Preheat oven to 375°F. Spread 2 tablespoons butter over bread slices. Cut bread into 1-inch pieces. Whisk half and half, eggs, vanilla, and 1/3 cup sugar in large bowl to blend. Add bread cubes, chocolate chips, and dried cherries; toss to coat. Divide mixture among six 2/3-cup custard cups. Dot tops with remaining 1 tablespoon butter. Bake 10 minutes. Sprinkle puddings with 2 tablespoons sugar. Bake until tops are browned, about 15 minutes.
Meanwhile, whisk cream, remaining 1 tablespoon sugar, and kirsch in medium bowl just until slightly thickened. Serve puddings warm with kirsch cream.
