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Preheat the oven to 350 degrees F (175 degrees C).
Make the crust: Combine cookie crumbs, brown sugar, melted butter, and cinnamon in a medium bowl; firmly press mixture evenly onto the bottom and 1 inch up the sides of a 10-inch springform pan. Bake in the preheated oven for 5 minutes; set aside.
Prepare the cheesecake: Beat cream cheese in a large bowl until smooth. Gradually mix in 1 ¼ cups sugar, heavy whipping cream, flour, and 1 teaspoon vanilla. Beat in eggs, one at a time, beating after each addition. Pour ⅓ of the batter into the prepared pan. Top with cookie pieces; pour in remaining batter.
Bake in the preheated oven for 45 minutes. Remove cake from the oven.
Combine sour cream, remaining ¼ cup sugar, and remaining 1 teaspoon vanilla; spread evenly on cheesecake. Continue baking for 7 minutes. Turn oven off, leaving cheesecake in for an additional 30 minutes. Remove cheesecake and let cool completely on a wire rack.
Make the chocolate topping: Combine chocolate chips and heavy whipping cream in a saucepan; stir over low heat until chocolate melts, then stir in vanilla. Pour mixture over cheesecake while still warm.
Refrigerate before serving, at least 8 hours or overnight. Remove about ½ hour to 1 hour before serving and remove the ring from the springform pan.