Upside Down Strawberry Shortcake Cheesecake

Upside Down Strawberry Shortcake Cheesecake

Serves: 8 people
Prep Time: 20 minutes
Cooking Time: 20 minutes
Upside Down Strawberry Shortcake Cheesecake
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  • 2 (8 oz.) packages cream cheese, room temperature
  • 1 1/2 cups brown sugar
  • 2/3 cup sugar
  • 1/4 cup whole milk
  • 2 teaspoons vanilla extract
  • 1 (16 oz.) container frozen whipped topping, thawed
  • 3 pints strawberries, thinly sliced
  • 30 golden/vanilla sandwich cookies
  • 1 cup milk


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Anyone who’s read a sampling of our recipes know that we’ve got a sweet tooth about as big as the Grand Canyon over here and that we’re constantly on the hunt for delicious desserts - especially ones that looks as good as they taste. Whether it’s a tiered cake, a mousse confection or a fruity pie, we’re always up for that last (and best) course. Recently though we were looking to step outside our comfort zone a bit and make something that, though it required a bit more patience, took our breath away when we saw the finished result. Addictively delicious and absolutely stunning, this is how we made our upside down strawberry shortcake cheesecake.  Alrighty, so this dessert’s name is a bit of a mouthful, but it’s got a lot going on! The strawberries! The ice box cake element, the cheesecake filling, the fact that it is in fact upside down. All of these components come together to create one incredible dessert that we were proud to make and serve our loved ones. Before you get started on yours, we’ll walk you through the process of how this gorgeous show-stopper comes together. You’ll line a bowl with plastic wrap - to make the inverting of the whole thing easier at the end - then start layering your strawberries. Try to overlap them a bit, but if they slide around a little, it’s no problem. Also, we went with a slightly smaller bowl, since we decided to make this dessert for date night, but if you’re serving a crowd you can go bigger. Then you make your cream cheese filling and get to layering. We dolloped some of our filling into the bottom of our bowl and spread it into an even layer, then spread more strawberry slices out on top of the filling. Dunk a couple golden oreos into a cup of milk, then layer them over the strawberries. Repeat that process as many times as necessary until you fill your bowl, making sure to end with a layer of cookies. Wrap that bad boy in plastic wrap and then you’re good to go! The whole thing sets in the fridge and when you’re ready to serve it, you flip it onto a serving platter and serve your masterpiece.
  1. In a large bowl, beat together cream cheese, brown sugar and regular sugar for 4-5 minutes, or until smooth and creamy.
  2. Add milk and vanilla extract and beat to combine.
  3. Fold in frozen whipped topping until fully incorporated.
  4. Place a large sheet of plastic wrap in a medium bowl, making sure to line the whole bowl while creating as smooth a layer as possible. Take strawberry slices and line the bowl completely with them.
  5. Spoon 1 cup cream cheese mixture into strawberry bowl and spread into an even layer.
  6. Optional: make a layer of strawberry slices over cream mixture.
  7. Dip sandwich cookies into 1 cup milk, then make a layer of cookies on top of the strawberries.
  8. Repeat until all strawberries and cream mixture are used, then top with one final layer of milk-dipped sandwich cookies.
  9. Wrap tightly in plastic wrap and refrigerate until set. 2-4 hours.
  10. Remove from fridge and turn out onto serving platter, then remove plastic wrap and slice, serve and enjoy!