Rinse and pat dry strawberries. Cut ¼ inch off the strawberries from the stem side and hollow out with a sharp knife.
In a small-medium bowl, melt chocolate chips in a microwave in 20 second intervals.
In a zip-loc bag, crushed Oreos using a roller.
Dip the tip of each strawberry into melted chocolate and then cookie crumbs. Place onto a wax paper-lined baking sheet.
In a medium bowl, mix together cream cheese, softened butter, vanilla, cocoa powder and sugar. Mix in remaining chocolate until incorporated and then whipped cream.
Using a pastry bag with a small fitting, pipe filling into each strawberry.
Serve immediately or refrigerate. Enjoy!