Old School Sweets for my Sweetie

This week was full of celebrations for me and Mr. Food It Yourself. We celebrated our 9th wedding anniversary with grilled cheese sandwiches and tomato soup. We also celebrated Mr. Food It Yourself’s birthday. As the Birthday Haver he was entitled to choose the variety of cake that would be eaten. He chose a classic: pineapple upside-down cake. This made me especially happy because 1. I like vintage recipes and 2. I am really bad at icing cakes. Pineapple upside-down cake is a winner on both counts.

How did this classic, sticky, kitschy sweet come to be so well loved? The concept is really, really old. The idea really took off once canned pineapple became widely available. Karen Hammonds did a ton of research and posted it on her amazing blog Revolutionary Pie.

I had never attempted any type of upside-down cake before. As with any classic dish there are countless variations to the recipe for pineapple upside-down cake.  I started weeks ahead wading through the numerous choices on the internet. My one non-negotiable criterion was a recipe that did not use a boxed cake mix. Because…you know…DIYet and such.

I finally settled on this unfussy version from Food.com.  Since we invited guests over I wanted to make sure there would be enough for everyone. The comments section noted that this recipe could be successfully doubled. Further, the recipe does not call for weird stuff- no nuts, no funky spices, no rum agricole (whatever that is). This is a simple, standard, cake

Before I hit the kitchen I finished reading the comments section.  Some noted that the brown sugar and butter mix as prescribed in the recipe was excessive. Other comments mentioned that the cake itself was too sweet. After thoughtful consideration I came up with the following doubled recipe:

For the topping:

  • 1/3 cup* non-dairy butter replacer (one of our guests cannot have dairy)
  • 1 ½ cup brown sugar
  • 2 cans of 20 oz each pineapple rings
  • 1 20 oz can crushed pineapple**

*I didn’t see the need to double what many called excessive topping, but ¼ cup of butter did not seem sufficient to spread the quantity of brown sugar across the pan I planned to use.

**The crushed pineapple is an idea I stole from another version. You tuck the drained crushed pineapple in between the artfully arranged rings to ensure pineappley tastiness in every bite. Who needs those weird, atomic red “cherries”?

For the cake:

  • ½ cups non-dairy butter replacer
  • 1 ½ cup white sugar
  • 6 eggs
  • 1 cup pineapple juice
  • 2 tsp vanilla
  • 3 cups all-purpose flour
  • 4 tsp baking soda
  • ½ tsp salt

For the method, I pretty much followed the directions in the recipe.  Here’s what happened…

More wisdom from the comments section: drain the pineapple thoroughly. Otherwise, you will have soggy cake. Note the bowl under the strainer to retain the juice for the batter.


It takes a few minutes for the butter to melt and the sugar to smooth out. I picked out a couple hard lumps that I could not smoosh.


I took plenty of time to arrange the pineapple rings. This is where pretty counts.

With the topping done it was time for the batter. I am lucky enough to own a decent stand mixer for assembling my batter. I have done the first step- creaming the butter and sugar together- by hand. I can wholeheartedly say that this is a time to embrace technology. Look how fast it goes!

Just before I added the batter, I rubbed a little butter on the edge of the pan. My skillet is well seasoned, but I am still wary.

The over-sized cake took an extra 20 minutes to bake (55minutes vs. 35 noted in the original recipe). Nothing smelled burnt, so I was not too worried.


Here it is- Mr. Food It Yourself had to flip the pan, I just couldn’t control a cake that big in a skillet that heavy. If you are wondering about the edges…


The edges stayed in the pan. I must remember to butter the edges of the skillet a little more heavily next time.

The cake tasted wonderful.  I think the sweetness was just right; I like a less-sweet cake.  The texture was a little muffin-ish though, which means I under mixed the batter. I’ll remember to mix longer next time. Mr. Food It Yourself was happy with is birthday treat, which is what really matters. The only major disappointment was that several of our guests were unable to attend.  On the plus side, we have leftovers!

I enjoyed making this cake for Mr. Food It Yourself, and I enjoyed sharing it with our family. I now have a really good dessert-for-a-crowd recipe, too.  What was the best “special request” you ever made for someone? Share in the comments!