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.