In 2010 we moved from Detroit to Chicago during the height of the cupcake craze. Sprinkles was everything to everybody. We certainly ate our fair share of the Beverly Hills phenom, but soon came to realize that Chicago was and always will be a pie town. Pizza pie goes without saying, but Chi-town also has the best sweet pies north of the Mason-Dixon. Much in part due to the arrival of Hoosier Mama Pie Company.
We lived in Wicker Park, close to Hoosier Mama's flagship location in Ukrainian Village. It's a tiny bustling bakery decked out in vintage Americana charm. It's the kind of place you take your out-of-town guests while thinking to yourself, "You have no idea what you're in for."
And what they're in for is "chess" pie. Sure Hoosier Mama excels at the standard American pie playbook—apple pie, blueberry pie, banana cream pie—but it's their Southern (by way of England) chess pies that will have you calling your mama in tears.
While living in Chicago it seemed pointless to learn how to bake my own chocolate chess pie. Hoosier Mama was only 5 minutes away and chef Paula Haney's pies made my feeble attempts at baking look like sugar coated stupid. Now that I'm in Los Angeles—2000 miles to the nearest Chicago—I've been craving a slice of her chocolate chess pie.
And from this distance I must atone. I owe an apology and explanation to Hoosier Mama herself. Paula, if by some slim chance you're reading this, I am sorry for what transpired on the week of September 12th, 2011.
You see, about two weeks prior I stopped in to Hoosier Mama to buy a chocolate chess pie to bring to my family in Michigan. I chatted briefly with Paula about bringing that pie back home to Michigan's Upper Peninsula (locally referred to as the "U.P.")
"You're a Yooper?" Paula asked, summoning the colloquial slang for residents of the Upper Peninsula. "Can you bring me back a really good U.P. pasty?"
A U.P. pasty (pronounced (PASS-tee) is Michigan's version of Cornwall, England's version of Italy's calzone or Spain's empanada. It's a large crusty hand pie traditionally filled with beef, potatoes, turnip or rutabaga, and onions. It's a mainstay of my hometown and nowhere else in America can you get something quite like it. Others have tried, of course. But only ours are so infamous that we've been featured in national news outlets like NPR, Chicago Tribune, USA Today, and others.
That's a lot of pressure! So two weeks later I made the 7 hour drive back from the U.P. to Chicago with a few Lawry's pasties in a cooler; bursting with anticipation to hand deliver our cultural claim to fame to Paula. The baking icon would be so impressed. Little ol' me bringing her the best U.P. pasties, frozen to survive the journey and ready to bake in her professional kitchen.
Wait, what? Back up. Did you say frozen?
Well, duh, how else would a pasty survive the two days until I would see Paula?
So the day after my return trip I walked into Hoosier Mama, heart pounding like a fanboy at a Britney Spears concert. (That reference comes easy, trust me.) I walked up to the counter and asked if Paula was available. I knew she was. I'd already seen the flash of her pink chef's jacket among the ballet of bakers twirling their stainless steel mixing bowls and using their origami sorcery to turn flat cardboard into pie boxes.
"Hi Paula, they just put your pasties in the freezer back there. All you have to do is bake them for 45 minutes."
"Oh, their frozen?" she asked politely, the disappointment palpable.
"Yeah, 'cause it's a long drive from the U.P. They're parbaked so they're still really good frozen" I explained. No, actually I pleaded. All I wanted was your love and approval, Paula!
She, of course, thanked me for the pasties and very sweetly gave me a few free slices of pie. She was no doubt grateful, yet I could tell she'd wanted to try the very best and freshest U.P. pasty. Who could blame her? She's one of the best bakers in one of the biggest cities in America. I mean, she wrote a damn cookbook! She's managed to make a vinegar pie taste incredible!
Gah. Dumb dumb dumb. What was I thinking?
Anyway, in honor of you Paula-who-is-probably-not-reading-this, I made my first chess pie. Actually, it's chess-adjacent, but it's delicious and didn't fall apart so it's still a major victory in this kitchen. And I'm sorry if I disappointed you with my pasty delivery and I hope you enjoyed them nonetheless.
I've gone on long enough so I won't bore you with the history of why a chess pie is called a chess pie. Suffice to say the texture and density of a chocolate chess pie falls somewhere between a brownie, a custard pie, and a pecan pie.
Because there aren't a lot of ingredients, good quality ingredients should be used to bring out the best flavor. My recipe isn't heavy on sugar so it doesn't use sweetness to mask a nasty cheap cocoa like Hershey's. It uses super delicious cultured vegan butter, farm fresh eggs, and organic yogurt. At Hoosier Mama they don't use yogurt, I believe they use chopped bittersweet chocolate, and they use cornmeal instead of flour. Hence the recipe below is chess-adjacent and not exactly a true chess pie. It's a simple homey tasting pie that has a great texture and doesn't clobber you with sugar or other trickery.
Sometimes it takes a village. Along with consulting the Hoosier Mama recipe, below are the two recipes I combined to develop this chocolate walnut chess-adjacent pie. I came up with some alterations, but I must give credit to the talented home bakers who shared great tips in the comments sections, especially panamabev. But I think the most credit goes to our chickens for laying such beautiful eggs and not even getting to taste the fruits of their labors. Is that weird to say?