Chocolate Bourbon Pudding Squares

I am impatiently awaiting spring to spring. We've gone from 50 to 90 to 30 degrees and back, but there is nary a rhubarb stalk—the baker’s flag for spring—at my farmers market stalls. With recipes like this jam, this drink, this cookie, and this pie or this tart calling to be made, it felt unnatural to venture back into my winter fruit reserves and preserves, hence: chocolate. These pudding squares aren't a thumb-twiddling option or runner-up to rhubarb, even in spite of my using them as a seasonal in-betweener. This is a bona fide delicious dessert that has been calling ever since I hoarded Alice Medrich’s cookie book from the library and wondered just how in gravity’s name the pudding sides stay up like that. They are so good—like a more boss brownie. 

I made these late last week for a special occasion that has become all-too infrequent over the past few months, namely a visit from my beautiful musical friends in Richmond who came up to DC to play a show in our newly refurbished basement space. We stayed up until the wee hours drinking a leftover bottle of New Year’s (maybe?) champagne and shooting the shit with the yarn-spinner of all time before waking up early to scarf bagels and visit RVA for the day. From whence, we decided it would be a pro decision to make and consume 18 deviled eggs (albeit delicious ones!) in less than two hours, which has led to my forever swearing off my latest favorite food; I still feel a little green. The visit revolved around food and talks and was way too short, all as always, and it made me even more antsy for spring and summer, which are both best spent lazing on rocks and flailing in the James. Or, as it were, eating chocolate-bourbon pudding bars and waiting for the rhubarb to show up. Hope you like these!


Chocolate Bourbon Pudding Squares
Adapted from Alice Medrich's Chewy, Gooey, Crispy, Crunchy


For the crust
7 tablespoons unsalted butter, melted and still warm
¼ cup light brown sugar, packed
½ teaspoon pure vanilla extract
½ teaspoon fine-grain sea salt
1 cup unbleached all-purpose flour
2 ounces semisweet or bittersweet chocolate, chips or chopped bar

For the filling
¼ cup granulated sugar
⅓ cup unsweetened cocoa powder
2 tablespoons cornstarch
⅛ teaspoon fine-grain sea salt
1 ½ cups whole milk
½ cup heavy cream
5 ounces semisweet or bittersweet chocolate with up to 62% cacao, finely chopped
1 teaspoon pure vanilla extract
1 tablespoon bourbon (Medrich uses rum)

1.  Line an 8-inch square metal baking pan on the bottom and all four sides with foil. Preheat the oven to 350 degrees F. Position a rack in the lower third of the oven.

2.  In a medium bowl, combine the melted butter with the brown sugar, vanilla, and salt. Add the flour and mix just until blended. The dough will be soft and oily; that’s fine! Press the dough evenly over the bottom of the lined pan. Bake for 15 to 20 minutes, until the crust is deep golden brown at the edges. Remove the pan from the oven and immediately sprinkle the chopped chocolate over the hot crust. Let stand for about five minutes to melt the chocolate. Use a rubber or offset spatula to spread the chocolate over the surface of the crust in a thin but thorough layer. Let the crust cool and then refrigerate while you make filling, until chocolate is set.

3.  In a heavy, medium saucepan, whisk the sugar, cocoa, cornstarch, and salt to blend. Add about three to four tablespoons of the milk and whisk to form a smooth paste. Whisk in the remaining milk and the cream. Heat the mixture over medium heat, stirring constantly with a flat-ended heatproof spatula or wooden spoon and scraping the bottom, sides, and corners of the pan to prevent scalding until the pudding thickens and begins to bubble at the edges, five or six minutes (mine actually went for eight). Add the chocolate, vanilla, and rum and stir a bit faster to smooth out the pudding for about 1 ½ minutes. Scrape the hot pudding onto the crust and level it with one or two strokes of the spatula.

4.  Let the pudding cool, undisturbed (without mixing, jiggling, or spooning out a taste), at room temperature for one hour. Refrigerate the pan, uncovered, until the pudding is completely cool. Cover it and chill for at least several hours or overnight.

5.  Use the edges of the foil to lift the bars from the pan and transfer to a cutting board. Cut into 16 squares. Medrich also suggests cutting round “bars” with a biscuit cutter, but I couldn’t bear to leave the scraps! Dust with cocoa powder and/or powdered sugar to serve. Squares will keep covered in the fridge for about three days.

Bittersweet Chocolate Pudding

Last Saturday morning, I woke up with a head cold and a pudding hankering and decided that answering my craving would remedy my illness. Well it did, but not until I had navigated through a minefield of pudding recipes that called for everything from water baths and oven time to egg yolks and butter.  My favorite butterscotch pudding recipe takes 15 minutes to make and 30 to cool, yet I found one chocolate pudding recipe (highly rated at least) that called for seven hours of total preparation time and another that required two pots, a blender, and some baking—egads that's unreasonable. Thankfully, Smitten Kitchen had the answer, and this intense, chocolatey pudding emerged after 24 minutes of practically unattended cooking and one nap's worth of chill time in the fridge—a delicious, three-step cure to any cold.

Bittersweet Chocolate Pudding
Adapted from Smitten Kitchen

1/4 cup cornstarch
1/2 cup sugar
1/8 teaspoon salt
3 cups whole milk
6 ounces bittersweet chocolate, chopped (I used 60%, you could also do high-quality semi-sweet for more classic flavor)
1 teaspoon pure vanilla extract

1.  Combine cornstarch, sugar, and salt in the top of a double boiler.  Slowly add the milk, whisking to make sure all of the dry ingredients are incorporated.  Place over gently simmering water, and stir occasionally, making sure to scrape the bottom and sides with a heat-proof spatula.  Use a whisk as necessary to prevent lumps.  After 15 to 20 minutes, mixture should be thick enough to coat the back of a spoon.  Add chocolate, and continue stirring for about four minutes until pudding is smooth and thickened.  Remove from heat and add vanilla.

2.  Strain pudding through a fine mesh sieve into a large bowl or measuring cup with a pour spout.  Discard lumps from strainer, and divide pudding between six bowls.

3.  Place plastic wrap directly atop pudding if you don't like pudding skins, or just over the bowl if you do.  Chill in the refrigerator for 30 minutes to an hour (mine was at a good, cool pudding temperature after an hour).  Pudding will keep, covered and refrigerated, for up to three days.

Vanilla Bean and Whiskey Pudding Tartlets

My sister’s apartment is sort of an apocalyptic mess. She has three rolling pins I can never find, always appears to have some sort of meat carcass in her fridge waiting to be cooked into stock, and on my most recent trip to Pittsburgh, also had an ice formation in her freezer that I think she left there because it looks like, well, a certain male bathing-suit part. Her apartment is scattered with clothes, children’s books, crafting things, leftover art, and library DVDs, and also, she keeps ceramic figurines of ambiguously rendered farm animals in her plants (the donkey-cow-pig, for instance). There are wool sweaters in the freezer too, and the contents of a jumbo box of Nerds spilled across her coffee table.

Oh hai! I'm just a stack of pans, chillin' in the freezer with an icy phallus.

My cataloguing of her domestic detritus might not show it, but my sister is flat out my hero. The Atlantic published an article in May noting that 93% of the happy and healthy adults Dr. George Valliant measured in his lifelong psychological study on happiness had had good relationships with a sibling when younger. Well, from partnering to steal all the neighbors’ sample boxes of cereal, to getting the pride kicked out of me in every single board and card game ever, to catching tadpoles and crawdads in New Hampshire and jumping into slimy lakes and an eel-filled quarry in Maine, we have the kind of relationship reinforced by frozen wool sweaters, moldy dishes, and other things that take the sort of roundabout way to get where they're going. And when not preserving phallic ice sculptures or eating Vietnamese soups full of MSG, sometimes we make things in the kitchen. This time, it was failed butterscotch tartlets that turned into a serendipitous, vanilla-whiskey mistake, which I think sounds just about right, all things considered.

To keep the inside of the freezer warm.

Sometimes Whole Foods just, aherm, gives vanilla beans away.

Vanilla Bean and Whiskey Pudding Tartlets (with Chocolate Espresso Beans)
Adapted clumsily from Baked! New Frontiers in Baking

This recipe was supposed to make butterscotch tartlets, but they came out vanilla-y. I might not have cooked the caramel long enough and that's what did it, but I was using raw sugar, so it looked a little "amber-colored" from the get-go. Whatever I did wrong, these still tasted really excellent, and the whiskey adds a great punch to the vanilla. If you want to limit the butterscotch taste, simply do not caramelize the sugar. You might wonder what the point of going to the hassle of crusts is. I still wonder. In the end, they add some buttery goodness, and butter is nearly always the right decision, so if you can handle the additional steps, I say go for it.

Oat Wheat Tart Crust
1 cup rolled (oops! couldn’t find these, so I used 1 c. wheat flour)
½ cup whole-wheat flour
1cup all-purpose flour
¼ cup dark brown sugar, firmly packed
1 ½ sticks (¾ cup) cold unsalted butter, cut into cubes
¼ cup milk

1. Normally you would use a food processor to grind up the oats, if you had them, until ground but not powdered. Add the flours, sugar, and salt and pulse until combined. Add the butter and pulse until sandy. Add the milk and pulse a few seconds.

2. Scoop the dough out, form into a large ball, wrap it tightly in plastic wrap and refrigerate for at least 1 and up to 3 hours.

3. Unwrap the dough, put it on a floured work surface, cut into 8 equal pieces. Gently shape each into a smooth disk (dough will be sticky), and then slide onto floured parchment paper and refrigerate for ten minutes (I skipped this). Using a floured rolling pin, roll the disks into a 6-inch, ¼-inch thick rounds, and place gently into tartlet pans, pushing gently against the sides and rolling down or trimming any excess.

4. Preheat oven to 325 degrees F, and put the tartlet crust into the freezer for 30 minutes. Place on a baking sheet and bake, rotating halfway through, for about 15 minutes or until the crusts are golden brown. Transfer to a rack, and let cool while you make the pudding. Remove shells from pans once they are cooled.

“Butterscotch” Pudding
6 large egg yolks
¾ cup granulated sugar
¼ cup water
¼ cup heavy cream
½ cup dark brown sugar, firmly packed
1/3 cup cornstarch, sifted (tapioca starch would work a-okay too)
1 teaspoon salt
3 cups whole milk
1 vanilla bean
1 Tablespoon unsalted butter
2 Tablespoons whiskey (or you know, more than that)

1. Put egg yolks into heatproof bowl and set aside. In a small saucepan, combine white sugar and water and stir over medium heat until the sugar is dissolved, then increase heat to medium high and cook until mixture turns dark amber. Swirl the pan if necessary to distribute the color evenly, but do not stir. Remove form heat, let stand 1 minute, then stir in the cream. Pour into a small bowl and set aside.

2. In another small saucepan, combine brown sugar, cornstarch, and salt. Stir in milk, and whisk to combine. Split the vanilla bean lengthwise, and scrape out the seeds into the saucepan; toss in the bean husk. Cook over medium-high, whisking occasionally until the mixture comes to a boil. Remove from heat and add the caramel, whisking until combined, then pour one-third of the mixture over the eggs. Keep whisking and add another third, then transfer the egg mixture back to the pan with the milk mixture in the saucepan, and bring to a boil over medium-high. Boil 2 to 3 minutes.

3. Remove from head and add butter and whiskey. Keep whisking for about a minute to cool then let pudding sit for 15 minutes. Remove vanilla beans. Whisk pudding again until smooth, and divide into shells evenly, saving just a couple tablespoons in a separate bowl. Cover the tarts and bowl with plastic wrap, and chill in fridge for 2 hours. Before serving, whisk the pudding in the bowl, and add a dollop to each tart. Top with some chocolate-covered espresso beans, and you’re all set!