Place an 11-inch, high-sided skillet or saute pan over high heat. Add half the pears and 1/3 cup sugar. Cook, stirring occasionally, until pears are soft and just beginning to turn golden, 12 to 20 minutes (cooking time will vary depending on the type of pears and their ripeness). Remove skillet from heat, and transfer pears to a large bowl to cool. Repeat process with the remaining pears and 1/3 cup sugar.
Preheat the oven to 350 degrees. Melt butter in a small saucepan set over medium heat, stirring occasionally. Whisk in cinnamon and remaining 2 tablespoons sugar, and set aside.
Cut the crusts from the bread. Cut each slice into three 1-by-2 1/4-inch strips. Discard the scraps, or save for making breadcrumbs. Generously brush one side of the bread strips with the butter mixture. Leaving the bottom open, line the sides of the jumbo muffin-tin cups with overlapping pieces of bread, with the buttered side facing out, against the tin, pressing as you go.
Pack about 1 cup pear mixture into each muffin tin, making sure the pears are flush with the top of the tin and the bread slices. Place the tins in the oven, and bake until the bread is golden brown on the outside, about 20 minutes. Transfer the muffin tins to a wire rack to cool for 10 minutes. Unmold the charlottes by inverting onto a baking sheet or cutting board. Serve immediately with vanilla bean creme anglaise and blackberry compote.