For The Topping:
- Cooking spray
- 4 tbsp. butter
- 1/2 c. packed brown sugar
- 1 (20-oz.) can pineapple rings in juice
- Stemless maraschino cherries
For The Cake:
- 1 box yellow cake mix
- 1/3 c. vegetable oil
- 1 c. pineapple juice
- 3 large eggs
For The Cheesecake:
- 3 (8-oz.) blocks cream cheese, softened
- 1 c. granulated sugar
- 3 large eggs
- 1/4 c. sour cream
- 2 tsp. pure vanilla extract
- 1/2 tsp. kosher salt
1 Make topping: Preheat oven to 350° and grease a 8″ springform pan with cooking spray. In an 8″ cake pan, melt butter in oven. Add brown sugar to the bottom of the regular cake pan. Spread mixture to the edges, then add 5 pineapple rings. Place cherries inside and in between pineapple slices.
2 Make cake: In a large bowl, combine cake mix, oil, pineapple juice and eggs. Whisk until smooth, then pour about half the mixture over the pineapples in the regular cake pan. Pour remaining half into the springform pan. Bake until cakes are starting to turn golden and a toothpick inserted into the centers comes out clean, about 20 minutes (the regular cake pan might take an additional 10 to 15 minutes). Let cool.
3 Meanwhile, make cheesecake layer: In a large bowl, beat cream cheese with a hand mixer until light and fluffy. Add sugar and beat until smooth. Add eggs one at a time, beating between each addition. Add sour cream, vanilla, and salt and mix until smooth. Pour cheesecake layer over the cooled baked cake in the springform pan. Wrap the bottom of the springform pan in foil.
4 Bake until cheesecake is slightly jiggly in the center, 1 hour to 1 hour 10 minutes. (Cheesecakes tend to crack if you don’t use a water bath. If you don’t want to use one, bake as directed. If you do want to use a water bath, double wrap the outside of the pan in aluminum foil and place in a baking dish. Place on oven rack and pour into baking dish enough boiling water to reach halfway up, taking care not to splash water into the cheesecake. Bake as directed.)
5 If not using a water bath: Remove pan from oven and run a knife around the inside of the pan to release the cheesecake. Let cool 1 hour on a wire rack, then refrigerate until totally chilled, at least 4 hours and up to overnight. If using a water bath: Turn off oven heat, prop open oven door, and let cheesecake cool in oven, 1 hour. Transfer to refrigerator and cool completely, 4 hours up to overnight.
6 Place cheesecake on a serving plate and top with pineapple upside-down cake.