In a large bowl, whisk milk, Baileys, and pudding mix until well combined. Let pudding thicken 5 minutes.
Spread half of pudding into prepared crust in an even layer. Top with Oreo crumbs and chips. Gently spread remaining pudding over.
Cover pan with a layer of plastic wrap to prevent it from forming a skin. Refrigerate at least 8 hours or up to overnight.
In a large bowl, using a handheld mixer or a stand mixer fitted with the whisk attachment, whip cream until soft peaks form, about 2 minutes.
Add granulated sugar and Baileys and whip until mixture is thickened and creamy, about 1 minute (it should hold its shape when you lift the mixer up).
Dollop cream onto pie (be sure to use all of it). Top with desired toppings (if using).
