Make the cookie crumb base: Crush the chocolate cookies in a food processor or in a zip-top bag with a rolling pin. Stir in melted butter and a pinch of salt until the mixture resembles damp sand.
Press into cups: Spoon 1–2 tablespoons of crumbs into the bottom of each dessert cup or small jar.
Lightly press to create a base. Set aside. Reserve a handful of crumbs for topping if you like.
Whip the cream: In a cold bowl, whisk the heavy cream to medium-stiff peaks.
Do not overwhip. Set aside.
Beat the cheesecake mixture: In a separate bowl, beat the softened cream cheese with powdered sugar and vanilla until smooth and fluffy. Add Baileys gradually, tasting as you go.
Aim for a smooth, spreadable texture.
Fold it together: Gently fold the whipped cream into the Baileys cheesecake mixture in two additions until fully combined and airy.
Make the chocolate ganache: Heat the milk or cream just to a simmer. Pour over the chopped dark chocolate and let sit for 1 minute. Stir until glossy and smooth.
Let cool to room temp so it thickens slightly.
Layer it up: Add a layer of cheesecake filling over the cookie base, then drizzle or spoon a thin layer of ganache. Repeat with another layer of cheesecake. Finish with a final drizzle of ganache.
Chill: Cover and refrigerate for at least 2 hours, or up to 24 hours.
This helps the layers set and the flavors meld.
Garnish and serve: Top with chocolate shavings, a pinch of reserved cookie crumbs, or a light dusting of cocoa. Serve cold.