01 -
Preheat oven to 325°F (163°C). Grease a 9-inch springform pan. Sprinkle brown sugar evenly over the bottom. Arrange pineapple rings across the sugar and position a maraschino cherry in the center of each ring. Drizzle 1/4 cup melted butter over the fruit.
02 -
Stir graham cracker crumbs with remaining 1/4 cup melted butter until well combined. Evenly press crust mixture over the pineapple layer. Place pan in freezer for 10 to 15 minutes to set.
03 -
In a large mixing bowl, beat softened cream cheese with granulated sugar on medium speed until creamy and smooth, scraping sides as needed.
04 -
Add eggs to cream cheese mixture one at a time, mixing on low speed after each addition just until combined, without overbeating.
05 -
Blend in sour cream and vanilla extract until filling is fully combined and smooth.
06 -
Pour cheesecake batter evenly over the chilled crust and pineapple layer in pan. Gently smooth surface with a spatula.
07 -
Set springform pan into a larger roasting pan. Fill roasting pan with hot water halfway up the sides of the cheesecake pan. Bake for 60 to 70 minutes, until edges are set and center slightly jiggles.
08 -
Turn off oven and crack door open. Allow cheesecake to cool slowly in oven for 1 hour.
09 -
Remove from oven, cover, and refrigerate at least 4 hours or overnight until completely firm.
10 -
Run a thin knife around the edge of pan to loosen. Release springform, carefully invert cheesecake onto serving platter so pineapple layer is facing up, then slice and serve.