Pineapple Right-Side Up Cake Recipe

This Pineapple Right-Side Up Cake Recipe combines caramelized pineapple, buttery vanilla cake, and a nostalgic yellow cake frosting for a tropical dessert with a modern twist. Featured on Cook the Books Season 3: Celebrity Edition, hosted by Shahir Massoud, this recipe from Party People brings together rich flavours and playful presentation for a show-stopping cake perfect for gatherings and special occasions.

The Inspiration

Traditional pineapple upside-down cake has long been loved for its combination of sweet pineapple, buttery caramel notes, and soft yellow cake. This recipe takes those comforting elements and reimagines them by roasting fresh pineapple before folding it into the cake batter and incorporating it into the frosting. The roasting process intensifies the pineapple’s natural sweetness while creating a deeper, richer tropical flavour.

Featured on Cook the Books Season 3: Celebrity Edition, hosted by Shahir Massoud, this recipe reflects the spirit of entertaining and bringing people together through food. The cookbook Party People focuses on approachable yet memorable dishes designed for celebrations, and this dessert perfectly captures that philosophy.

Ingredients

For the Pineapples

1 medium pineapple, cored and cut into ½ inch (1cm) chunks (about 6 cups/907g)
1/4 cup (60g) light brown sugar, firmly packed
¼ teaspoon kosher salt
2 tablespoons unsalted butter, cut into small chunks

For the Cake Batter

Butter or pan spray, for greasing
1 ½ sticks (12 tablespoons) unsalted butter, softened
1 ½ cups (300g) granulated sugar
1/3 cup (75g) light brown sugar, firmly packed
3 eggs
3 egg yolks
1 ½ tablespoons vanilla extract
½ cup (120ml) grapeseed or canola oil
2 ¼ cups (338g) cake flour
1 ½ teaspoons baking powder
1 ¼ teaspoons kosher salt
¾ teaspoon baking soda
1 cup (240ml) buttermilk

For the Yellow Cake Frosting

1 cup (160g) boxed yellow cake mix
2 sticks (16 tablespoons) unsalted butter, softened
1 cup (125g) confectioners’ sugar
1 tablespoon half-and-half
1 teaspoon vanilla extract
Maraschino cherries in their liquid

Method

Preheat the oven to 450F (230C). Line a baking sheet with parchment paper.

Make the Pineapples

Spread the pineapple chunks on a baking sheet.
Toss with the brown sugar and salt and then dot with the butter.
Bake for 45 to 55 minutes, tossing halfway through, until the pineapples are very soft and caramelized and most of the liquid has evaporated from the pan.
Remove from the oven, and use a spatula to scrape the pineapples and all the butter and sugary juices into a bowl or container.
Chill in the fridge for at leas 1 hour and up to 4 days.
Reduce the oven temperature to 350F (180C).
Grease a 9×13-inch (23x33cm) baking pan with butter or pan spray, and line the bottom with parchment paper.

Make the Cake Batter

Add the butter, granulated sugar, and brown sugar to the bowl of a stand mixer fitted with the paddle attachment. Start the mixer on low (so you don’t spray sugar everywhere) and then work your way up to high, add the cream until light, fluffy, and emulsified, about 4 minutes, stopping to scrape down the sides of the bowl a couple times.
Meanwhile, crack the eggs into a liquid measuring cup (it’s easier to add them this way), add the egg yolks, and measure the vanilla on top of the eggs.
Reduce the mixer speed to medium, and add the eggs, one or two at a time, waiting 10 to 15 seconds between additions and scraping down the sides of the bowl several times. Increase the speed to high and mix for about 30 seconds while you measure the oil into the liquid measuring cup. Reduce the speed to medium-low, and slowly drizzle in the oil. Ramp it back up to high, and let ‘er rip for a minute or two, until the mixture is very light and fluffy and gorgeous.
Meanwhile, whisk together the flour, baking powder, salt, and baking soda in a large bowl.
Measure the buttermilk into the now-empty liquid measuring cup. (See how we are saving you from creating a bunch of dirty dishes?)
Scrape down the sides of the mixer bowl, and with the mixer on low, add one-third of the flour mixture to the batter, then half of the buttermilk, then half of the remaining flour, then the rest of the buttermilk, and finally the last of the flour. Increase the mixer speed to medium, and mix for about 30 seconds to make sure the batter is evenly combined. Scrape he bowl one last time, all the way down to the bottom, and if you notice any streaks, do any extra mixing by hand.
Measure out 1 ½ cups (240g) of the roasted pineapple, finely chop it, add it to the batter, and mix on low until evenly combined.
Pour the batter into a prepared pan, and use a spoon or spatula to make sure it’s evenly distributed. Bake for about 40 minutes, rotating after 30 minutes, until the cake starts to brown on the edges, bounces back slightly when you press the top, and just starts to pull away from the sides.
Remove from the oven, and let it cool to room temperature. Transfer to the fridge to chill for 2 hours.
Preheat the oven to 325 F (165C)

Make the Frosting

Evenly spread the yellow cake mix into a baking sheet. Bake for 10 minutes, until it reaches a temperature of 160F (71C). Remove from the oven and cool completely before adding to the frosting in step 17.
Meanwhile, measure out 1 cup (160g) of the roasted pineapple, finely chop it, and set it aside. Reserve any leftover pineapple to decorate the top of the cake or to snack on.
Add the butter to the bowl of a stand mixer fitted with the paddle attachment, and let ‘er rip on high until the butter is whipped and completely smooth, about 2 minutes, stopping to scrape down the sides of the bowl a couple times.
Add the confectioners’ sugar and cake mix. Start the mixer on low (to prevent a sugar explosion) and then gradually work up to high. Whip on high speed until the frosting is the lightest and fluffiest, about 2 minutes. Add the chopped pineapples, half-and-half, and vanilla, and mix on low to combine.
To decorate the cake, remove it from the fridge, invert it onto a large platter, and remove the parchment paper. Alternatively, just keep it in the pan. Use a pastry brush or spoon to soak the top of the cake with about 3 tablespoons of the liquid from the maraschino cherry jar.
Spread the frosting over the top of the soaked cake. Make it flat, or do swoops and swirls, whatever you feel. Decorate the top of the cake with the maraschino cherries, cut, and serve.

Serving Suggestions

The cake’s caramelized pineapple flavour pairs beautifully with coffee, tea, sparkling beverages, or tropical-inspired cocktails. For entertaining, prepare the cake ahead of time and decorate just before serving to create an impressive dessert presentation without last-minute stress.

Because of its vibrant appearance and nostalgic flavours, this cake is especially suited for celebrations where guests gather around the table. The combination of soft buttery cake, sweet roasted pineapple, and creamy frosting makes every slice feel festive and inviting.

Final Thoughts

This Pineapple Right-Side Up Cake Recipe is a celebration of tropical flavours, nostalgic desserts, and the joy of sharing food with others. Featured on Cook the Books Season 3: Celebrity Edition, hosted by Shahir Massoud, and inspired by Party People by Brie Larson and Courtney McBroom, this dessert transforms a familiar classic into a memorable celebration cake.

Find more recipes from Cook the Books here!