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Dole

Dole Crushed Pineapple Upside-Down Cake

Adapted from the original Dole Dole Canned Sliced Pineapple packaging. Back of the Bag is not affiliated with Dole.

"The skillet-baked classic that defined mid-century hospitality."

Prep 20 min Cook 45 min 9 servings
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Dole Crushed Pineapple Upside-Down Cake

The Story

Following a 1925 recipe contest held by the Hawaiian Pineapple Company (later Dole), this dish became an overnight sensation. Of the 60,000 entries, over 2,500 were for Pineapple Upside-Down Cake, leading the company to feature it prominently in advertisements and on can labels throughout the following decades.

From the back of Dole Canned Sliced Pineapple — since 1925

Ingredients

  • 1/4 cup butter or margarine
  • 2/3 cup packed brown sugar
  • 1 can (20 oz.) Dole Pineapple Slices
  • Maraschino cherries
  • 1 1/3 cups all-purpose flour
  • 1 cup granulated sugar
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/3 cup shortening
  • 2/3 cup milk
  • 1 egg

Directions

  1. 1

    Preheat oven to 350°F.

  2. 2

    Melt butter in a 9-inch square pan or oven-safe skillet; sprinkle brown sugar evenly over butter.

  3. 3

    Drain pineapple, reserving juice. Arrange slices on top of sugar; place a cherry in the center of each slice.

  4. 4

    In a bowl, combine flour, sugar, baking powder, and salt. Add shortening, milk, and 3 tablespoons of reserved pineapple juice.

  5. 5

    Beat for 2 minutes, add the egg, and beat for 2 more minutes.

  6. 6

    Pour batter over pineapple slices.

  7. 7

    Bake for 40 to 45 minutes or until a toothpick comes out clean.

  8. 8

    Let stand for 5 minutes, then invert onto a serving plate.