In a large mixing bowl, add the softened cream cheese and granulated sugar. Using a hand mixer or stand mixer, beat on medium-high speed until the mixture is smooth, creamy, and free of lumps.
Add the thawed Cool Whip to the cream cheese mixture. Gently fold it in using a spatula until fully combined and light in texture. Avoid overmixing to keep the filling fluffy.
Make sure the crushed pineapple is very well drained to prevent the cheesecake from becoming too soft. Add the pineapple to the mixture and stir gently until evenly incorporated.
Spoon the cheesecake filling into the prepared graham cracker crust. Spread it out evenly using a spatula, smoothing the top.
Place the cheesecake in the refrigerator for at least 4 hours, or until fully set. For a firmer texture and faster setting, you can place it in the freezer for about 1–2 hours, then transfer it to the fridge.
Once set, remove the cheesecake from the refrigerator.
Garnish with whipped cream and maraschino cherries if desired.
Slice and serve chilled.
Enjoy!
