Cherry and chocolate make a winning combination in this dessert treat. You can bake the phyllo cups up to 3 days in advance and store them in an airtight container.
Preheat oven to 350 degrees. Mix together cinnamon and 2 tablespoons sugar. Lay 1 sheet phyllo on a work surface (cover remaining sheets with a damp towel). Brush phyllo with butter; sprinkle with cinnamon-sugar. Layer 2 more sheets on top, brushing each with butter and sprinkling with cinnamon-sugar.
Cut stacked phyllo into 6 rectangles and gently press each into a standard muffin cup, pleating as needed so phyllo sits flat in bottom of cup. Bake until phyllo is golden brown, about 12 minutes, rotating pan halfway through. Let cool completely in pan on a wire rack.
Meanwhile, toss cherries with 1 tablespoon sugar and let sit until cherries have released some juice, 10 minutes. Combine 3 tablespoons sugar, ricotta, and vanilla; fold in chocolate. Divide mixture among phyllo cups and top with cherries.
There are about 30 sheets of phyllo per package. To use just a few, cover the sheets as you work, so they don't dry out; wrap remaining phyllo in plastic and refreeze for later.