In a medium mixing bowl, beat cream cheese, powdered sugar, cocoa powder, 1 teaspoon vanilla extract, and sea salt together until combined.
Add ¼ cup Baileys and continue beating until smooth and fluffy.
In a separate mixing bowl, beat 1 cup of heavy whipping cream until it doubles in volume and begins to thicken.
Add in 2 tablespoons Baileys, 1 teaspoon of vanilla extract, 2 tablespoons of cocoa powder, and 2 tablespoons powdered sugar.
Beat until the mixture is nice and thick and stiff peaks form.
Place Oreo cookies into a gallon size plastic bag and crush with a rolling pin to form small crumbles.
Spoon the cheesecake mixture and whipped cream mixture each into a large piping bag.
Beginning with the cookie crumbs, layer cookie crumbs, cheesecake mixture, and whipped cream mixture into four lowball glasses. Repeat with a second layer of cookie crumbs and cheesecake mixture.
Put an open star piping tip (e.g., Tip #1M) on the whipped cream piping bag and pipe a swirl on the top of each glass.
Serve with a sprinkle of crushed cookies on top.
Notes
Since these desserts are quite thick, you don’t need to chill them before serving although if you are making them a day in advance then please do cover them and store in the refrigerator!
Powdered sugar has been used in this recipe since it blends in so well with the smooth cheesecake and whipped cream layers.
You could use a spoon to add the different layers of the dessert to each glass container although I find that piping the layers results in better uniformity and less mess! If you don't have piping bags and tips, a Ziploc bag with the corner snipped off will do the trick!
If you are catering to a larger crowd, instead of making more dessert, simply use smaller glass containers or bowls to give 6 servings instead of the 4 generous servings. Trust me, you’ll still have plenty of dessert per serving if you divide it further this way. You could even use small clear plastic cups - think Dixie cup size - and make a bunch of mini desserts as part of a larger dessert table spread.