Heat oven to 350ºF (325°F. for dark cookie sheet). In large bowl, break up cookie dough. Stir or knead in cocoa and melted chocolate until well blended. Stir in cherries. Cover; freeze dough 30 minutes for easier handling.
Place paper cups on ungreased large cookie sheet. Shape dough into 36 (1-inch) balls; place each in paper cup.
Bake 11 to 17 minutes or until puffy and surface loses its shine. Immediately remove cookies in cups from cookie sheet; place on wire racks. Cool completely, about 15 minutes.
In 1-quart saucepan, heat 1/2 cup chocolate chips and condensed milk over low heat about 3 minutes, stirring constantly, until chips are melted and smooth. Stir in brandy. Drizzle about 1 teaspoon icing over top of each cooled cookie.