I Tried Frank Sinatra’s Favorite Pumpkin Pie Recipe, and It’s Nostalgic Flavor Took Me Back in Time

I love reading through old recipes. I’ve been known to stop and peruse church cookbooks at garage sales, and my mom and I are slowly working our way through my great-aunt’s collection of family recipes (one of these days, we swear we’ll finally tackle the figgy pudding!)

So, when I stumbled upon a recipe for Frank Sinatra’s favorite pumpkin pie, I was intrigued. The recipe was first published by Nancy Sinatra in a booklet called “Desserts Frankie Loves” in 1945 and has recently been getting buzz online. It’s an old-fashioned take on pumpkin pie that uses molasses—which, for a time, was the most popular sweetener in America—in place of the sugar used in most modern recipes.

Many pumpkin pie recipes today are flavored with a pre-mixed pumpkin pie spice (or a homemade mix of nutmeg, cinnamon, ginger, cloves, and sometimes allspice), but Nancy’s self-described “spicy” pumpkin pie is seasoned simply with cinnamon and ginger. And in keeping with the times, the homemade pie crust also calls for shortening in place of butter. This recipe is quite different from the pumpkin pies I’ve been making for years, and I couldn’t wait to give it a try.

How to Make Frank Sinatra’s Favorite Pumpkin Pie

If this recipe was good enough for Ol’ Blue Eyes, I figured it would be good enough for me. Here’s how to make it:

1. Make the crust. In a mixing bowl, combine sifted flour and salt, then use a knife to cut in half of the cold shortening until it resembles small pebbles. Add the remaining shortening and cut into mixture again. One tablespoon at a time, add cold milk, bringing the dough together with a fork. Shape the dough into a disc, cover it in plastic wrap, and refrigerate for at least 30 minutes. After the dough has chilled, roll it out to fit a shallow 9-inch pie plate. Transfer dough to pie plate, flute edges, and use a fork to poke holes in the bottom of the dough. Bake pie crust at 425°F for 10 minutes before adding filling.
2. Make the filling. In a large mixing bowl, combine pumpkin, molasses, cinnamon, ginger, salt, and egg and mix until thoroughly combined. Slowly stir in milk until it’s fully incorporated into the rest of the filling.
3. Assemble, bake, and let chill. Pour filling into partially baked pumpkin pie crust. Bake at 350°F for 45 minutes, or until a knife inserted in the center of the pie comes out clean. Transfer to a cooling rack and let cool to room temperature, about 1 hour. Cover pie with plastic wrap and let chill in refrigerator for at least 4 hours before serving.

Tips for Making Pumpkin Pie

• If you’re not a fan of shortening, you can substitute butter, or even use another pie crust recipe altogether.
• Like many custard pies, this recipe calls for a par-baked crust, which means you will partially bake the crust before adding the filling. Doing so ensures that the crust will finish baking at the same time as the filling and prevents a soggy bottom.
• You can really taste the molasses in this recipe, which you might either love or hate. If you’re not a fan of molasses, you can also sub in an equal amount of maple syrup. If you stick with the molasses, opt for a light molasses, which has a sweet, delicate flavor.
• Nancy’s recipe calls for a shallow 9-inch pie pan, which was the standard in home kitchens when this recipe was written. If possible, stick with a shallow pie pan instead of a deep-dish pie pan.

The Verdict on Frank Sinatra’s Pumpkin Pie

From the shortening in the homemade pie dough to the strong molasses flavor of the filling, this recipe took me back in time. I’d recommend it for any bakers who are interested in trying out old-fashioned recipes, though it’s worth noting that it might taste a lot different than the pumpkin pie you’re used to. The recipe itself was simple to make, though the pie dough wasn’t my favorite, as the thin, sticky dough shrunk down significantly in the pan. Next time, I’d probably opt for my favorite all-butter pie crust recipe instead. That said, this is still a beginner-friendly yet tasty pie to add to your Thanksgiving spread.