Preheat oven to 325°F. Spray a 9x5-inch loaf pan with baking spray with flour.

For cake: In a small skillet, heat 3 tablespoons bourbon over medium heat until bubbles begin to form. Remove from heat, and add cherries. Let stand for 30 minutes.

In a medium microwave-safe bowl, combine chocolate and butter. Microwave on high in 30-second intervals, stirring between each, until chocolate is melted and smooth (about 1½ minutes total). Add sugar and cherry mixture, stirring until sugar is almost dissolved. Let cool for 10 minutes. Whisk in eggs and milk until smooth. Stir in flour, baking powder, and salt. Pour batter into prepared pan.

Bake until a wooden pick inserted in center comes out clean, about 1 hour and 15 minutes. Let cool in pan for 10 minutes. Poke holes in warm cake, and pour remaining 3 tablespoons bourbon over cake. Let cool in pan for 30 minutes. Remove from pan, and let cool completely.

For glaze: In a small microwave-safe bowl, combine chocolate, cream, and butter. Microwave on high in 30-second intervals, stirring between each, until chocolate is melted and smooth (about 1 minute total). Let stand for 30 seconds. Stir until smooth. Stir in bourbon. (Glaze will thicken as it sets.) Spread glaze over cooled cake. Garnish with cherries, if desired.