Arrange oven racks so one is in top third of oven and other in bottom third. Preheat oven to 350°F Line two large baking sheets with parchment paper.
In heatproof bowl set over a saucepan of simmering water, melt chocolate. Remove bowl from saucepan. Cool for 10 minutes. Meanwhile, in bowl and using electric mixer, beat butter and sugar on medium-high speed until crumbly. Add eggs one at a time, beating well after each addition. Beat 1 minute longer. Scrape side and bottom of bowl; beat another 30 seconds or until mixture is very pale and creamy. Using wooden spoon, stir in cooled chocolate and vanilla until streaky. Before completely mixed in, stir in flour, cocoa and baking powder just until combined. Stir in cherries and vanilla chips.
Drop in aprox. 1 tbsp. balls onto prepared baking sheets, spacing well apart. Bake both pans at once, one in center of oven and the other on bottom third of oven, for 9 to10 minutes, switching the pans half-way, or until crackled on top but not firm to the touch. Cool cookies on baking sheets for 2 minutes before transferring to wire rack to cool.
