Preheat your oven to 350 degrees F. Melt 1 stick, ½ cup, butter and divide evenly between two 9-inch cake pans.
Sprinkle about ¼ cup of brown sugar into the bottom of each cake pan in an even layer.
Layer half of the pineapple rings into the bottom of each cake pan in an even layer. Place a cherry in the center of each pineapple ring and anywhere else you see an empty spot. I used about 10 for each cake.
In the bowl of a stand mixer equipped with a paddle attachment, cream the remaining 1 cup of butter and sugar on med-high speed until light and fluffy.
Add the eggs and vanilla extract and mix until combined. Scrape the sides and bottom of the bowl.
Add in the sour cream and reserved pineapple juice and mix until combined.
Add the flour, salt, baking powder, and baking soda and mix until there are no dry spots remaining.
Scrape the sides and bottom of the bowl to make sure all the ingredients are well incorporated.
Divide the batter evenly between the two cake pans and smooth the batter evenly over the pineapple/cherry layer.
Bake for 30-35 minutes or until a toothpick inserted in the center of each cake comes out clean.
Remove the cakes from the oven when they are done and allow to cool completely on a wire rack.
When the cakes are cool, prepare the cheesecake filling by adding the cream cheese into the bowl of a stand mixer equipped with a paddle attachment and cream until smooth.
Add the powdered sugar and vanilla extract and mix until well combined.
Slowly pour in the heavy whipping cream with the mixer on low speed. Slowly increase the speed to high for 1-2 minutes.
In the bottom of a 9-inch springform pan, add a sheet of parchment paper. Flip one of the cakes over and place pineapple side up in the bottom of the pan. Top the cake with the cream cheese mixture and smooth.
Place the other cake layer on top and gently press into the cheesecake layer.
Place the springform pan into the freezer for at least 2 hours or until the cheesecake layer is set, or in the refrigerator overnight.
Remove the cheesecake from the freezer or refrigerator and carefully run hot water or a kitchen torch around the side of the springform to loosen the form and release the cake.
Transfer to a cake plate or stand to serve.
Store in an airtight container in the refrigerator for up to three days.