Food You Can Eat: Pineapple Upside Down Bundt Cake

Good, sticky, fun!

There may have been other versions of this cake in FYCE history (Mattie?) but this one is worthy of inclusion. Caveat – please get yourself a Bundt pan – they are inexpensive, and any cake can be converted to a one-pan Bundt recipe.

Preheat your oven to 350 degrees and grease your Bundt pan, getting all the nooks and crannies.

Pour 1/2  cup melted butter in the bottom of the pan, and sprinkle 2/3 cup brown sugar over the butter. Arrange a 20-ounce can of drained pineapple rings around the bottom of the pan. Add 18+ maraschino cherries around the pineapple rings. I put two in each center (they will sink while baking) and two on each side of the rings.

Now for the annoying part, if, like me, you do not own a stand mixer. Mix together 1/2 cup of unsalted butter and 1 and 1/2 cups of sugar for…10 minutes, until creamy. This makes a big difference in the outcome, do not scrimp on the mixing time. Mix in a well-drained 20-ounce can of crushed pineapple (maybe even blot out excess juice on a towel), 2 eggs, and 1 teaspoon vanilla extract.

In a separate bowl, mix 2 and 1/4 cups cake flour (it really should be cake, not regular flour), 2 and ½ teaspoons baking powder, and 1 teaspoon salt.

Alternately mix the dry ingredients and 1 and 1/4 cups milk, into the wet ingredients, beating until smooth.

Pour it into the Bundt pan and bake for 40 minutes – the edges should bubble, and a skewer should come out clean. Cool for about 15 minutes, then flip onto a serving plate (do not over cool, as the topping will harden, and the cake will be a pain to get out of the pan).

Looks pretty, tastes great!

About Elliecoo 505 Articles
Four dogs, one partner. The dogs win.


  1. Pineapple Upside Down Cake was my father’s favorite. I always made it for his birthday. Like you I love my Bundt Pan so I will be trying this version. 
    *psst @KeitelBlacksmith, a KitchenAid stand mixer would make a great Christmas gift for Ellie! Watch for sales!*

  2. You rang?

    But I’m sure yours is 100% better because you actually put effort into it.

    I love Bundt pans. Have you ever made a timbale? I’ll have to dig up my recipe, although there are dozens if not hundreds out there. It is made in a Bundt pan, although I suppose it could be adapted to something more hum-drum, like a 13 X 9 pan.

    BTW, and I’m sure I’ll tire of this topic soon and stop pestering you all with it, another disappointment of the Sinatra Celebrity Cookbook is there is no Pineapple Upside Down Cake recipe. This is an egregious oversight. 

    But pineapple is not entirely ignored. Kathie Lee Gifford shares her Polynesian Chicken recipe, Henry Winkler has a recipe for Hawaiian Chicken, and Arnold Palmer comes out of left field (or the 19th hole)  with Hawaiian Meatballs with Sweet and Sour Sauce. 

    I may have to make one of these while Better Half is out of town because, much to my astonishment, he doesn’t really like pineapple. It is one of his few failings.

  3. We always do ours in a cast iron skillet that you get super hot so when you pour the stuff in it caramelizes. 

    However, this looks beautiful and I want to get a bundt pan and try it. Or more realistically, borrow a pan from my parents. 

Leave a Reply