If you’re not familiar with Millionaire’s Shortbread, please allow me to explain.
The traditional version of these brilliant cookies marries buttery shortbread, gooey caramel, and rich chocolate into an almost sinful bite of heaven. These cookies truly are such stuff as dreams are made on; I’m pretty sure Shakespeare was eating Millionaire’s Shortbread while writing The Tempest. For realz.
Millionaire’s Shortbread is typically made tray-bake style (i.e. bake the cookies in a large baking dish, spread the caramel over the cooled cookies, smear with melted chocolate, then slice into bars once set). My version adapts the Millionare concept to an assembly method conducive to individual cookies rather than bars.
Since shortbread is SUCH a rich, heavy cookie, Millionaire’s Shortbread is usually cut into very small bars. I chose my light and fluffy Tom’s Favorite Sugar Cookies to serve as the vehicle for the caramely-chocolatey topping. Why? Allows for bigger cookies without tummyaches 🙂
I’ve made batches of these cookies with milk chocolate and with dark chocolate, and both are excellent! I’m a dark chocolate girl by rule, but there’s something about a milk chocolate-caramel combo (Rolos, anyone?), so, honestly, just use whichever chocolate type you prefer. Even white chocolate would be delish!
While these barely-sweet sugar cookies are perfect (in my opinion) as is, or delicately topped with a thin citrus glaze, they lend themselves just as well to a more decadent garnish. A fine sprinkling of kosher salt keeps these cookies classy and prevents them from being overwhelmingly sweet.
It’s alright if the caramel stays on the gooey side, since the chocolate will form a protective shell over the top, so they can be easily stored in layers once set. I actually don’t like a perfectly smooth chocolate smear on top; I like the character conferred to each cookie by an endearing little mountain or drizzle here and there. Don’t you wish that you had a protective chocolate shell to keep you safe, too? A chocolate security blanket — that would be true happiness!
4 ounces good quality milk or dark chocolate (whichever you prefer!)
Kosher salt, for sprinkling
Make/bake cookies: In a medium-sized mixing bowl, place softened butter, powdered sugar, granulated sugar, and oil (in that order!), and beat until very pale and creamy. Beat in egg and vanilla. In a large measuring cup or small mixing bowl, use a fork to combine and aerate flour, baking soda, cream of tartar, and salt. With mixer on low, gradually add dry ingredients to wet. Cover mixing bowl, and chill 1 hour.
Preheat oven to 350 degrees farenheit. Line a baking sheet with parchment paper or a silicone baking mat. Roll 1″ balls, and space ~1 1/2″ apart on cookie sheets. Gently press down one dough ball with the bottom of a small diameter drinking glass to get some of the oil on the bottom of the glass. Then, dip the glass in a shallow bowl containing the 1/3 cup granulated sugar + 1/8 teaspoon salt (the sugar/salt should now stick to the bottom of the glass). Use the sugared/salted glass bottom to flatten the center of each dough ball to ~1/4″ thick, re-dipping in the sugar/salt mixture between each cookie. The goal is to leave a depression in the middle of each cookie, with a raised edge all the way around (exaggerate the depth of the depression at this stage, since baking will reduce the depth due to in-oven puffing…an accepted scientific phenomenon). Bake 9-10 minutes, rotating sheet halfway through bake time. Let sit on baking sheet 3 minutes to deflate, then remove cookies to wire racks to cool completely.
Become a millionaire: As cookies are cooling, make the caramel sauce. In a 2-cup microwave-safe measuring cup, combine unwrapped candies, butter, and milk. Microwave 1 minute, stir, then microwave in increments of 10 seconds, stirring vigorously between, until caramels have completely melted and mixture is smooth. Set aside to cool to room temp.
Lay down a sheet of wax paper under your cooling racks to facilitate clean-up following cookie assembly. Spoon ~1/2 – 1 tablespoon of your caramel sauce into the depression in each cookie — you will have some dribbles down the sides…it’s only human. Let set for 20 minutes (or carefully transfer to fridge for 10 minutes). Meanwhile, chop up chocolate and place half of it in a microwavable zip-top bag or microwavable measuring cup. Microwave for 30 seconds (with bag UNZIPPED, if using), flip bag over (or stir in measuring cup), and continue to microwave in 5 second increments, flipping/stirring between, until completely smooth. Chocolate burns easily, so stick to small heating increments. Once melted, if using the bag-method, snip off a corner and distribute chocolate over cookies, six at-a-time, and use an offset spatula to spread the chocolate into a smooth layer, and sprinkle with kosher salt. Repeat until chocolate has been exhausted. If not using the bag-method, you can either transfer the melted chocolate to a pastry bag to divide the chocolate between the cookies (again, six at-a-time to prevent setting before spreading), or spoon the chocolate directly onto the cookies (the spoon method tends to be a little messier for me, but you may possess better coordination than me). Repeat with the remaining half of the chocolate to frost and salt the remaining cookies. Let sit on racks until chocolate has completely set. Cookies may be stored in the fridge or at room temp, with wax paper between layers, in airtight containers.