Wash and slice the stems from 25 large strawberries or 35 medium strawberries. Pull the top off of the strawberry. Using a paring knife or a small spoon, clean out the hull of the strawberry. Slice a tiny bit of strawberry off the bottom so that you have a stable base.
Set the strawberries on a paper towel to drain out any extra juices. Set aside.
In a large bowl using a hand mixer or in the bowl of a stand mixer, combine cream cheese, powdered sugar, sour cream, and vanilla extract. Mix until smooth.
Spoon the cream cheese mixture into a large zip bag and cut a small hole on the corner, or use a piping bag. You can use a cute piping tip to make the strawberry filling a little fancier.
Pipe the cream cheese mixture into the hole of each strawberry and set them on a baking sheet lined with parchment paper, serving dish, or plate.
Garnish each strawberry with mini chocolate chips and small pieces of graham cracker or even a little glob of cool whip.