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Using a food processor (or Ziploc bag + rolling pin or meat tenderizer), crush the Oreo cookies into crumbles, then set aside.
Place chopped semi-sweet chocolate in a small bowl. Heat milk until steaming, then pour over chocolate. Let sit for 2-3 minutes, then stir. If any chunks of chocolate remain, heat in microwave for 30-second intervals until all chocolate has melted. Mixture will be very liquid, like chocolate milk. Set aside and let cool to room temperature.
Using a stand mixer (or hand mixer + large bowl), add in chilled heavy cream, Baileys, and powdered sugar and beat on high speed until stiff peaks form, about 5-7 minutes.
Divide cream mixture in half. First half of whipped cream will be left alone and is ready to use in parfait. Second half will be mixed with chocolate. When ready, slowly add chocolate mixture over this half of whipped cream, gently (yet thoroughly) folding them together until completely mixed.
To assemble parfaits: Using a pastry bag (or just a spoon), add layers of cream and crushed cookies as you see fit. To do this as pictured, I layered chocolate, then cream, then cookies, then cream again, then chocolate again, then cream again, and finally finish with any remaining cookie crumbles on top.
Serve as desired. If you'd like chocolate layer to be firmer, chill parfaits for 2-3 hours before serving.