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Dice half of the pineapple into small pieces, and set aside at least 4 rings for the top of the pie.
Beat cream cheese with a mixer until softened.
Add pineapple juice and mix until lumps are mostly gone.
Fold in sweetened condensed milk and beat until fluffy.
Mix in diced pineapple.
Store filling in refrigerator while making the crust and whipped cream.
Pour heavy whipping cream into a mixer and beat for at least 2 minutes on high until peaks form. Add powdered sugar and vanilla. Beat until fluffy. Refrigerate until ready to use.
Mix graham cracker crumbs with melted butter in a separate bowl. Press into the bottom and up the sides of a 9 inch deep dish pie plate.
Pour pineapple filling into crust. Refrigerate for at least 2 hours. Alternatively, you can freeze this pie for a frozen icebox treat.
After pie has cooled, place 4 pineapple rings in the middle of the pie, then decorate with piped whipped cream and place cherries on top if desired.