The Show Girl & Pineapple Upside Down Cake

The Show Girl & Pineapple Upside Down Cake

The Show Girl by Nicola Harrison follows Olive McCormick in 1927 as she moves from Minneapolis to New York City in search of fame. When I first started reading this book, I had one thing in mind — what would pair perfectly with a story set during this time period? After going back and forth with some ideas, I chose a Pineapple Upside Down cake for the #showgirlparty with The Book Club Cook Book.

These cakes are easy to make and full of sweet pineapple taste. But, did you know that Pineapple Upside Down cakes became wildly popular in 20’s?  In 1925, the Hawaiian Pineapple Company sponsored a contest calling for pineapple recipes with judges from the Fannie Farmer’s School, Good Housekeeping, and McCall’s Magazine on the judging panel.  Several of the submissions were recipes for Pineapple Upside-Down cake — after that contest, the company ran an ad about the sweet pineapple cakes and the cakes became a staple dessert in homes. 


  • 1 Box Yellow Cake Mix + Ingredients to make Cake (Eggs + Oil)
  • 1 Can Pineapple Rings (20oz)
  • 1 small jar of Maraschino Cherries
  • 3 tbs unsalted butter
  • 1/3 Cup Brown Sugar


  1. Preheat Oven to 350°
  2. Open pineapple rings and drain juice into a bowl, set aside.
  3. Slice pineapple rings in half, set aside.
  4. In a small sauce pan, melt 2 tbs butter and brown sugar until evenly melted. Pour evenly into a greased 10” Bundt pan.
  5. Stand pineapple rings in a circular design around the Bundt pan (one every 1/2 inch to an inch) adding one cherry between each slice of pineapple.
  6. Add cake mix, eggs, oil and substitute the reserved pineapple juice for the water to make batter in bowl. If there is not enough juice, use the remainder with water.
  7. Pour batter slowly into pan (I usually pour it in between each pineapple piece and then slowly pour over the top). If the rings starts follow, take a fork and place them upright. 
  8. Bake for 35 – 45 mins. 
  9. Remove from oven and let cool for 20 minutes.
  10. Take a knife and easily run it between cake and pan. 
  11. Place a plate over the top of the cake and then carefully flip onto pan. 
  12. Enjoy!

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