Here it is — a show-stopping Pineapple Upside-Down Cheesecake!
This dessert layers classic caramelized pineapple topping over a rich, creamy cheesecake with a buttery cake-like or graham crust. Stunning AND delicious.

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🍍🔥 Pineapple Upside-Down Cheesecake

Ingredients

Pineapple Topping

• ¼ cup butter
• ½ cup brown sugar
• Pineapple slices (fresh or canned, drained)
• Maraschino cherries

Crust

(Choose one)

• Graham crust:
  • 1½ cups graham cracker crumbs
  • ¼ cup sugar
  • 6 tbsp melted butter
• Cake layer (more traditional to the upside-down dessert):
  • 1 box yellow cake mix (you’ll only use ~½)
  • ¼ cup melted butter
  • 1 egg

Cheesecake Filling

• 24 oz (3 packages) cream cheese, softened
• 1 cup sugar
• 3 large eggs
• 1 cup sour cream
• 1 tbsp vanilla extract
• 1 tbsp lemon juice
• Pinch of salt

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🧁 Instructions

1. Prepare the Pineapple Topping

1. Preheat oven to 325°F (160°C).
2. Melt butter and brown sugar in a small saucepan until bubbly.
3. Pour into the bottom of a 9-inch springform pan lined with parchment on the bottom.
4. Arrange pineapple rings over the caramel.
5. Add cherries in the centers.

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Option A: Graham Crust

1. Combine crumbs, sugar, and melted butter.
2. Press gently over and around pineapple slices—don’t disturb the design.
3. Freeze while preparing filling.

Option B: Pineapple Cake Layer (Dense & Classic)

1. Mix half the cake mix with butter and egg.
2. Spread gently over pineapple.
3. Bake 12–15 minutes until just set.
4. Cool for 10 minutes.

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2. Make the Cheesecake Filling

1. Beat cream cheese until smooth.
2. Add sugar and mix until creamy.
3. Add eggs one at a time on low speed.
4. Mix in sour cream, vanilla, lemon juice, and salt—just until combined.

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3. Assemble & Bake

1. Pour cheesecake filling over crust/topping.
2. Wrap the outside of the pan tightly in foil.
3. Place into a roasting pan and fill with hot water halfway up the sides (water bath).
4. Bake 60–75 minutes until the center has a slight wobble.

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4. Cool

1. Turn off oven, crack door, and let cheesecake sit 1 hour.
2. Cool completely on the counter.
3. Refrigerate at least 6 hours (overnight best).

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5. Flip It!

1. Run a knife around the edge of the pan.
2. Unlatch springform ring and invert cheesecake onto a large plate.
3. Peel off parchment.
4. The caramelized pineapple should be glossy and beautiful.

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✨ Optional Add-Ins

Pineapple Boost

• Fold ½ cup crushed pineapple (well drained) into the cheesecake batter.

Coconut Twist

• Add ½ cup shredded coconut to crust
• Or top the cheesecake with toasted coconut after flipping.

Tropical Touch

• Add 1 tsp rum extract to the filling.

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🍽️ Serving Tips

• Slice with a hot knife wiped between cuts.
• Serve with whipped cream or vanilla ice cream.

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If you want, I can also give you:
🍍 A no-bake pineapple upside-down cheesecake
🍍 A mini cheesecake cupcake version
🍍 A Pineapple Coconut Upside-Down Cheesecake

Just tell me!