For the fourth installment of the #BakingWithBeth series, we’re sticking with the classic, old-fashion cake theme one more time and making a pineapple upside down cake. There will still be more cake throughout the series. And likely Definitely more cakes from old southern and church cookbook recipes. As I’ve let nostalgia guide the beginning of the series, week four is dedicated to the first cake I ever baked.
A pineapple upside down cake might not be the first cake I ever baked, but it’s the first cake I remember baking on my own. Pineapple upside down cake is one of my mom’s favorite cakes, which I baked for her birthday. There’s a good chance I took the quick route and used a box cake mix instead of making the cake batter from scratch. However, if I can’t fully remember…we can just go with from scratch, right?! Haha. 😉
Cooking a cake upside down with the fruit and sugar at the bottom is an old method that got it start in American when cakes were cooked in cast iron skillets. They could be cooked on a stovetop or over a fire and then flipped over to show off the fruit. In 1911, one of James Dole’s engineers invented a machine to cut pineapples into rings. After which pineapples were added as a fruit to the cast iron skillet cake. The pineapple upside down cake began gaining popularity in the States in the 1920s
Historically, upside down cakes date back even further to Normandy, France with desserts like the Tarte Tatin (1880s). And even further back to the father of haute cuisine, Marie Antonie Carême. Carême mentions gâteaux renversés in his 1815 cookbook, Le Patissier Royal Parisien.
For this pineapple upside down cake, I consulted my Grandmother’s copy of Mrs. S.R. Dull’s Southern Cooking from 1968. Given to her by my Grandfather in 1973 with the inscription, “To Eugenia, With all my love! Lee 12/25/73” A cookbook that’s tattered and interesting to intemperate some of the recipes and methods, but one I’ll always cherish in my collection.
Prepping for the pineapple upside down cake resulted in online recipe research. I didn’t like any of them, so I took the basis of Mrs. S.R. Dull and revamped it. The result was quite nice!
The original recipe called for the liquid being entirely milk, but I thought it would be fun to see how some pineapple juice would work in tandem. Also, I had eight pineapples and only needed seven, so I diced up the last pineapple and stirred it in at the end.
Specialty Tools Needed:
- Cast Iron Skillet (one of my favorite kitchen items!)
Thanks again for coming back for another #BakingWithBeth recipe. Just to recap: week one/caramel cake, week two/Hummingbird Cake and week three/sour cream pound cake. Pineapple Upside Down Cake recipe below. Can’t wait to hear your feedback!
Be sure to follow along Instagram and Facebook and tag #BakingWithBeth so I can see all the fun treats y’all make!
Have y’all tried pineapple upside down cake? Any recipe variations I should try? I made them in cupcake form once & those might be on repeat very soon!
Cheers y’all!

Pineapple Upside Down Cake
Ingredients
- 57 grams butter (4 TBSP)
- 110 grams light brown sugar (1/2 cup)
- 7 slices pineapple rings
- 14 each Maraschino cherries
- 40 grams chopped pecans, optional (1/3 cup)
- 105 grams sugar (just shy 1/2 cup)
- 15 grams butter (1 TBSP)
- 1/2 tsp vanilla extract
- 1 each egg
- 210 grams all-purpose flour (1 & 1/4 cup)
- 2 tsp baking powder
- 1/4 tsp salt
- 65 grams milk (approx 1/3 cup)
- 50 grams pineapple juice (reserved from can) (approx 1/4 cup)
- 35 grams pineapple bits (1 pineapple ring chopped small)
Instructions
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Melt butter in a cast iron skillet over a low heat. Once melted remove from heat and shake to evenly coat the bottom of the skillet. Sprinkle brown sugar evenly on the bottom. Place pineapple rings on top of the brown sugar, starting in the center. Place the cherries in the center of each pineapple and in the gaps along the edge. Sprinkle chopped pecans in between the gaps of the pineapple and cherries (optional).
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Sift together flour, baking powder and salt. Set aside. In a mixing bowl, cream together butter and sugar. Add egg and vanilla and mix on low until incorporated. Scrape down. On low speed add flour mixture and alternate with milk and pineapple juice after each flour addition. Stir in pineapple bits and pour batter over pineapples in the skillet.
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Bake at 325 degrees Fahrenheit for 40 minutes, or until a wooden pick comes out clean. Let cool and then flip over onto serving platter. Serve and enjoy!