Reserve 8 whole Oreos and 8 whole chocolate chip cookies for garnish. Place the remaining cookies into two separate Ziploc bags and crush them into coarse pieces.

In a chilled bowl, whip the heavy cream until stiff peaks form. Set aside in the refrigerator.

In a large bowl, beat the softened cream cheese until completely smooth and creamy, about 3 minutes.

Add the powdered sugar and vanilla extract to the cream cheese and beat until fully combined.

Gently fold the chilled whipped cream into the cream cheese mixture until no white streaks remain. Do not overmix.

Divide the cheesecake batter evenly into two bowls. Leave one white, and add royal blue gel food coloring to the other, mixing until brightly colored.

Transfer the blue batter into one piping bag and the white batter into a second piping bag.

Pipe a layer of blue cheesecake into the bottom of each plastic cup.

Add a layer of crushed chocolate chip cookies, followed by a layer of white cheesecake, then a layer of crushed Oreos.

Repeat the layering process until the cups are full, ending with a swirl of cheesecake on top.

Garnish each cup with half of a reserved Oreo and half of a chocolate chip cookie.

Secure dome lids on the cups and refrigerate for at least 4 hours before serving to allow the dessert to set.