Chocolate-Chocolate-Chocolate-Chocolate-Chocolate Cupcakes (aka, Quintuple Chocolate Cupcakes)

Last week I had quite a few people ask me if Hubby or someone else was going to bake for my birthday. As someone who LOVES to bake, I really don’t mind baking my own cake (although the cake Hubby baked for me last year was amazing!). It’s an excuse to go all out and make a cake (or cupcakes) that’s totally over the top.

I had originally set out to make chocolate cupcakes filled with salted caramel and topped with ganache. But the first batch of chocolate cupcakes didn’t turn out and I was just too frustrated to continue with that idea. I needed to come up with something else for my birthday, but I’m sure I’ll go back to the salted caramel cupcake idea at some point.

I was perusing my Google reader’s cupcake tag and I saw these banana split cupcakes. Hello, beautiful! With those cupcakes as my inspiration, I came up with these quintuple chocolate cupcakes.

They start with an amazing chocolate cupcake. Next comes a swirl of chocolate cream cheese frosting. Then the cupcakes get dipped in a chocolate sauce and chocolate sprinkles. Last, another swirl of chocolate cream cheese frosting is added on top. These cupcakes were definitely over the top, super chocolatey, and the perfect cupcake to celebrate my birthday!

One Year Ago: Chocolate Mousse Cupcakes and Homemade Coleslaw
Two Years Ago: Goat Cheese and Roasted Red Pepper Toasts

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Quintuple Chocolate Cupcakes

Yield: 12 cupcakes


For the Quintuple Chocolate Cupcakes
12 chocolate cupcakes, recipe below
1 batch chocolate cream cheese frosting, recipe below
1 batch chocolate dipping sauce, recipe below
1 cup chocolate sprinkles (or jimmies, if that's what you call them)

For the Chocolate Cupcakes
2 oz unsweetened chocolate, chopped
1/4 cup Dutch-process cocoa powder
1 cup sugar
1/2 cup (1 stick) butter, cut up
1/3 cup water
1/2 cup milk
1 egg
1 egg yolk
1/2 tsp vanilla
1 cup flour
1 tsp baking powder
1/2 tsp baking soda
1/2 tsp salt

For the Chocolate Cream Cheese Frosting
8 oz cream cheese, at room temperature
1 stick unsalted butter, at room temperature
1/4 tsp salt
1 tsp vanilla
3 cups powdered sugar, sifted
3 ounces unsweetened chocolate, melted

For the Chocolate Dipping Sauce
4 oz dark chocolate, chopped
2 Tbsp heavy cream
4 Tbsp powdered sugar
5-8 Tbsp water, warm


For the Quintuple Chocolate Cupcakes
Bake the cupcakes and allow to cool completely in the pan. While the cupcakes are cooling, make the frosting.

Once completely cool, using a fat round tip, pipe a swirl on top of each cupcake. Place the entire tray of cupcakes in the freezer so the frosting will not melt while dipping it.

While the cupcakes are in the freezer, make the chocolate dipping sauce and allow it to come to room temperature.

Pour the chocolate dipping sauce into a small bowl (I used my 1-cup round tupperware bowls). You want it to be just larger in diameter than a cupcake, and fairly deep. Place the sprinkles in another similarly sized bowl.

Dip the cupcakes into the chocolate sauce until all the frosting is covered. Then add an edge of sprinkles by holding the cupcake sideways in the sprinkles and rotating until all sides are covered with sprinkles. Alternatively, you could just dip the whole thing in sprinkles if you want.

Place entire tray of cupcakes back in the freezer for the chocolate to set up.

Now using a fat star tip, pipe a smaller swirl on top of the cupcake. Store in the refrigerator.

For the Chocolate Cupcakes
Line a standard 12-cup muffin tin with paper liners.

In a heatproof bowl, combine chocolate and cocoa powder.

In a saucepan over medium heat, heat the granulated sugar, butter, and water, stirring occasionally, until the butter melts and the sugar dissolves. Pour the butter mixture over the chocolate and whisk until the chocolate melts and the mixture is smooth.

Whisk the milk, egg, extra yolk, and vanilla into the chocolate mixture until combined.

In a bowl, stir the flour, baking powder, baking soda, and salt until blended. Add the flour mixture to the chocolate mixture and whisk until smooth.

Let the batter sit at room temperature for 1 hour or cover and refrigerate for up to 3 days.

Set the oven at 350 degrees.

Divide the batter among the muffin cups. Bake for 30 minutes or until the tops spring back when pressed lightly with a fingertip. Set on a wire rack and leave to cool completely.

For the Chocolate Cream Cheese Frosting
Using a handheld electric beater, cream the cream cheese and butter together thoroughly.

Add the salt, vanilla, and powdered sugar.

Finally, mix in the melted chocolate and blend thoroughly until smooth.

For the Chocolate Dipping Sauce
Place chocolate and heavy cream in a bowl over simmering water. Let chocolate and cream sit for 2-3 minutes to melt without stirring. Slowly stir mixture to combine.

Add powdered sugar and mix to combine. Add water 1 tablespoon at a time, mixing after each addition until pouring consistency is reached. Set aside and let sauce cool to warm.

Chocolate Cupcakes Recipe from Joanne Chang, as seen in the Flour cookbook
Chocolate Cream Cheese Frosting Recipe from Food Network
Chocolate Dipping Sauce Recipe from Bakers Royale

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45 Responses to “Pumpkin Spice Cheesecake Brownies”

  1. #
    Becca — September 28, 2009 at 2:25 pm

    These look fantastic and are so festive!

  2. #
    The Woman — September 28, 2009 at 2:48 pm

    Oh my, these look divine! I recently made something similar, but with no chocolate – just a pumpkin batter with cream cheese topping. But I definitely think I must try these too.

  3. #
    ABowlOfMush — September 28, 2009 at 3:15 pm

    These are absolutely beautiful!

  4. #
    Carrie — September 28, 2009 at 3:41 pm

    Look wonderful!

  5. #
    oneordinaryday — September 28, 2009 at 4:54 pm

    These look awesome. I just wish it made a bigger pan!

  6. #
    Jen — September 28, 2009 at 4:56 pm

    They’re pretty rich, but I would imagine you could just double it and make it in a 9×13 pan if you wanted!

  7. #
    Ingrid — September 28, 2009 at 5:14 pm

    I made pumpkin spice brownies on Friday and they were delish so I bet these are EVEN BETTER! Thanks for sharing and I’ll be following your tweaks!

  8. #
    Justin — September 28, 2009 at 5:41 pm

    i always make a pumpkin cheesecake in the fall with a ginger cookie crumb crust, but i’m liking the chocolate component in your recipe even more.

  9. #
    Mia — September 28, 2009 at 5:49 pm

    oh yum – love pumpkin, and the chocolate/pumpkin combo looks wonderful!

  10. #
    Heather@BFM — September 28, 2009 at 6:03 pm

    These look great! Is there a way I can make them non-dairy? Something I can sub the cream cheese for? Thanks!

  11. #
    Jen — September 28, 2009 at 6:12 pm

    Heather – I’ve had great luck subbing Tofutti Better than Cream Cheese in cheesecake recipes in the past. I think that would definitely work and you could use Earth Balance in the brownie portion. Let me know how it turns out if you try it.

  12. #
    Jennifer — September 28, 2009 at 7:41 pm

    Hi Jenn! I just wanted to let you know that you won the giveaway on my blog last week. I emailed you, but never got a response. Could you email me your mailing address to I have to pass it along to myblogspark so they can send you your prize package!

  13. #
    Heather@BFM — September 28, 2009 at 8:11 pm

    Thanks, Jen…I’ll let you know how they come out!

  14. #
    nutmegnanny — September 28, 2009 at 9:01 pm

    OH wow these do look delicious! I love all that swirled pumpkin…yum!

  15. #
    Nina — September 29, 2009 at 4:29 am

    Those look amazing!

  16. #
    Irene — September 29, 2009 at 7:14 am

    Wow, I love these! My husband would die of happiness of I made these for him – pumpkin cheesecake is his favorite thing for fall.

  17. #
    thereddeer — September 29, 2009 at 12:25 pm

    They look like tiger fur – very cool! What an interesting flavour combination.

  18. #
    Colleen — September 29, 2009 at 6:26 pm

    We love these at my house! I like your idea of dark chocolate – I will have to try that next time.

  19. #
    stephchows — September 29, 2009 at 7:16 pm

    beautiful! And they look so delicious!! I agree I don’t normally think of pumpkin with chocolate… but you have me convinced!

  20. #
    Stephanie Wagner — September 29, 2009 at 11:55 pm

    The tops of these are a work of art! Love it!

  21. #
    Nancy @ Live love laugh — September 30, 2009 at 12:34 am

    Three of my favorite thi ngs in one dessert! Chocolate and pumpkin and cheesecake! How perfect…

  22. #
    Nancy @ Live love laugh — September 30, 2009 at 12:34 am

    Three of my favorite thi ngs in one dessert! Chocolate and pumpkin and cheesecake! How perfect…

  23. #
    tagskie — October 1, 2009 at 8:00 am

    hi.. just dropping by here… have a nice day!

  24. #
    Pantry Raid Blog — October 6, 2009 at 2:58 am

    The side-view shot totally won me over. These look delicious!

  25. #
    bakingsimplicity — October 6, 2009 at 2:21 pm

    This looks so yummy.
    I now know what to make for the office potluck!

  26. #
    Skylar Wolfe — October 12, 2009 at 7:39 pm

    Those look amazing. I love pumpkin with chocolate, I plan on making these soon.

  27. #
    fawkes — October 14, 2009 at 5:14 am

    Your brownies look delicious! I am curious since I would like mine to taste more like pumpkin pie than plain pumpkin should i add pumpkin pie spices or follow your recipe for the spices?

  28. #
    Jen — October 14, 2009 at 12:03 pm

    fawkes – There are a decent amount of spices in the pumpkin portion of the batter. I would recommend making is as the recipe states, then taste it before you pour it into the pan. Maybe then add some pumpkin pie spice if you’d like.

  29. #
    lifeoftheparty — October 20, 2009 at 1:42 pm

    I made these over the weekend and they were scrumptious!! I’m not a huge fan of pumpkin but this recipe is now a fall staple. I plan on making them for the family on Thanksgiving…thanks for sharing this!

  30. #
    strmywthr3 — October 21, 2009 at 1:06 pm

    I made these the other day and they were great! a hit at work! yum! thanks!

  31. #
    malelanie — October 29, 2009 at 2:21 pm

    I stumbled across your blog from a Facebook friend and made these brownies last night. DELICIOUS!! I doubled the recipe and it does just fit in a 9×13 pan and took about 60 mins to bake. It’s worth the wait for them to be chilled in the fridge. The flavors are even more delicious that way.

  32. #
    Dorothy — October 29, 2009 at 8:00 pm

    Oh YUM! And gorgeous, to boot. I never thought pumpkin and chocolate go together either, until I tried it! 🙂 Now I’m hooked. Good idea to double up on the cheesecake layer…you can never have enough pumpkin cheesecake after all!

  33. #
    nutmegnanny — October 30, 2009 at 3:10 pm

    Thank you so much for participating in our event! These brownies look amazing. They say Halloween to me for sure!

  34. #
    Shortcake — November 2, 2009 at 4:52 pm

    I made these– now I love them! Will be repeated each fall 🙂

  35. #
    Lexi — January 4, 2010 at 3:54 pm

    Amazing! I loved these so much I played with them a bit and made cranberry cheesecake brownies for my christmas baking.(I didn’t stumble on to these till christmas.) I’ll let you know when I put those up on my blog! With credit to you of course!

  36. #
    Jen — January 4, 2010 at 3:59 pm

    Lexi – cranberry cheesecake brownies sound very intriguing. Can’t wait to see them.

  37. #
    Kasey — March 3, 2010 at 1:37 am

    Hi Jen! I made these for Heather@BFM’s (comment listed above) birthday and she loved them! Unfortunately I could not find the Hershey’s Special Dark cocoa powder (I tried 3 stores) so I had to make them with the regular cocoa powder. Can you tell me where you found the Hershey’s Special Dark??

  38. #
    Jen — March 3, 2010 at 1:57 am

    Kasey – I have actually had a hard time finding it as well. I had actually all but given up on it until one day it caught my eye at the grocery store. I proceeded to buy all three containers. I would say just keep an eye out for it and good luck!

  39. #
    Pup Wanna Be — September 28, 2010 at 12:35 am

    1/2 cup of flour seems like very little. Is that correct?

  40. #
    Jen — September 28, 2010 at 12:50 am

    Pup – Yes, that is the correct amount of flour. Most brownie batters have very little flour in them.

  41. #
    rachellehcar — September 29, 2010 at 1:39 am

    Just made these- delicious! I only had the milk chocolate powder, so I’m excited to try it again with the special dark powder.

  42. #
    Courtney — September 13, 2012 at 6:35 am

    I doubled the recipe and it perfectly filled a 13×9 pan so you might try it. 🙂 And they are amazing. Also I used margerine not butter and found they were more moist. Happy Baking!

  43. #
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  45. #
    alyssajade23 — October 12, 2014 at 4:15 pm

    I made these with my nieces and over all they were pretty good, but something about the pumpkin part tasted off. Still, fun and festive to make!

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