Quintuple Chocolate Fudgy Brownie Cookies

These cookies are for the serious chocaholic. Five different types of chocolate is used.

Yes, five: cocoa powder, bittersweet baking chocolate, semi-sweet chocolate chips, chocolate truffles, and chopped chocolate-filled Oreo cookies.

A couple weeks ago I received some chocolate truffle cookies and I wasn’t able to get them out of my mind. Rather than buying them for two dollars each because I’d go broke in a day, I attempted to loosely recreate them.

I cross-referenced, halved, and adapted the recipe for Thick and Chewy Brownie Cookies from one of my favorite cookbooks, The New Best Recipe from Cooks Illustrated. I am a huge fan of Cooks Illustrated and America’s Test Kitchen because they test and trial every possible combination of ingredients and methods in a recipe, including whether to melt or cream the butter and how much to use, whether to use granulated or brown sugar and in what ratio, whether eggs should first be whisked before being added to the batter, how many including whole eggs plus yolk combinations, and on and on. They take the guesswork out of recipes for almost-guaranteed success.

II was going to put this much chocolate into a recipe, I wanted to know that not only would it work, but that they would be the best chocolate cookies I had ever tasted. I got my wish.

This recipe dirties plenty of little bowls, but the payoff is worth it. First sift together the flours, cocoa powder, baking soda and optional salt. Although the Cooks Illustrated recipe exclusively uses all-purpose flour, I used both bread and all-purpose flour because bread flour creates extra chewiness and I love brownies and cookies with chewy edges. Using exclusively all-purpose will be fine, but the cookies may not have as much structure, may not hold their shape quite as well and may flatten a bit while baking, and will be a bit less chewy overall.

The Cooks Illustrated recipe also calls for Dutch-process unsweetened cocoa powder, which tends to be more expensive than natural unsweetened cocoa powder. Dutch-processed cocoa has been treated with an acid to neutralize it’s acidity and will not react with baking soda and baking powder must be used. Brands like Droste, Vahlrohna, and Ghirardelli are Dutch-processed; Hershey’s and Trader Joe’s are not. I successfully relied on the trusty Trader for my cocoa powder. Chocolate use number one.

Next, melt eight ounces of  bittersweet or semi-sweet or baking chocolate or a favorite dark chocolate bar. Because the richness and intensity of these cookies comes in large part from this choice of chocolate, use a chocolate bold and intense enough to pack a punch. I used a 72% Pound Plus bar and would caution against using melted chocolate chips based on both their structural properties and taste. Chocolate use number two.

In another bowl, combine the eggs, vanilla, and lightly beat them. I did as the recipe instructed and beat the eggs, but did not follow directions when it came to adding the vanilla and added a little more. I love vanilla.

With a mixer, beat five tablespoons of butter, which is just over half of a stick for the whole recipe, which I find impressive. Cream the butter with mostly brown sugar and just a bit of granulated. The much higher brown-to-white sugar ratio boosts flavor, and encourages the cookies to stay soft and moist for days because brown sugar absorbs moisture in the air, rather than drying out.

After creaming together the butter and sugar, then adding the egg-vanilla mixture, and then the sifted dry ingredients, the fun part begins by adding one cup of semi-sweet chocolate chips. Chocolate use number three.

I departed here from the Cooks Illsutrated recipe and wanted to channel the Cravory Cookies I had tried and added one-half cup diced chocolate truffles, about three average-sized truffles chopped into pieces about the size of a chocolate chip. Some of truffles I used had a caramel filling. Chopped candy bars such as Snickers, Twix, Reese’s Peanut Butter Cups, Rolos, or similar candy bars may be substituted, and a couple fun-sized bars or half of a full-size bar should do the trick. Chocolate use number four.

The fifth and final chocolate use comes from adding six chopped Oreos cookies, about one-half cup, to the batter. I used chocolate-filled Oreos because I had them on hand, but if you have white-filled Oreos, those will be just fine. All the crumbs that inevitably make a mess on the counter when chopping the Oreos do wonders for absorbing dough moisture. The Oreos do for the cookies what Rice Krispies did for Peanut Butter Chocolate Chip Granola Bars, providing a remarkable pop of texture for something so small.

The dough is fairly thick but also soft, and needs to be refrigerated for at least thirty minutes before baking, which is what the Cooks Illustrated recipe recommends. I recommend at least two hours, up to five days. I didn’t bake the cookies until three days after I made the dough and it was rock hard due to melted chocolate re-solidifying, but came up to room temperature in twenty minutes and I formed it into mounds.

I wanted these cookies to be large, but not huge, and used 2.25-ounce mounds of dough for each cookie, weighed on a digital scale. If you don’t have a scale, using a heaping dollop of dough from a two-tablespoon cookie scoop is a good approximation. The mounds of dough will look quite large, but remember that the Oreos and truffle pieces don’t weigh much but they bulk up the dough, adding visual heft without actual mass.

Bake the cookies until the tops are just set, about ten minutes, and do not overbake them. Lke all cookies, they will set up quite dramatically as they cool. If the cookies stayed domed and mounded while baking like mine did, tap the top of each mound lightly yet firmly with the back of a spoon or push down very gently with the bottom of a drinking glass or measuring cup to flatten them. If after flattening the cookies are very soft, return them to the oven for one or two more minutes. Mine were soft to the point of raw after flattening so I returned to the oven for ninety seconds, for a total baking time of 11 minutes. Allow the dark beauties to set up on the baking trays for five minutes before moving them to a rack. Or moving them into your mouth.

Each layer of chocolate is notable and has a purpose. The cocoa powder and melted bittersweet baking chocolate both impart chocolate intensity into the dough. The former dries the dough and acts more as flour and the later moistens it. Both have a role in creating a cookie dough base that’s deeply chocolate-flavored.

The chocolate chips and chopped truffles add texture, richness, and luxuriousness. Biting down into a melted and oozing chocolate truffle that’s surrounded by firm yet moist cookie dough is magical. Finally, the chopped Oreos add bits of sandiness and crunch.

With their chewy edges and soft centers, accentuated by the rivers of melted chocolate chips melted truffles running through them, the cookies are reminiscent of a decadent fudgy brownie. They’re rich and bold, and not overly sweet. They’re dense, decadent, and soul-satisfying.

They are the cookie you want when you’ve had a horrible day, are PMSing, your rent is due and you don’t know how you’re going to pay it, or when you need a hug. They’re also the kind of cookie that would be elegant enough to serve after a fancy dinner party or to put out on a holiday party platter. They would make fabulous and memorable gifts that the recipient won’t soon forget.

One is all you need. Unless you’re like me and could live on cookies, especially ones with five types of chocolate in them.

Quintuple Chocolate Fudgy Brownie Cookies

Prep Time: 20 minutes

Cook Time: 10 minutes

Total Time: 30 minutes

Yield: About 18 cookies

These cookies are for the ultimate chocolate lover. Chocolate is used five times: Cocoa powder, melted bittersweet baking chocolate, semi-sweet chocolate chips, diced chocolate and caramel-filled truffles (or use your fave diced candy bar) and chocolate-filled Oreo cookies.

The cookies are a play on cookies I sampled from a popular online site, The Cravory. I succeeded in packing even more dense, fudgy, rich, soul-satisfying chocolate in these cookies than in their cookies or in any cookie I've ever made previously. Soft, chewy, and they're not overly sweet; they're a mature chocolate lover's cookie, bold and full of diverse textures and unadulterated chocolate intensity and they just melt-in-your mouth.


1/2 cup all-purpose flour

1/2 cup bread flour (using 1 cup total of all-purpose may be substituted, see note below)

1/4 cup unsweetened natural cocoa powder

1 teaspoon baking powder

1/4 teaspoon salt, optional and to taste

8 ounces bittersweet or semi-sweet baking chocolate or dark chocolate bar (I used Trader Joe's 72% Pound Plus Bar)

2 large eggs, lightly beaten

1 1/2 teaspoons vanilla extract

5 tablespoons unsalted butter, softened

3/4 cup light brown sugar, packed

1/4 cup granulated sugar

1 cup semi-sweet chocolate chips

about 1/2 cup chocolate truffles, chopped (2 or 3 average-sized truffles, mine were caramel-filled; truffles may be substituted with 2 or 3 chopped mini-candy bars or half of a full-size candy bar such as Twix, Snickers, Reese's Peanut Butter Cups, Rolos)

about 1/2 cup chocolate-filled Oreo cookies, chopped (6 or 7 Oreos) - optional but recommended, see note below


In a medium-sized bowl, sift together the flours (the Cooks Illustrated recipe exclusively calls for all-purpose but I prefer a blend of all-purpose and bread flour for chewier cookies; if you don't have bread flour, exclusively using all-purpose is okay but cookies won't have quite as much structure or be as quite as chewy) cocoa powder, baking powder, and optional salt; set aside.

In a medium microwave-safe bowl, melt the baking chocolate on high power for about 1 minute, stir, and continue to melt in 30 second increments until fully melted and can be stirred smooth; set aside.

In a small bowl, whisk the eggs and vanilla; set aside.

To the bowl of a stand mixer fitted with paddle attachment, beat the butter until smooth and creamy, about 1 minute. Add the sugars and beat to incorporate and mixture is unform, 1 to 2 minutes, noting the mixture will be granular. Add the egg-vanilla mixture and beat until incorporated, about 1 minute. Add the melted baking chocolate and beat until combined, about 1 minute. Add the sifted dry ingredients and beat to just incorporate them, about 1 minute. Do not overmix batter at any point in the process.

Add the semi-sweet chocolate chips, chopped truffles (or chopped candy bar pieces; chopped to the size of a chocolate chip or just slightly larger) and the chopped Oreo cookies and beat for 10 seconds to just incorporate or fold in by hand (I used chocolate-filled Oreos because I wanted all-chocolate, no white in the dough, but traditional white-filled Oreos may be used; chocolate graham crackers may also be substituted. The Oreos and their resulting crumbs help soak up some of the moisture from the batter and if not using them you may consider increasing the flour by 1 to 2 tablespoons as well as adding slightly more semi-sweet chocolate chips or truffles/candy based on how your batter looks). Chill dough for at least 30 minutes and up to 5 days before baking. Note that unbaked cookie dough can be formed into balls and stored in an airtight container or ziplock in the freezer for up to 3 months and baked straight from freezer to oven, extending baking time by a minute or two if necessary; this is nice so you don't have to bake all of them at once as they are rich.

Preheat oven to 350 F and line two baking trays with Silpat Non-Stick Baking Mats or spray with cooking spray, set aside. If necessary, allow dough to come to room temperature for 5 to 10 minutes and scoop out 2.25 ounces of dough, weighed on a scale (approximately a scant 1/4-cup measure or a heaping 2-inch cookie scoop) and place mounds on a baking tray, spaced about 2 inches apart. I bake 8 to a tray, maximum.

Bake for about 10 minutes, or until the tops have just set, even though the centers will seem soft or slightly underbaked, as the cookies will set up quite dramatically as they cool. If the cookies stayed domed and mounded while baking (mine did), tap the top of each mound lightly yet firmly with the back of a spoon or push down very gently with the bottom of a glass to flatten them. If after flattening they seem very soft, return to the oven for 1 to 2 more minutes (mine were soft to the point of raw after flattening so I returned to the oven for 90 seconds; total baking time was 11 minutes). Allow cookies to cool on baking sheets for at least 5 minutes before transferring to a wire rack to cool completely. Cookies will keep in an airtight container for up to 5 days or in the freezer for up to 3 months.

Adapted from the The New Best Recipe cookbook


Related Recipes:

Dark Chocolate Chocolate-Chip Cookies Stuffed with Chocolate Covered Strawberries – Any dried fruit may be used but there’s something about the combination of chocolate and chocolate-covered strawberries that is especially good. Strawberries and chocolate shouldn’t only be for Valentine’s Day

Molasses Triple Chocolate Cookies – Chocolate is used three ways for maximum gooeyness in these new seasonal favorite cookies. Soft, moist, tender, no mixer is required, and if you’ve never paired chocolate together with molasses, it’s a great combo

Chocolate Chip and Chunk Cookies – My new favorite chocolate chip cookie recipe for soft, chewy, fabulous cookies that are easy and straightforward to make, and yield my definition of perfect-cookie results, with two types of chocolate used

Mounds Bar Chocolate Coconut Cake Mix Cookies – Chocolate and coconut is a winning combination and I baked both chocolate chips and Mounds Bar candy bars into these easy, goofproof chocolate cake mix cookies that turn out soft and moist every time

Flourless Chocolate Peanut Butter Chocolate Chip Cookies (gluten free) – Chocolate and peanut butter is perhaps the best chocolate pairing of all time and these cookies use chocolate two ways, cocoa powder and chocolate chips, along with a hefty does of peanut butter

Chocolate Cake with Chocolate Ganache –  This is my go-to chocolate cake recipe because the cake turns out moist, rich, and has great depth of flavor. The batter comes together in just minutes with a whisk and is just as fast as using a boxed cake mix, with much more scrumptious results along with the smooth, silky and creamy chocolate ganache

Frozen Chocolate Pudding and Wafer Cake (No-Bake, 3 ingredients) – Chocolate pudding and chocolate wafers are layered for a frozen and no-bake fun icebox cake, with wafers that stay crisp. Many ice box cakes made from graham crackers have a tendency to turn mushy and disintegrate but not this one

Fudgy Nutella Brownies with Cream Cheese Frosting – Nothing cakey at all about these fudgy, dense, rich brownies. The recipe is as easy as using a boxed mix with far superior taste and the batter comes together in less than five minutes with a whisk. Nutella swirls and cream cheese frosting optional, but recommended

Chocolate Molasses Chocolate Chip Cake with Baileys Irish Cream Glaze – Both cocoa powder and chocolate chips give this easy cake a rich depth of flavor, complemented by the molasses. The glaze is good enough to want to drink

Do you have a favorite chocolate recipe for cookies, cake, brownies, or bars? Are you a chocolate lover?

Feel free to link up your favorite and intensely chocolate recipes.

There are certain times where I can go for a week, or longer, without having any chocolate. And then, when the craving hits me, I have to have it and nothing else will do. And that’s when I make things like this. I figure as long as there’s health benefits in chocolate, I may as well capitalize on all of those benefits.

Thanks for the Nielsen-Massey Vanilla Sampler Giveaway entries


  1. Pingback: Chocolate Recipes

  2. Oh sweet chocolate, it is the best. Possibly better than vanilla. Or not! I linked this yesterday because you asked for vanilla recipes, but the first chocolate-y thing I thought of as an answer to your question was this cake: http://scrumptiousgruel.wordpress.com/2012/08/29/chocolate-and-vanilla-its-not-so-black-and-white/
    Second thing I thought of was this Chocolate Black Russian:
    Your recipe looks divine-I need to try the chocolate Oreos!

  3. Oh my gosh Averie are you kidding? They look INSANE! I want one, right now. Wish I could reach right into the screen. And 5 types of chocolate?! You’re amazing :-)

  4. Holy chocolate! I love chocolate–the darker the better. The 72%bar from TJ’s is delicious, no? This looks amazing!

    • That bar is my #1 go-to for all my melted chocolate needs. Every once in awhile it’s better to use chocolate chips and I will (and I love the TJ’s choc chips) but that 72% bar can do no wrong!

  5. Nothing worse than finding a food that would make you go broke in a day. No better way than to recreate it, save a bunch of money AND put it on the blog! Win, win, win all around :D

  6. Am i dreaming??? this is the best cookie’s recipe i’ve ever seen!

  7. Get in my mouth you delicious looking chocolate cookie! Averie, these just blow my mind…5 chocolates? Heavenly!

  8. SO much chocolate! I mean, worst case scenario, if they didn’t work out, you would just have to eat the dough… : )

  9. If these cookies are for a serious chocoholic then these are for ME!!

  10. those look insanely good! Hope you had a great weekend!

  11. Rivers of melted chocolate? Holy cow Averie I am wishing I had a plateful of those for breakfast instead of the eggs I just ate. Love love love all the different chocolate textures you packed into these awesome cookies!!!

  12. I am always impressed by you! Not only do you post every.single.day, but each recipe is just as good as or better than the last! I adore dark chocolate and this cookie would meet my chocolate needs any day of the week.

  13. So much amazing chocolate in the post Averie!

  14. I’m LOVING the chocolate overload. Sometimes you just need a chocolate fix, and why not go all out. These look so rich and scrumptious. Need to keep this recipe in mind for when I’m having serious chocolate cravings!

  15. Why oh why do you post these delicious recipes so early. I have no sweet tooth this early (shocking, I know.) Actually….it’s probably best that way. :D

  16. These look very good and just evil seeing them before breakfast! :-) Awesome job and great pics as usual!

  17. Wow. Serious wow.

    I have that cookbook and am obviously not using it to it’s full potential!

    • I wasn’t using it to it’s fullest potential either until I saw a friend make this recipe and was like wait, how did I miss those?! The only drawback to that cookbook is that there are no photos and there’s line-sketched drawings, circa 1968. It would be so awesome if they had photos for at least some of the recipes!

  18. Girl, another amazing cookie recipe. You are rocking them lately. I’m so envious of you being in Aruba right now. We just a series of storms up there that dumped roughly a foot of rain and the winds were crazy. I am so not a rainy day girl. Give me my sunshine! I may pick up that book, but I belong to their website and pay annually for that, so I may check it out from the library first to see if there is anything unique in the book!

    I hope you’re getting a nice run along the ocean today!

  19. I have a t-shirt that says “I’ll be nicer if you give me chocolate”. I think these cookies would make me downright angelic!! They look absolutely DIVINE! My inexpensive Procter Silex toaster oven is at least 18 yrs old and it has been up in the attic for the last 15 yrs. I was a little shocked that it still worked because our attic is over the garage so it has gone through some pretty extreme temperatures. I think I’d definitely want it in a warm climate–it wouldn’t heat the kitchen up nearly as much as a larger oven.

    • Thanks for the info on the P-S 15 year old toaster oven and that it has hung on like a champ all these years – wow! I think I need to investigate them more for my next trip here.

      And yes, the cookies are downright angelic. They are so deep and fudgy and rich and just…amazing. I wish I had one right now!

  20. Holy macaroni. This is a chocoholic’s dream right here! Look how dark and fudgy these bad boys are. How glorious!

  21. Since the holidays put me in the mood for chocolate-mint everything, here’s my favorite chocolate recipe of the moment: DOUBLE DARK CHOCOLATE MINT CHIP COOKIES. Yay for chocolate in multiple ways!

  22. These cookies are amazing. Another great recipe from Averie!

  23. 5 types of chocolate? yes, yes, yes. i’m totally on board with that! YUM!

  24. Wow, these definitely take chocolate cookies to a whole new level! Plus 5 Tbsp of butter…that is impressive.

  25. serious chocolate cookies!
    for those times when you are craving chocolate like mad!
    these could be labeled as medicine cookies, for us women. lol

  26. Um… yes, please! My name is Becky and I’m a choco-holic. I am going to have to save this recipe for a cookie exchange or party – I’ll eat the entire batch if I make them for home! :)

  27. 5 types of chocolate in 1 cookie?! My mind is blown!

  28. I think I just died of a chocolate overload. I’m not complaining, though.

  29. Seriously these look amazing!!I love all the chocolate. And I totally agree Cooks Illustrated and Americas Test Kitchen are the best!

  30. That is some -serious- chocolate. Wow!

  31. Those look amazing! And I completely love Cooks Illustrated as well, they have taught me so much.

  32. I like your approach to chocolate treats. Amp the chocolate to the max! There is no way I am sharing these cookies with anyone! All for me :)

  33. So, I am definitely not the most serious chocoholic that ever lived but I love that you used so many different kinds in these. Chocolate perfection, for sure!

  34. Averie – you know I’m a major chocoholic! These cookies were made for me… right??! Definitely going on the “make” list! Maybe they’ll even be santa’s cookies for christmas eve ;)

  35. woah. Woah. WOAH. These cookies truly are a chocoholic’s dream come TRUE! I love the ways that you incorporated chocolate into this recipe, Averie, and I also LOVE that you used bread flour. What a wonderful treat these cookies are, especially at this chocolate-loving time of year!! :)

  36. Ha, my boyfriend just saw these cookies (he’s even bigger on chocolate than me) and gave me the “please make those” look. A winner!

  37. I am in total LOVE with these! They sound so fabulous!

  38. Anyone who knows me knows how obsessed I am with chocolate. I even did research papers and gave presentations on chocolate in elementary and high school because I love it so much. I bow down to you for creating the world’s most chocolatey cookie – I would push aside and step over my own grandmother for one of these babies!

  39. Avery, I love your opening statement: “These cookies are for the serious chocaholic”. I can’t stop giggling… sorry… :) Although I am not team chocolate, I do make some steps in that direction: last week we had a lunch with girls, and I ate a whole chocolate medallion (about the size of the quarter)! See, told you I am making progress! I do love the idea of those cookies, they look very chocolaty, great for the holidays with a glass (or cup) of mulled wine… next to a fireplace somewhere in mountain lodge… :)

  40. Wow, I don’t think it would be physically possible to squeeze any more chocolate into these little cocoa bombs- And that’s really saying something!

  41. If these are anything like your fudgey nutella brownies, I need to make these asap. Also, I love your explanations about why you select whatever ingredients so select. Food science is the best kind!

    • They actually are better. The brownies are really, really good. But these cookies are just…insanely good. Diced truffles and five forms of chocolate will do that for a recipe :) And glad you like the food science – too often I read recipes and am bewildered from how the person got from point A to B and I try to explain things!

  42. Well you already know I’m not a chocolate fan, however, these would be that ideal treat to take to a party. Talk about everyone loving me! ;-)

  43. I die. These are lovely!

  44. They all look so delicious!

  45. Are you kidding me? I am DROOLING right now. Wow! So many great chocoholic recipes here. The chocolate molasses Bailey’s cake sounds FAB-U-LOUS! I am SO making it this week.

    Thank you for sharing!

  46. You had me with the pictures. I think you could have put chopped up doggie biscuits in those cookies and I would have eaten them because the pictures make them look so ooey gooey good. But I am happy that they are indeed chocolate. Now the quintuple part made me pin this on my Recipes To Try board. I don’t think I have seen so much chocolate in a cookie before and I am a sucker for chocolate. You out did yourself with this one. And I enjoy reading all your knowledge on the science of baking.

  47. i swear by the cooks illustrated choc cookie recipe and i’m so glad you tried it Averie – with some variation! It does require a ton of different bowls, which annoys me, but the end result is SO worth every little dish am I right? The addition of Oreos? Ok I love you. The addition of truffles? HOLY COW are you serious? These cookies are crazy. full of anything and everything chocolate and I don’t think you could squeeze it in in any other way! These truly look like the perfect chocolate cookie recipe – one for a true chocoholic. my sister is the QUEEN of chocolate… (she hates fruity dessert.s.. how are we related?!) and she would go mad if I showed her this. Which, I’m going to. Obviously. :)

    • I know you love this cookie dough base and I have to say, it’s awesome! The truffles and Oreos just took it to new levels…and if your sis is a chocaholic, this is SO her cookie! And yes, I had half my kitchen dirty with little bowls but it was worth it :)

  48. Holy moly – so. much. chocolate. Incredible! I’m the same way – when a chocolate craving strikes I need the real deal. Have you ever tried those chocolate truffles they sell at Trader Joe’s, Averie? They are divine, and I’m thinking they could probably be chopped up and added to these super chocolate cookies.

    • No I havent had those – I have had soooo many TJs things and candies and baking items and just basically I am a a TJs fiend and have to put limits! on myself or I want to buy out the store. I will look for them next time I’m back in the States and at TJs! :)

  49. Oh my gosh, I can’t believe these! You went big, to say the least… I love the idea of changing up the mix ins (the peanut butter cups suggestion caught my eye!).

  50. ok i need to start reading your blog in the morning because i usually read at like 10 pm and it makes me starving!

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