- 2 1/2 sticks butter, divided, at room temperature
- 1/2 cup dark brown sugar
- 1 (14-ounce) can pineapple rings, drained with 1/8 cup of juice reserved
- 20 maraschino cherries, drained
- 3/4 cup sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 1 1/2 cups all-purpose flour
- 1 teaspoon salt
- 1/4 teaspoon baking soda
- 1/2 teaspoon baking powder
- 1/2 cup sour cream
- 2 cups cream cheese, softened at room temperature
- 1 (14-ounce) can sweetened condensed milk
- Zest and juice of 1 lemon
- 2 teaspoons vanilla extract
- Make the pineapple upside down cake: Preheat the oven to 350 degrees, and line two 9-inch pans with parchment and baking spray.
- In a small bowl, cream one stick of butter with brown sugar.
- Divide between prepared pans and spread to form an even layer in the pan.
- Place pineapple rings on top of the brown sugar mixture and place cherries inside of the rings and to fill the spaces in between the rings.
- Set aside.
- In a large bowl, cream remaining butter with sugar.
- Add eggs one at a time and then the vanilla.
- Stir in flour, salt, baking powder and baking soda until combined.
- Fold in sour cream and pineapple juice and divide batter between prepared pans.
- Bake for 30 to 35 minutes until cake is golden and a toothpick comes out clean.
- Allow to cool 15 minutes and then flip out onto a cooling rack, taking care to keep pineapple and cherries intact.
- For the cheesecake filling: In a large bowl, beat cream cheese until smooth.
- Stir in sweetened condensed milk, lemon zest and juice and vanilla.
- Place on bottom half of the cooled pineapple.
- Place in the freezer and allow to set for up to 1 hour.
- Remove cake from freezer and top with remaining layer of pineapple upside down cake.
- Cake will keep up to 3 days covered in the refrigerator.