Step 1

Dice half of the pineapple into small pieces, and set aside at least 4 rings for the top of the pie.

Step 2

Beat cream cheese with a mixer until softened.

Step 3

Add pineapple juice and mix until lumps are mostly gone.

Step 4

Fold in sweetened condensed milk and beat until fluffy.

Step 5

Mix in diced pineapple.

Step 6

Store filling in refrigerator while making the crust and whipped cream.

Step 7

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.

Step 8

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.

Step 9

Pour pineapple filling into crust. Refrigerate for at least 2 hours. Alternatively, you can freeze this pie for a frozen icebox treat.

Step 10

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.