Pineapple Upside Down Loaf

Pineapple Upside Down Loaf
  • Yield : 1 regular loaf
  • Servings : 8-10
  • Prep Time : 20m
  • Cook Time : 1:30 h
  • Ready In : 3:0 h

Just like the iconic skillet cake, this loaf has crushed pineapple, and bright red maraschino cherries as the topping. Same flavors none of the fuss though if transporting to a family dinner. In fact, bake it in a disposable pan, and you won’t even have to worry about remembering your dish when you get ready to come home. You may notice the stems in the picture, and the recipe indicates non stemmed cherries. Be a rebel like me, by removing the stems from maraschino cherries and setting aside on a paper towel. Proceed with recipe. When cool, use a toothpick to re-poke the holes in the cherries, re-insert stems, there ya go, a gourmet touch!


  • Topping:
  • 1 20 oz can crushed pineapple, drained, reserve 2 TB juice
  • 3 TB unsalted butter
  • 2 TB granulated sugar
  • 6 maraschino cherries without stems, patted dry (double the number if you like them)
  • Batter:
  • 1 cup granulated sugar
  • 1 cup (2 sticks) unsalted butter, room temperature
  • 4 large eggs
  • 2 cups self-rising flour
  • 1 tsp baking powder


Step 1

Preheat oven to 325 degrees. Spray a loaf pan with non stick baking spray. Set aside.

Step 2

Prepare upside down topping by heating pineapple, butter, and sugar together in a a medium saucepan set over medium high heat. Once sugar has dissolved, remove from heat.

Step 3

In the bowl of a stand mixer, beat together sugar, and butter until light and fluffy.

Step 4

Beat in eggs one at a time. Whisk together flour and baking powder in a separate bowl then gradually add to bowl. Add reserved pineapple juice. Turn mixer to medium high speed, and beat for 30 seconds.

Step 5

Pour pineapple mixture into bottom of prepared loaf pan. Nestle cherries in the center stem side down. If using six, space apart evenly. If using twelve, just make sure to center perfectly.

Step 6

Carefully pour batter over top being careful not to jostle cherries. Bake for 1 hour and 15 minutes. Check temperature with an instant read thermometer. If it has not reached 185-190, continue to bake an additional 15 minutes, checking temperature again after 10 minutes. Allow cake to cool for 10 minutes before turning out of pan.

Step 7

Don't be timid about turning this loaf out. Simply turn out onto a piece of parchment paper or wax paper then quickly turn pineapple side up. Remove any sticking pineapple from pan and rearrange on top. Allow to cool at least 10 minutes before slicing.

Step 8

Store covered in the refrigerator.

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