12 Upside-Down Desserts Your Family Will Flip For

Southern Living Pineapple Upside Down Dump Cake whole and ready to serve

Stacy K. Allen; Food Stylist: Chelsea Zimmer; Prop Stylist: Christine Keely

While Southerners love a perfectly executed Caramel Cake or a delicious Peach Cobbler, there is something to be said for upside-down desserts. What makes these desserts upside-down you may ask? The topping on all of these desserts actually starts in the bottom of the pan. After baking, the dessert is flipped, revealing a delicious, caramelized layer of syrupy goodness that can only be created by baking the dessert the “wrong” way. This retro technique is unusual, but it yields a delicious result that most Southern grandparents have served their guests for generations and for good reason. Traditionally, you may think of upside down cakes solely as Pineapple Upside-Down Cake, while we have included several variations in this list (including a cast-iron skillet version) there are a wide variety of baked goods that can be baked with this technique that go beyond canned pineapple. From Mini Grapefruit Upside-Down Cakes to Rhubarb-Buttermilk Upside-Down Cake, we’ve got delicious desserts that are sure to delight your dinner party guests. 

01 of 12

Pineapple Upside-Down Cake

Pineapple Upside-Down Cake
Photographer: Jennifer Causey Food Stylist: Ana Kelly Prop Stylist: Kay Clarke

Our classic take on an upside-down dessert might just be the perfect ending to dinner with your supper club. Everything about this recipe is totally retro, from the canned pineapple rings to the 12 maraschino cherries.

02 of 12

Cinnamon Upside-Down Coffee Cake

Cinnamon Upside Down Coffee Cake
Photography: Caitlin Bensel, Food Styling: Emily Nabors Hall

You can serve this Cinnamon Upside-Down Coffee Cake with tea or brunch, and everyone will be asking you what's your secret to the perfectly caramelized exterior and pillowy center. Of course, it's that nutty topping that starts on the bottom of your greased pans! The recipe makes two batches, one for you and one for your neighbor.

03 of 12

Pineapple Upside-Down Dump Cake

Southern Living Pineapple Upside Down Dump Cake whole and ready to serve

Stacy K. Allen; Food Stylist: Chelsea Zimmer; Prop Stylist: Christine Keely

Sometimes we don't have the time to bake a cake from scratch, and our Pineapple Upside-Down Dump Cake is the perfect solution. Just like most other dump cakes, you pour in a boxed cake mix as well as some canned fruit and you're done. No need to mix.

04 of 12

Peach-Bourbon Upside-Down Bundt Cake

Peach-Bourbon Upside-Down Bundt Cake

Do something surprising with your fresh, summer peaches and make our Peach-Bourbon Upside-Down Bundt Cake. The caramelized peaches work perfectly with the dense pound cake and make this a summer treat you won't soon forget.

05 of 12

Pineapple-Ginger Upside-Down Cake

Pineapple-Ginger Upside-Down Cake

It's no secret that Southerner's love this technique because of the sticky caramelized layer of fruit, so in this recipe we've doubled up on that goodness. We've replaced the bright red artificial maraschino cherries with a more adult twist of freshly grated ginger and traded canned pineapple for fresh to make this dessert go from retro to elevated.

06 of 12

Mini Grapefruit Upside-Down Cakes

Mini grapefruit upside-down cakes on pink plates

Antonis Achilleos; Prop Stylist: Audrey Davis; Food Stylist: Torie Cox

Make something personal for your guests with these individually sized Mini Grapefruit Upside-Down Cakes. Full of citrus and syrupy sweet flavor, topping these little cakes with a dollop of whipped cream will make them some of the cutest cakes of all.

07 of 12

Pear Upside-Down Cake

pear upside down cake
Photographer: Isaac Nunn, Prop Stylist: Julia Bayless, Food Stylist: Ruth Blackburn

We've fallen in love with this autumnal twist on upside-down cake with pears and warm flavors like cinnamon and cardamom. To get the thinnest slices, we recommend using a mandolin.

08 of 12

Blueberry-Honey Upside Down Cake

Blueberry-Honey Upside Down Cake
Antonis Achilleos; Food Styling: Emily Nabors Hall; Prop Styling: Audrey Davis

We know fruits from pineapple to pears to grapefruit yield a successful result when it comes to upside-down baking, but blueberries also benefit from this sort of treatment. The blueberries soften and caramelize, turning your regular sweet blueberries into something with even more of a twist.

09 of 12

Honey-Pineapple Upside-Down Cake

Honey-Pineapple Upside-Down Cake

Hector Sanchez

To get the syrup-filled dessert you are looking for, you can opt for something a little more natural with an ingredient that will still give you caramelized results: honey. We used canned pineapple for this version, but fresh will work just as well here.

10 of 12

Cranberry Upside-Down Cake

Cranberry Upside-Down Cake
Oxmoor House

Did you know that you can make upside-down cake in a slow cooker? Yes, you can. Our Cranberry Upside-Down Cake is just as simple as it can get using boxed pound cake mix.

11 of 12

Rhubarb-Buttermilk Upside-Down Cake

Rhubarb-Buttermilk Upside-Down Cake
Antonis Achilleos; Food Styling: Chelsea Zimmer; Prop Styling: Christine Keely

Looking for a recipe that's almost too perfect to eat? This pretty in pink Rhubarb-Buttermilk Upside-Down Cake is just what you need to serve to your guests. We promise that while it looks beautiful, it's not overly complicated.

12 of 12

Pineapple Upside-Down Cake

Pineapple-Upside Down Cake
Jennifer Davick

We've put a classic Pineapple Upside-Down Cake in as cast-iron skillet, and we promise it's the only way you'll want dessert from now on. The well-seasoned pan with the caramelized goodness of the fruit lends itself to the most unbelievable combination.

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