There haven't been too many chocolate desserts on this site. I feel like we need to issue an apology! Chocolate is life. It's indulgent and comforting, decadent and delightful. These chocolatey Halloween treats are tasty and frightful. Ok, maybe not frightful but we can pretend. When I was writing Halloween recipes, believe it or not, my goal was ease. Now, I might not have accomplished that entirely with the hand pies but if you took the face carving part out, they're a success! Well these guys make up for that. They're super easy to whip up and are more assembly than anything.
Introducing Tombstone Cups. Pudding, Oreo cookies, whipped cream and Double Chocolate Milano cookies. A couple things before you get started. Instant pudding is your best friend. It whips up quick on the stove and who doesn't love chocolate pudding? I used traditional Oreo cookies but any sandwich cookie, vanilla or chocolate, works for this. If you can find green ones, those might be fun to include instead. Put several in a seal-able bag, bang it around on the counter a couple of times to break them up and call it a day. The whipped cream I used is heavy whipping cream I whipped myself. I didn't sweeten it since these cups are plenty sweet themselves but if you want to add something, add about a tablespoon or two of powdered sugar as you whip it. With all the store-bought ingredients included in this recipe, I wanted to control the sugar factor in at least of them. Finally, Milano sandwich cookies are my personal favorite store-bought cookie in the entire world. That reason alone is the why I chose them. You can use any oval or rectangular cookies though. It's up to you.
Assembly is simple. Start with one layer of crushed cookies to cover the bottom. Spoon a layer of pudding, top with another layer of cookies, one more layer of pudding, cookies, whipped cream and more cookies. Before adding the Milano or whichever cookie you choose, write RIP towards the top. Chocolate frosting would be much easier to handle but I forgot to grab that at the store (and I wasn't making it myself). So instead, I used a tiny bit of chocolate syrup and applied the letters with a toothpick. Talk about resourcefulness, that should get ten points right there. You can buy frosting in tubes, that is what I'd recommend for an easy application. Finally, nestle the cookie towards the back of the cup so that it looks like a burial site.
If you wanted to spook these up a little more, you could add gummy worms and candy spiders in the crushed cookie layers. Maybe even have a few coming out over the edge of the cup. Clear plastic cups are ideal, about 8 ounces or so. I recommend eating these with a glass of milk handy. As delicious as they are, they are also incredibly rich. They are also fantastic to prepare ahead. Assemble them the night before a party, place them on a platter and store in the fridge until your guests are about to arrive.
2 packages of Chocolate Pudding (I used Jell-O)
12 sandwich cookies (I used Oreo), crushed
1/2 cup of Heavy Whipping Cream
8 Milano Cookies
Chocolate Frosting In A Tube or Chocolate Syrup
1. Prepare the chocolate pudding according to package instructions. Using a mixer, whup the heavy whipping cream until it's thick and fluffy. Set aside.
2. Begin layering your cups. Start with a layer of crushed sandwich cookies followed by pudding, another layer of cookies, pudding, cookies again followed by a scoop of the whipped cream. Sprinkle the top with more crushed cookies.
3. Squeeze the letters RIP onto the Milano cookies using the frosting in a tube. If you don't have frosting, using a toothpick, carefully write the letters by carving chocolate syrup onto the cookies. Nestle the cookie towards the back of the cup careful not to drag too much whipped cream down with it. Serve!
Makes 8 cups