In a large bowl, beat the softened cream cheese, vanilla and sugar until light and fluffy. Use a hand mixer on low or a stand mixer with a paddle. Take your time and incorporate the sugar well.
Fold in the drained, crushed pineapple and cool whip.
Spoon the pineapple cream cheese mixture into the premade pie crust.
Refrigerate for at least 4 hours, preferably overnight.