Trim stems off the strawberries, then depending on the size, for small to medium, cut each in half, and for large berries, cut into quarters (lengthwise). Place in a mixing bowl.
Add the granulated sugar to the strawberries and gently mix together. This will juice the strawberries. Place bowl in the fridge for an hour.
In another mixing bowl, beat together the cream cheese, powdered sugar, Dream Whip, and vanilla extract.
Pour mixture into the pie crust and spread out evenly. Place in the fridge.
Place a strainer on another bowl and drain the strawberries, reserving the juice. Measure out 1/2 cup of that juice and set that and the strawberries aside. (For the remaining strawberry juice, save that and pour over angel food cake another day.)
Another mixing bowl, dissolve the gelatin in the boiling water, stir in that 1/2 cup of reserved strawberry juice, then add the strawberries and stir together. Place in the fridge until set and cooled.
Mix the strawberry gelatin and pour over the cream cheese mixture in the pie crust. Place in the fridge until ready to serve.