In a bowl, mix graham cracker crumbs, granulated sugar, and melted butter. Press into the bottom of a 9-inch springform pan. Chill in the fridge for 30 minutes.
In a mixing bowl, beat cream cheese until smooth. Add powdered sugar and vanilla extract, mix until well combined.
In a separate bowl, whip the heavy cream until stiff peaks form. Gently fold the whipped cream into the cream cheese mixture.
In a small saucepan, sprinkle gelatin over water and let it bloom for 5 minutes. Heat over low heat until the gelatin dissolves. Let it cool slightly.
Add crushed pineapple and pineapple juice to the cream cheese mixture. Pour in the gelatin mixture and mix well.
Pour the filling over the chilled crust. Smooth the top with a spatula. Chill in the fridge for at least 4 hours or overnight.
Before serving, run a knife around the edges of the cheesecake to loosen it from the pan. Remove the springform sides.
Slice and serve the pineapple cream cheesecake chilled. Enjoy!