Crush approximately 20 Oreo cookies in a food processor or in a plastic bag with a rolling pin until fine crumbs. Set aside in a bowl.

In a mixing bowl, beat 8 ounces of softened cream cheese until smooth, about 2-3 minutes. Gradually add 1 cup powdered sugar and 4 ounces melted chocolate, mixing until combined. Fold in ½ cup Baileys until no streaks remain.

In a separate bowl, whip 1 cup heavy cream until soft peaks form, then gradually add 2 tablespoons powdered sugar and 1 teaspoon vanilla extract. Whip until stiff peaks are reached.

Layer crushed Oreo mixture, cheesecake mixture, and whipped cream in clear cups or a trifle dish. Repeat layers and finish with whipped cream.

Cover with plastic wrap and chill for at least 2 hours to set flavors.

Add optional garnishes like extra whipped cream, Oreo crumbs, or shaved chocolate before serving.