed on a white plate over a yellow cloth with red cherry patterns.

Vintage Pineapple Upside Down Cake

Melissa Jo

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Ingredients

  • 1
    box yellow cake mix
  • eggs and 1/2 cup oil as directed on cake mix box
  • pineapple juice from canned slices (replace the water called for on the box)
    If your can doesn’t yield a full cup, top up with water. A 20 oz can typically provides enough juice for the full cup.
  • 1/2
    cup
    melted butter (about 1 stick if salted)
  • 1/2
    cup
    brown sugar
  • 20
    oz.
    can pineapple slices packed in 100% juice
  • 6–7
    maraschino cherries
  • Pam or butter to grease the bundt pan
    Use plenty so the cake releases easily.

Instructions

  • Preheat oven to 350°F (180°C).
  • Prepare the cake mix according to the package, substituting the reserved pineapple juice for the same amount of water. Add the eggs and oil as the box directs.
  • In a separate bowl, combine the melted butter and brown sugar until smooth.
  • Pour the butter and brown sugar mixture evenly into the bottom of a well-greased bundt pan.
  • Arrange pineapple slices in a single layer over the butter and brown sugar. Place a cherry half in the center of each slice.
  • Pour the prepared cake batter evenly over the pineapple and cherries.
  • Bake 40–45 minutes, or until a toothpick inserted in the center comes out clean.
  • Remove from oven and let cool 5 minutes. Invert the bundt pan onto a serving platter and allow the cake to cool completely before serving.
  • Slice and enjoy!

Notes

  • Use pineapple slices packed in 100% juice, not heavy syrup. Reserve the juice and use it in place of the water called for on the cake mix.
  • If your can doesn’t provide a full cup of juice, top up to 1 cup with water — this still tastes great. A 20 oz can usually supplies enough juice for the full cup.
  • A bundt pan works beautifully for presentation and gives a classic vintage look.


Tried this recipe?
Let us know how it was!