Cinnamon Bread Pudding & Cheesecake Recipe

Prepare crust

Preheat oven to 350°F (175°C). Lightly grease a 9-inch springform pan or a deep 9-inch pie dish. Combine the finely crushed chocolate sandwich cookies, melted butter, and 1 teaspoon granulated sugar in a bowl and mix until the crumbs are evenly coated and hold together when pressed.

Press the crumb mixture evenly into the bottom (and about 1/2 inch up the sides if using a springform) to form a compact crust. Chill in the refrigerator while you prepare the fillings for about 10 minutes to set.

If you prefer a firmer crust, bake for 8 minutes, then cool 10 minutes before filling. Otherwise proceed chilled.

Prepare bread

Tear the day-old brioche or challah into 1-inch pieces and place in a large bowl. Drizzle with 2 tablespoons melted butter and toss gently to coat the pieces evenly.

Make custard

In a separate bowl, whisk together the whole milk, heavy cream, 3 large eggs, 2/3 cup granulated sugar, 1/4 cup packed light brown sugar, 2 teaspoons ground cinnamon, 2 teaspoons vanilla extract, and 1/4 teaspoon salt until the sugars are fully dissolved and the mixture is smooth.

Pour the custard evenly over the buttered bread pieces. Gently press down so most bread absorbs the liquid but avoid mashing. Let sit 10 minutes to soak, then give a gentle stir to distribute custard. If some dry bits remain, let soak an additional 5 minutes.

Spoon or layer the soaked bread pudding mixture over the chilled (or pre-baked) Oreo crust, spreading evenly but leaving about 1/2 inch clear at the edge if you want a rim visible.

Make cheesecake filling

In a medium bowl, beat the room-temperature cream cheese until smooth and free of lumps (use a hand mixer or whisk). Add 1/3 cup powdered sugar and mix until combined. Add 1 large egg, 2 tablespoons sour cream, and 1 teaspoon vanilla extract and beat just until smooth and homogenous. Do not overmix.

Drop tablespoon-sized dollops of the cheesecake mixture evenly over the top of the bread pudding layer. Using the back of a spoon or an offset spatula, gently swirl the cheesecake dollops into the top of the bread pudding to create a marbled pattern; avoid fully mixing—aim for visible cheesecake ribbons and pockets.

Place the assembled pan on a baking sheet (to catch any spills). Bake in the preheated 350°F (175°C) oven for 35–45 minutes, or until the cheesecake swirls are set and the bread pudding is puffed and golden and a thin knife inserted into the center comes out mostly clean with a few moist crumbs. If the crust was not pre-baked and looks underdone, allow an extra 5–8 minutes.

Remove from the oven and let cool on a wire rack for 20–30 minutes. The pudding will settle as it cools. For firmer slices, chill in the refrigerator for at least 2 hours or up to overnight.

Make sauce

While the pudding bakes or cools, prepare the blueberry sauce. In a small saucepan combine 1 cup blueberries, 1/4 cup granulated sugar, 2 tablespoons water, and 1 teaspoon lemon juice. Stir to combine.

Bring mixture to a gentle simmer over medium-low heat, stirring occasionally. In a small bowl, whisk the 1 teaspoon cornstarch with an additional 1 teaspoon water to make a slurry; stir the slurry into the simmering blueberries and cook 1–2 minutes until the sauce thickens and the berries begin to break down but still hold some shape.

Remove from heat and let cool. If you prefer a smooth sauce, mash slightly with a spoon or pulse briefly with an immersion blender; otherwise leave it chunky. Cool to warm or room temperature before serving.

When ready to serve, slice the cinnamon bread pudding & cheesecake. Spoon warm or chilled blueberry sauce over each portion. Dust with powdered sugar and add a dollop of whipped cream if desired.

Store leftovers covered in the refrigerator for up to 3–4 days. Reheat gently in a low oven (300°F / 150°C) until warm, or microwave short bursts on a plate for single servings.