I think I was in the second grade when I learned about whoopie pies. Every week we had a "craft day" where one of the moms volunteered to come in and work with the class to make a hands on project. Thankfully my mom was too busy working her day job to worry about this sort of thing, so I was spared parental embarrassment and she was saved from stressing about what to demonstrate to the kids. I do remember learning some cool things though. I definitely brought home a paperclip necklace and have a vague memory of poking myself with wires to make some hippie burlap flower. I glued together a puffy red felt heart pillow which I soaked in perfume and gave to my grandmother.
Above all, I remember whoopie pie day. I remember the moist chocolate cakes filled with cream (they looked like a hamburger but were dessert—genius.) It made some lucky kid's mom a total hit with the class. These cakes mostly stuck in my mind because of their questionable name. Why was it called a whoopie pie? Was it meant to resemble that thing which you sat on to make a fart sound? It did look like a squishy cushion. But then again, there was also that song "feel like makin' whoopee", that I'd heard, and which I could only presume had something to do with sex—though I wasn't exactly sure how that related to cake. I was seven, I was confused, and it took many years before I could say "whoopie pie" without giggling.
Be it the goofy name or that fact that it's a handheld treat which, like cupcakes, lends itself to limitless variations, whoopie pies are still a hot product. But instead of trying to woo you by adding another far out flavor combination to the list, I chose to keep my recipe classic with a chocolate-on-chocolate version. The cake-y cookie is based off of a recipe that I made every week at my bakery, simple and straight forward. For the cream, I've never filled my whoopie pies with either whipped cream or a sugary, quick butter frosting. I always make the one that reminds me of my very first: a cooked cream filling made from heating milk and flour until thick, then whipping it up with sugar and vegetable shortening until it reaches ridiculously light and fluffy heights.
Even though I'm a firm believer in the original version from my memories, I respect that vegetable shortening in a cream filling is not for everyone. So as well as making the filling chocolaty with cocoa and melted chocolate, I swapped out most (not all!) of the shortening for butter. The resulting cream is a little more vulnerable to melting sans shortening, but I won't complain one bit about the buttery flavor.
About the Author: Yvonne Ruperti is a food writer, recipe developer, former bakery owner, and author of The Complete Idiot's Guide To Easy Artisan Bread. You can also watch her culinary stylings on the America's Test Kitchen television show. She presently lives in Singapore as a freelance writer for Time Out Singapore. Check out her blog: shophousecook.com . Follow Yvonne on Twitter.