In a blender, combine ice cream, heavy cream, caramel, bourbon and salt. Blend until thick and well-combined. Add more cream, a splash at a time, if too thick. Add more ice cream if too thin.
Drizzle caramel sauce in an abstract pattern inside of glasses. Fill glass with the milkshake. Drizzle with additional caramel on top. Garnish with a wooden skewer with popcorn.