Cherry-Vanilla Brioche Pudding

Bring the maple syrup and the star anise to a boil in a large heavy-bottomed saucepan over medium-high heat and cook until a candy thermometer registers reads 240°F (116°C). (If you don’t have a thermometer, you can use this test to determine whether the temperature is right: Dip a fork in the mixture and let it drip on your work counter; at 240°F (116°C), once cooled, the sugar droplets should be somewhat gummy and firm, not sticking to your finger when you touch them lightly.)

Gradually whisk in the cream. Once incorporated, add the milk and heat to just under a boil. Meanwhile in a medium bowl, briskly whisk together the egg yolks, whole egg, and the salt for 1 minute. Slowly whisk some of the hot cream into the egg mixture to warm it. Gradually pour the warmed egg mixture into the hot cream mixture, whisking the cream constantly as you pour.

Cook over medium heat, continuously stirring and scraping the bottom with a rubber spatula or wooden spoon, until the custard thickens enough to coat the back of a spoon. Strain through a fine-mesh strainer into a bowl to remove the star anise. Set the bowl in a larger bowl of ice to cool it to room temperature, then refrigerate for at least 2 hours and up to 2 days before churning.

Churn the custard in an ice-cream maker according to the manufacturer’s instructions. The ice cream is finished once it has increased in volume and holds the line of the stirring mechanism. It should mound like softly whipped cream. At this point, you must freeze the ice cream for 4 hours to attain a scoopable consistency. It is best served the day it is churned but will keep for up to 1 week in the freezer.

Using a cherry pitter, remove the pits from the cherries.

Run a paring knife down one of the vanilla beans to split it and scrape the seeds into a medium heavy-bottomed saucepan and then toss in the pod as well. Add the port and sugar, bring to a simmer, and cook for 5 minutes. Add the pitted cherries, bring to a boil, then reduce the heat to a simmer and cook for 10 minutes, making sure to stir the mixture gently 2 or 3 times. Pour the compote into a bowl and nestle it inside a larger bowl filled halfway with ice until cool. (The compote will keep in an airtight container in the refrigerator for up to 3 days.)

Preheat the oven to 350°F (175°C).

Trim the hard brown crusts from the brioche and cut each slice into about 6 rectangles, each measuring 1 1/4 by 1 1/2 inches. Lay these rectangular pieces of bread on a baking sheet and drizzle the melted butter over them. Bake until the rectangles are a golden brown. Set aside. Reduce the oven temperature to 275°F (135°C).

Combine the cream and milk in a small heavy-bottomed saucepan. Slit open the remaining vanilla bean and scrape all the tiny seeds into the pan. Add the scraped pod and set over medium-high heat. When the cream is almost boiling, remove from the heat and cover for 20 minutes to steep the mixture.

Meanwhile, in a medium bowl, whisk together the sugar, salt, egg yolks, and whole eggs. Slowly whisk some of the hot liquid into the egg mixture to warm it. Gradually pour the warmed egg mixture into the hot cream mixture, whisking the cream constantly as you pour. Set aside. Remove the vanilla pod. (You can wash, dry, and reserve it for another use.)

You can bake this pudding in one 6-by-9-inch baking dish or in 6 individual ramekins. With the softened butter, slick the dish(es) you are using.

If baking the pudding in a single dish, spread the toasted bread over the bottom. Pick out about 1/3 of the cherries from the compote and intersperse them among the pieces of bread. Pour the warm custard over everything and leave the dish on the counter for 10 to 15 minutes, letting the bread soak up the custard. Bake until any bread chunks sticking out from the top are crispy and brown, 30 to 40 minutes. The center should not jiggle separately from the outside of the custard. If you push a piece of bread down in the center, it should have a very slight spring to it.

If baking the pudding in individual ramekins, place 3 pieces of toasted bread in the bottom of each ramekin. Use 3 bread cubes to line the sides. Set 3 cherries in the center of each ramekin and top the cherries with one final cube of toasted bread. Pour the warm custard over the top to fill the ramekins. Bake for 20 to 25 minutes.

Let the pudding cool slightly before serving.

Serve the bread pudding warm. If you make it early in the day, reheat it in a preheated 300°F (150°C) oven for 10 minutes. If you have baked it in a large baking dish, simply serve a portion on a plate with the cherry compote and a scoop of maple-star anise ice cream. If you are serving ramekins, pour some compote over the bread pudding and serve the ice cream on a side plate. You can also remove the pudding from the ramekins and serve on a plate with the cherry compote and ice cream.