For the ice cream:
To candy the bacon, preheat the oven to 400F (200C).
5 strips bacon
Lay the strips of bacon on a baking sheet lined with a silicone mat or aluminum foil, shiny side down.
About 2 tablespoons light brown sugar
Sprinkle 1 1/2-2 teaspoons of brown sugar evenly over each strip of bacon, depending on length.
Bake for 12-16 minutes. Midway during baking, flip the bacon strips over and drag them through the dark, syrupy liquid that's collected on the baking sheet. Continue to bake until as dark as mahogany.
Remove from oven and cool the strips on a wire rack.
Once crisp and cool, chop into little pieces.
3 tablespoons (45g) salted butter
To make the ice cream custard, melt the butter in a heavy, medium-size saucepan.
3/4 cup (packed) brown sugar (170g), light or dark
2 3/4 (675ml) cup half-and-half
Stir in the brown sugar and half of the half-and-half.
Pour the remaining half-and-half into a bowl set in an ice bath and set a mesh strainer over the top.
3 large egg yolks
In a separate bowl, stir together the egg yolks; gradually add some of the warm brown sugar mixture to them, whisking the yolks constantly as you pour.
Pour the mixture back into the saucepan.
Cook over low to moderate heat, constantly stirring and scraping the bottom with a heatproof spatula, until the custard thickens enough to coat the spatula.
2 teaspoons dark rum or whiskey
1/4 teaspoon vanilla extract
Optional: 1/4 teaspoon ground cinnamon
Add liquor, vanilla and cinnamon, if using.
Chill the mixture for about 5 hours.
Once thoroughly chilled, pour into ice cream maker. Add the bacon bits during the last moment of churning, or stir them in when you remove the ice cream from the machine.
For the chocolate chip cookies:
Heat oven to 375 degrees Farenheit.
2 sticks unsalted butter
Melt the butter in a heavy-bottom medium saucepan over low heat.
2 1/3 cups flour
1 teaspoon kosher salt
1 teaspoon baking soda
Sift together the flour, salt, and baking soda and put aside.
1/4 cup white sugar
1 1/4 cups brown sugar
Pour the melted butter in a mixer's work bowl. Add the sugar and brown sugar. Cream the butter and sugars on medium speed.
1 egg yolk
2 tablespoons milk
1 1/3 teaspoons vanilla extract
Add the egg, yolk, 2 tablespoons milk and vanilla extract and mix until well combined.
Slowly incorporate the flour mixture until it is thoroughly combined.
2 cups [semisweet] chocolate chips
Stir in the chocolate chips.
Chill the dough.
Scoop onto parchment-lined baking sheets, 1 inch balls.
Bake for about 13 minutes, checking the cookies after 5 minutes. Cookies for ice cream sandwiches should be slightly underbaked so that they remain chewy when confronted with the coldness of the ice cream. The chewiness will also make them hold the weight of the ice cream without breaking. The 1 inch ball of dough should also produce a thick enough cookie so that the cookie is sturdy.
Rotate the baking sheet for even browning.
Cool completely and store in an airtight container.
Creating the ice cream sandwiches:
After cookies are cooled to room temperature, bring ice cream out of the freezer for scooping (ice cream should be at about -5 degrees F, or as frozen as possible).
Scoop 3.5 oz of ice cream onto a cookie on a half tray, face down.
Place second cookie on top. Push down slightly, but not too hard, as to not push the ice cream out of the sides or break either of the cookies.