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.
Notes
To make things easy, purchase a cored pineapple at the grocery store in the deli section. It will have enough juice in the bottom of the container to make this pie.
Pineapple pie can be frozen instead of refrigerated if you'd like an icebox pie. Freeze before decorating. To serve, allow to sit at room temperature at least 10 minutes, decorate and slice.
Store leftovers in the refrigerator in an airtight container for up to 5 days.
You can freeze this pie for later...or enjoy it frozen! Wrap it well in plastic wrap or aluminum foil, then freeze for up to 3 months. To serve it frozen, let it thaw for about 10 minutes at room temperature, then cut and serve.