In a large, microwave safe bowl, combine the chopped chocolate, unsalted butter, and 1/4 cup of red wine. Loosely cover and microwave for 30 seconds. Stir and continue to microwave and stir in 15 second intervals until the chocolate is completely melted and the mixture is smooth.
While still hot, mix in the sugars and stir to dissolve. Allow the batter to cool for a couple of minutes, and then mix in the egg, egg yolk, and vanilla extract.
Once well-combined, fold in the flour, cocoa powder, and salt, until no white streaks or clumps remain. Be careful not to overmix.
Pour the brownie batter into an 8 inch cast iron skillet and smooth with the back of a spoon so that the batter is even. Bake until cooked through but still soft, about 18-20 minutes.
While the brownie bakes, make the hot fudge. In a smaller microwave safe bowl, combine the heavy whipping cream, red wine, and dark chocolate. Loosely cover and microwave for 30 seconds. Stir and continue to microwave and stir in 15 second intervals until completely melted and smooth. While still hot, mix in the light brown sugar. Set aside.
When the brownie is ready, top it with vanilla ice cream and berries and drizzle with the red wine hot fudge. Serve warm.