Fresh Pineapple Upside-Down Cake

IMG_0016I recently had one of those humbling moments. One of those moments when you realize just how stubborn and ignorant you were as a child. Suddenly, all the times that you’ve rolled your eyes at a picky child throwing a tantrum come rushing back to you and you see your very own hypocrisy staring back at you. I’ve had many of these moments, mind you. I think maybe some of us develop our palettes a little more gradually than others. Whatever the case may be, I’ve slowly come to adore certain foods that I would’ve run kicking and screaming from as a child. To name a few: mustard, lettuce, oranges, corn, tomatoes, raw onions, mushrooms, asparagus… need I go on?

If you had asked me, I would have told you that I was not a picky eater as a child. I reasoned that we all have our likes and dislikes — how can you judge someone as “picky” just for following their own tastes? Besides, I was clearly not a picky eater growing up. No, I was a plump, nearly rotund specimen of food-loving boyhood! There were just certain foods I did not like. Period. Right?

Gradually, though, re-exposure to foods I’d formerly rejected began to change my perspective. Whether it was peer pressure or embarrassment that first caused me to take a bite of asparagus (for example), I can’t recall, but I do know that I’ve been rather hooked on it ever since. And after swearing that I couldn’t bear the texture of biting into fleshy, indigestible orange pulp, I one day found myself shoving slice after slice of navel orange into my mouth absentmindedly as I was slicing an orange to “flavor” some strawberry tea.


But, I digress. My most recent fascination/discovery with a formerly rejected food: pineapple. Fresh pineapple, to be exact. It all started when my boss brought back two pineapples from Hawaii and deposited them in the break room. “What is that tart, exotic perfume I smell?!” begged my senses. I took a slice… and then another, and then another. I’m totally hooked, now. So, while I’m waiting for locally grown fruit to come into season here in the Midwest, I’m allowing myself to enjoy a few fresh pineapples from other parts of the globe.

Why was I so against pineapple in the first place? Maybe it was owing to my first few introductions to the fruit — all of which was canned. Those tough, sinewy pieces in the canned fruit cocktail, all slimy and glistening in IMG_2856heavy syrup. The metallic-smelling, stomach-burning sensation of canned pineapple juice. The forlorn look of canned pineapple rings clinging to the side of a baked ham. None of it just screamed “Eat me!” to little childhood me. So, naturally, I turned my nose up at Maw Maw Vern’s Pineapple Cake. Surely it was an abomination — probably the ONLY dessert that I wouldn’t touch. I look back wistfully, now, at how my stubbornness probably hurt my grandmother’s feelings — this cake being one of her signature dishes.

Thank goodness Maw Maw Vern is still with us and I can now face her cake with gratitude rather than fear. In fact, she made one “just for me” recently, when James and I visited Louisiana. Clearly she’d forgotten that I IMG_2851never used to like it (perhaps this is where I get my selective memory from?). At least I’ve matured over the years. It wouldn’t have been fitting to cry into my dessert plate with pouty lips and furrowed brow, would it?

Maw Maw’s cake is a pretty simple one — a basic one or two-layer white cake (usually made from Pioneer Baking Mix) baked and then topped with simmered, sweetened, canned crushed pineapple. If I’m not mistaken, her cake used to be a more traditional “upside-down” cake, but she has gradually tweaked it over the years to something all her own creation.

In March, I sat at the table near her (the table which she’d lovingly decorated with the tablecloth I’d helped my great-aunt sew when I was in junior high), and ate a slice of her cake. I was happy to finally be in on the fun. She, of course, did not realize this was the first time I wasn’t choking it down. And I was happy to be able to tell her (and IMG_3432sincerely mean it), “This is really good, Maw Maw!” Her smile and the glint of pride in her eyes was a reward all its own.

Of course, all of this got me to brainstorming about marrying my new-found love of fresh pineapple with my former nemesis the Upside-Down Cake. You can imagine my delight when I came across a recipe in a recent issue of Cook’s Country that used frozen pineapple and allowed for the use of fresh pineapple as a substitution! I made a few tweaks to the recipe and decided to give it a go. From the moment the fresh pineapple met with the brown sugar in the hot skillet, I knew we were in for a treat!


Like Maw Maw’s famous cake, this recipe is extremely simple. I loved how the cake required very little advanced preparation — none of that softened butter creamed into sugar… blah blah blah. No, this recipe comes together and goes into the oven in a flash! Perhaps the best part, though, was that this recipe was a reduced-fat version. Yes indeed! It’s almost health food, right?

Fresh Pineapple Upside-Down Cake
Adapted from Cook’s Country
Serves 8

    Pineapple Topping:
    4 cups chopped fresh pineapple (approximately one pineapple)
    1/3 cup light brown sugar
    1 1/2 tablespoons unsalted butter
    2 teaspoons lemon juice
    1/2 teaspoon vanilla extract

    1/2 cup all-purpose flour
    1/2 cup whole wheat pastry flour
    1 teaspoon baking powder
    1/2 teaspoon salt
    1/2 cup low fat sour cream
    1/2 cup granulated sugar
    1/4 cup brown sugar
    2 large eggs
    1 1/2 teaspoons vanilla extract
    4 tablespoons unsalted butter, melted

    Preheat oven to 350-degrees. Lightly grease a 9-inch cake pan, set aside.

    To prepare the topping, cook the chopped pineapple and brown sugar in a large non-stick skillet over medium-high heat, stirring occasionally, until pineapple is slightly browned and juices are nearly evaporated (10-15 minutes). Remove from heat, stir in butter, lemon juice, and vanilla; pour directly into prepared cake pan, spread evenly.

    To prepare the cake, combine the flours, baking powder, and salt in a medium bowl. In a larger bowl, whisk together the sour cream, brown sugar, eggs, and vanilla until smooth. While whisking the mixture, slowly add the melted butter until incorporated. Stir the flour mixture into the sour cream mixture mixing just until combined. Scrape batter into cake pan, spreading to cover pineapple mixture.

    Bake in preheated oven until cake is golden (25-30 minutes) and a toothpick inserted in the center comes out clean. Cool cake in pan on a wire rack for 10 minutes; then turn out onto platter. Allow cake to cool at least one hour before serving. Store leftover cake loosely covered in refrigerator.


If the smell of the cake baking and melding with with caramelizing fresh pineapple doesn’t cause you to nearly melt, then the taste of the finished product surely will! One bite and you’ll definitely taste the difference fresh pineapple makes. The flat, sugary taste you might associate with Pineapple Upside-Down Cake is completely missing and is replaced with a complex, tart-floral one that is complemented with a sinful-tasting cake. You’ll be glad to know that the leftovers will last you most of the week if kept lightly covered in the refrigerator.

Since pineapples are an exotic, non-local indulgence, James and I pledge to make this a “special occasion” dessert. Maybe you’d like to try it, soon, for one of yours?

Approximate nutrition facts: (per slice) 315 calories, 11g of fat [7g sat., 3g mono., 1g poly], and 2g of fiber.

Photo Credit: The first photo in this entry was taken by my mother on a family vacation somewhere in the mid 1980s. That’s me, squinting in the gulf coast sun and my little brother, Andy, making an equally photogenic face.


~ by Jason on May 17, 2011.

2 Responses to “Fresh Pineapple Upside-Down Cake”

  1. Love the Rocky Jr. t-shirt. As a picky kid, I can relate. Trying things I didn’t like is a new adventure now.

    • Ha! I think my little brother was wearing that shirt as a hand-me-down from my older brother!

      I like to think that maybe holding out on trying those foods when I was younger might be what makes food so interesting and exciting to me, now.

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