Preheat oven to 325°F. Grease a 2-quart baking dish. In a small saucepan over medium heat, cook cherries and brandy until simmering; remove from heat and set aside.
In a saucepan, bring cream, milk, 1/2 cup sugar and salt to a boil. Remove from heat and stir in chocolate to melt.
Whisk eggs, yolks and remaining 1/2 cup sugar. Whisk in 1/3 chocolate mixture slowly and then remaining mixture and vanilla to finish custard.
Layer baking dish as follows: 1/3 of brioche, 1/2 cherries, another 1/3 brioche, remaining cherries (and brandy) and remaining brioche. Pour custard on top to soak brioche.
Place bread pudding dish in a larger dish or pan and pour enough hot water into larger pan to come 2/3 up sides of pudding dish. Bake until just set and center jiggles slightly, about 1 hour, 10 minutes. Let cool.
Spoon pudding into dishes. Top with whipped cream and shaved chocolate, if desired.