It's a well-known fact around the Food52 office that if Amanda Hesser sits you at the center of her dinner party table it's because you're funny (or at least more funny than the people way down at the end).
And if that holds true for where desserts land on the table (and I have to believe it does), here's the guy bound to be the life of the next big party where cake is present (cough, Thanksgiving, cough).
If pumpkin pie is the second cousin you're obligated to invite but spend the day avoiding, and pecan pie is the hot-breathed great auntie who's always a little too close for comfort, and grape salad is the guest who might not even exist, then this cake is the wacky uncle: easy-going, conversation-starting, slightly mysterious, and enjoyable in large doses.
What's intriguing, for starters, is the cake's up-in-the-air identity. With a sugar cookie-like crust that's made in the food processor and pressed into the pan, it's much less finicky than pie. Adding an egg to the dough not only gives you a base that's crispy in some places and puffy in others, but it also frees you from concern over whether your dough will be flaky.
For the cobbled top, all you have to do is pinch off bits and pieces of the second piece of dough and scatter them over the top of the cake; in the oven, they'll spread and rise into crumby knobs that push the dessert towards the cake side of the cake-pie spectrum.
But perhaps the wackiest, weirdest part of the cake—even more so than its split identity—is that it's filled with chunks of butternut squash that have been roasted with orange, olive oil, cardamom, and the teeniest amount of brown sugar and honey. Perforated by chunks of a vegetable that's flavored just as often with cayenne as it is with maple syrup, the cake tightropes between savory and sweet.
So it's neither a pie nor a cake. And it's neither a dessert nor... okay, it's a dessert. But there are vegetables in the ingredient list!
Just think of it as a lovable weirdo. Embrace its eccentricity. And if you want something sweeter, add a couple additional tablespoons of honey or brown sugar.
The recipe for the dough comes from Nanny's Rosh Hashanah Apple Cake, "Nanny" being the great-grandmother of Saveur's Jake Cohen. I don't know Jake, but I'd like to invite him and his cake to my family's Thanksgiving table, where they'll both be seated towards the center.
Serves 8 to 10
Adapted from Nanny's Rosh Hashanah Apple Cake
For the pie-cake:
2 cups (9 ounces) all-purpose flour
1 cup (7 ounces) sugar
1 teaspoon baking powder
1/2 teaspoon kosher salt
2 sticks chilled unsalted butter, cut into 1/2-inch cubes
1 large egg, lightly beaten
For the roasted squash filling:
2 pounds peeled and cubed butternut squash (1/4- to 1/2-inch cubes)
2 tablespoons brown sugar, divided
Zest and juice of 1/2 orange
1 tablespoon honey
1 tablespoon olive oil
1 teaspoon cardamom
1 small pinch salt
1/3 cup chopped toasted hazelnuts
Photos by James Ransom