Chocolate Cherry Upside Down Cake

With its gooey cherry topping and rich chocolate base, this Chocolate Cherry Upside Down Cake is my go-to when I need an easy crowd-pleaser that still feels special. Sweet and tart cherries meld perfectly into the pillow-soft cake while the buttery brown sugar layer turns decadent in the oven. Serve it at a party or for a weeknight treat—everyone will ask for seconds.

I remember making this for my mom’s birthday because it was her favorite flavor combo and now baking it always reminds me of laughter and second helpings around the table.

Ingredients

• Cherry pie filling: brings both sweetness and a burst of tang use a quality brand for the best fruit texture
• Unsalted butter: adds richness and helps create that caramelized gooey layer look for butter that’s pale yellow for fresher flavor
• Brown sugar: deepens the caramel notes opt for dark brown if you want a richer taste
• Chocolate cake mix: makes things simple but delivers a super moist crumb choose your favorite brand or one with cocoa as the first ingredient
• Large eggs: bind everything together and add moisture fresher eggs give the most lift
• Vegetable oil: keeps the cake tender and extra soft go for neutral oil to let the chocolate shine
• Water: helps the batter come together use filtered water if possible to keep flavors clean
• Vanilla extract: rounds out the chocolatey taste try to use pure extract for a more real flavor

Step-by-Step Instructions

Prepare the Topping:

Grease a 9 by 13 inch baking pan with butter or a nonstick spray then pour melted butter evenly across the bottom making sure to cover every corner Next sprinkle the brown sugar over the butter spreading it out in an even layer Press gently with a spoon so the sugar sticks to the butter Pour the cherry pie filling over this and use a spatula to spread it from edge to edge until the bottom of the pan is entirely covered You want a juicy layer with cherries distributed evenly so every bite gets some fruit

Make the Cake Batter:

In a large mixing bowl empty the chocolate cake mix Crack in the eggs add the oil water and vanilla extract Use a whisk or an electric mixer to beat everything together for about two minutes until the batter is thick silky and completely homogenous Careful scraping the sides of the bowl so no dry mix remains The batter should be smooth and glossy which means you have incorporated plenty of air for a tender cake

Assemble the Cake:

Pour the cake batter carefully over the cherry layer in the pan Start at one corner and slowly work your way across spreading gently with a spatula so you do not disturb the fruit underneath Cover all the cherries and smooth the surface of the cake

Bake:

Place the pan in the preheated oven on the middle rack Bake for thirty five to forty minutes Begin checking at thirty five minutes by inserting a toothpick in the center It should come out clean or with just a few crumbs not wet batter If not ready bake a few minutes longer

Cool and Invert:

Once the cake is baked set it on a cooling rack and let it rest in the pan for ten minutes Run a knife carefully around the edges to loosen any stuck bits Place a large serving platter upside down on top of the baking pan then quickly but carefully flip the pan and platter together Gently lift off the baking pan The cherry topping should be glistening on top of the cake If any cherries stick to the pan scoop them up and patch them back onto the cake Serve warm or at room temperature

Save

My favorite part of this cake is the molten cherry syrup that soaks into each piece it reminds me of the cherry pies my grandmother made but with the ease of a cake mix

Storage Tips

Store leftover cake wrapped tightly or in an airtight container at room temperature for up to three days If you prefer a firmer texture you can refrigerate it but let it come to room temperature before serving for the best moist crumb If you want to freeze the cake wrap cut pieces in two layers of plastic wrap and store in a freezer bag It keeps well for up to one month and can be thawed overnight in the refrigerator

Substitutions and Variations

If you do not have cherry pie filling you can substitute with homemade cherry topping or even another pie filling like blueberry or raspberry For a deeper chocolate flavor add a cup of chocolate chips to the batter If you want an extra grown up twist stir a splash of cherry liqueur into the cherry layer before baking

Serving Suggestions

Serve each slice with a big scoop of vanilla ice cream for the ultimate contrast of hot and cold A dollop of fresh whipped cream or a drizzle of chocolate sauce adds a touch of luxury I sometimes top with toasted sliced almonds or a sprinkle of flaky salt to amp up the flavors even more

Cultural and Historical Context

Upside down cakes have roots in American cooking traditions where fruit and sugar were layered under basic cake batters to create quick comforting desserts The combination of chocolate and cherries nods to European Black Forest cake but this recipe skips the fuss for a homier weeknight version Upside down cakes were especially popular in the mid twentieth century as canned fruit became widely available making them both nostalgic and practical

Recipe FAQs

→ Can I use fresh cherries instead of pie filling?

Yes, you can use pitted fresh cherries. Toss them with a bit of sugar and cornstarch before layering for best texture.

→ What pan size works best?

A 9×13-inch baking pan is ideal to ensure even layers and baking. Adjust baking time if using a different size.

→ Is it necessary to invert the cake while warm?

Yes, inverting while still warm helps release the cherry topping smoothly without sticking to the pan.

→ Can I make this dessert in advance?

Absolutely. Store at room temperature for up to three days, and briefly reheat if you prefer serving warm.

→ What goes well alongside this cake?

Pairing with vanilla ice cream or freshly whipped cream adds an extra treat to each serving.

→ Can I use homemade chocolate cake batter?

Yes, a homemade chocolate batter works well. Ensure it's moist and pourable for best results.