Preheat oven to 375 degrees. Toss cherries with olive oil and salt, then place on a baking sheet and roast for 25 minutes, tossing once or twice during roasting. Let cool. Can be prepared in advance.
Hot Fudge
Bring cream, corn syrup, sugar, cocoa, salt and half of chocolate to a boil in a small saucepan over moderate heat, stirring, until chocolate is melted. Reduce heat and cook over low boil, stirring occasionally, 5 minutes, then remove from heat. Add butter, vanilla and remaining chocolate and stir until smooth. Cool sauce to warm before serving. Sauce can be made 1 week in advance and cooled completely, then chilled in an airtight container or jar. Reheat before using.
Milkshakes
To make milkshakes, combine ice cream, milk, bourbon and cherries in a blender and puree until smooth. Drizzle hot fudge over the inside of each glass, then pour milkshake into glass. Top with whipped cream and cocoa nibs or mini chocolate chips.