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.