Line twenty 2-1/2-inch muffin cups with foil bake cups; set aside. In a medium bowl, stir together flour, cocoa powder, baking powder, baking soda, salt, and cinnamon. Set aside.
In a large bowl, beat the butter with an electric mixer on medium to high speed for 30 seconds. Add sugar; beat until combined. Add eggs, one at a time, beating for 30 seconds after each addition. Beat in chocolate and vanilla. Alternately add flour mixture and milk to chocolate mixture, beating on low speed after each addition until well combined.
Spoon batter into prepared muffin cups, filling each nearly two-thirds full. Bake in a 350 degree F oven for 15 to 18 minutes or until a toothpick inserted near the centers comes out clean. Cool in muffin cups on wire racks for 10 minutes. Remove from pans and cool completely on wire racks.
Place cupcakes 2 inches apart on wire racks set over waxed paper. Spread a scant 1 teaspoon of the preserves over each cupcake.
Slowly drizzle a small amount of the Chocolate Ganache over each cupcake, allowing it to spread and cover the preserves and entire surface of the cupcake. If necessary, spread ganache gently so it covers the preserves completely. Let stand for 20 minutes.
To decorate, fill a decorating bag fitted with a small round tip with Decorating Icing (or, place icing in a resealable plastic bag and snip a small piece off one corner to use as a piping bag). Pipe on a tuxedo (vest, bow tie and buttons) on nine of the cupcakes. Pipe on a dress (necklace, buttons and corsage) on remaining cupcakes. Use small decorative candies to detail the buttons or necklace. Makes 20 cupcakes.
Chocolate Ganache: In a small saucepan, bring 1/2 cup whipping cream just to boiling over medium-high heat. Remove from heat. Chop 7 ounces semisweet chocolate, bittersweet chocolate or milk chocolate. Add to hot cream (do not stir). Let stand for 5 minutes. Stir until smooth. Let stand at room temperature until completely cool but still drizzling consistency before drizzling over the cupcakes. Makes about 1 cup.
Decorating Icing: In a medium bowl, combine 1-1/2 cups powdered sugar and enough milk (4 to 7 teaspoons) to make of piping consistency. If desired, stir in a few drops of food coloring. Makes about 1/3 cup.