Crush the Oreos in a zip-top bag using a rolling pin or a food processor until they resemble fine crumbs.

In a large mixing bowl, combine softened cream cheese, powdered sugar, whipped cream, and vanilla extract. Mix until smooth and creamy.

Gently fold the crushed Oreo cookies into the cream cheese mixture until combined.

Form the Oreo cheesecake mixture into small balls, about 1 inch in diameter, and place them on a parchment-lined baking sheet.

Chill the formed bites in the refrigerator for at least 3 hours or until firm.

If desired, melt the dipping chocolate and dip each chilled bite until fully coated. Return to the parchment-lined baking sheet.

Allow the chocolate to harden at room temperature or in the fridge before serving.