In a large bowl, add the instant pudding, sweetened condensed milk, and milk. Whisk until combined and the pudding mixture is smooth. Place the bowl in the fridge to chill.
Using a stand or hand mixer, whip the heavy whipping cream on medium speed until stiff peaks form, about 3-4 minutes. Grab the bowl of pudding from the refrigerator. Gently fold the whipped cream completely into the pudding. Place the bowl back in the fridge to chill for another 15 minutes. Add the Oreo cookies to a food processor. Blend until the cookies become a fine crumb, about 15-20 seconds.
To assemble, sprinkle a heaping spoonful of cookie crumbs into the bottom of a jar or cup. Next, add a few spoonfuls of the pudding to the cup/jar and smooth into an even layer. Repeat the process again, adding another layer of cookie crumbs and another layer of pudding. Top the second pudding layer with more cookie crumbs. Enjoy!
Optional: You can enjoy the dirt cups as is, or jazz them up for Easter! You can top them with things like green colored coconut, marshmallow bunnies, and candy eggs to make them festive.