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I stumbled across this recipe last summer when trying to combine my husband's love of cheesecake with my grandmother's famous pineapple upside-down cake. This dessert quickly became our family's special occasion showstopper. The combination of buttery, caramelized pineapple cake layers sandwiching a creamy vanilla cheesecake creates this incredible flavor marriage that makes people think you spent days in the kitchen.
Last month, I brought this to my friend's luau-themed birthday party. Her normally reserved father-in-law ate two slices and then asked if I made it professionally. Sometimes the most unexpected combinations make the biggest impression!
Key Ingredients
- Pineapple rings - Fresh pineapple works beautifully but canned rings provide that classic look and consistent thickness. Pat them dry before using to prevent excess moisture.
- Maraschino cherries - These add that pop of color and nostalgic touch. Make sure to drain and dry them thoroughly.
- Brown sugar - Creates that signature caramelized topping when combined with butter. Dark brown sugar gives a deeper molasses flavor.
- Sour cream - Appears in both the cake and cheesecake, adding moisture to the cake and tanginess to the cheesecake. Full-fat works best for the richest flavor.
- Pineapple juice - Infuses the cake layers with tropical flavor. Reserved juice from the canned pineapple works perfectly.
- Cream cheese - Use full-fat, brick-style cream cheese for the best texture. Allow it to fully soften for a smooth, lump-free cheesecake.
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Baking Instructions
- Create perfect pineapple layers:
- Arrange your pineapple rings and cherries carefully in the prepared pans. Pour the brown sugar-butter mixture evenly beneath them. This becomes the beautiful top once inverted. When pouring the batter over the fruit, do so gently to avoid displacing your arrangement.
- Master the cake texture:
- Cream the butter and sugar until genuinely light and fluffy - at least 3-4 minutes. This creates the foundation for a tender cake. When adding dry ingredients, mix just until combined to prevent toughness.
- Perfect the cheesecake:
- Beat room temperature cream cheese until completely smooth before adding other ingredients. This prevents lumps that are impossible to remove later. The water bath, while an extra step, ensures gentle, even baking without cracks.
- Cool strategically:
- Allow the upside-down cakes to cool in their pans for exactly 10 minutes before inverting. Too soon and they fall apart; too late and the caramel hardens, sticking to the pan. For the cheesecake, the gradual cooling in the turned-off oven prevents cracking.
- Assemble with care:
- Make sure all components are completely cooled before assembly. Place the bottom cake layer caramelized-side up on your serving plate. Gently position the cheesecake layer, then top with the second cake, caramelized-side up again.
- Chill before serving:
- Once assembled, refrigerate for at least an hour to allow the layers to set together. This makes cleaner slices and helps the flavors meld beautifully.
First time I made this, I tried to rush the cooling process for the cheesecake and it cracked dramatically. Now I'm religious about that slow cool-down in the oven with the door cracked. I've also learned that thoroughly greasing the cake pans and lining the bottoms with parchment paper makes a huge difference in how cleanly the cakes release. My latest improvement was adding a tiny pinch of salt to the caramel mixture, which really enhances the flavor without making it taste salty.
Serving Suggestions
Present this stunning dessert on a pedestal cake stand to showcase all those beautiful layers. The height gives it presence on any dessert table. For summer gatherings, serve with a small scoop of coconut ice cream or a dollop of rum-spiked whipped cream for an extra-tropical touch. The cold cream with the room temperature cake creates an amazing contrast. A sprig of mint adds a touch of freshness to each plate. For brunch settings, a side of fresh berries balances the sweetness beautifully.
Creative Variations
Try using rings of different tropical fruits like mango or peach between the pineapple for a colorful twist. For a coconut lover's version, add 1/2 cup toasted coconut to the cake batter and garnish the sides with toasted coconut flakes. A tablespoon of rum or coconut rum in both the cake batter and cheesecake adds a sophisticated flavor for adult gatherings. During the holidays, add a pinch of cinnamon and clove to the caramel mixture for a warm, spiced version that still maintains its tropical essence.
Storage Solutions
This cheesecake keeps beautifully in the refrigerator for up to 5 days. Store in a cake keeper or loosely tent with foil to protect the surface without smudging the presentation. Individual slices can be wrapped and frozen for up to a month - thaw overnight in the refrigerator for best texture. If making ahead for a party, prepare all components separately, refrigerate, and assemble within 24 hours of serving for the freshest presentation. Let it sit at room temperature for 20-30 minutes before serving for the best flavor.
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I've made this pineapple upside-down cheesecake for countless summer gatherings, holiday dinners, and even as an unconventional birthday cake. There's something magical about the combination of warm, caramelized pineapple flavors, buttery cake, and creamy cheesecake that seems to appeal to everyone. While it takes some time to prepare all the components, the make-ahead nature makes it manageable, and the "wow" factor when you present it makes every minute worthwhile!
Frequently Asked Questions
- → Can I make this dessert ahead of time?
- Yes! This dessert is actually perfect for making ahead. You can prepare all components 1-2 days in advance and store separately in the refrigerator. Assemble just before serving or up to 24 hours ahead and refrigerate until ready to serve.
- → Can I use canned pineapple juice for this recipe?
- Absolutely! The juice from your can of pineapple rings works perfectly. If you don't have enough, you can supplement with store-bought pineapple juice or even substitute orange juice in a pinch.
- → What's the best way to cut and serve this cake?
- For clean slices, use a sharp knife dipped in hot water and wiped dry between cuts. Let the cake sit at room temperature for about 20 minutes before slicing to allow the cheesecake layer to soften slightly.
- → Can I freeze this cheesecake?
- Yes, you can freeze the assembled cake for up to 1 month. Wrap it tightly in plastic wrap and then aluminum foil. Thaw overnight in the refrigerator before serving. The texture of the pineapple cake may change slightly, but it will still be delicious.
- → What if I don't have a springform pan?
- You can use a regular 9-inch cake pan for the cheesecake layer, but line it with parchment paper with overhang on the sides to help lift it out after chilling. Alternatively, you can make the cheesecake in a pie dish and carefully transfer it to the cake after it's fully set.