To make the ice cream, in a medium bowl, whisk together sweetened condensed milk, vanilla, Bailey's Irish Cream, and salt. Set aside.
In a large bowl, beat whipped cream with an electric mixer until stiff peaks form, approximately 2 minutes. Fold approximately 1 cup of the whipped cream into the Bailey's Irish Cream mixture until combined. Fold the Irish cream mixture back into the whipped cream until well combined.
Pour the mixture into a metal loaf pan and cover with plastic wrap. Freeze for 5 hours.
To make the brownie, melt butter and 8 oz chopped dark chocolate over medium-high heat in a medium saucepan, stirring well. Remove from heat and add to a large bowl. Let cool for 10 minutes.
Preheat oven to 350 degrees F. Lightly grease a 10 to 11 inch cast iron skillet with butter.
Whisk sugar into the chocolate mixture. Add eggs, vanilla and whiskey, whisking until combined. Fold in flour, cocoa powder and salt. Once well-combined, fold in chocolate chips.
Add batter to the skillet. Bake for 30 minutes, until a toothpick when inserted in the center comes out clean. Remove from oven.
Serve with scoops of Bailey's ice cream on top. Top with Bailey's Hot Fudge, if desired, and powdered sugar.