In a large bowl, mix together flour, sugar, salt and cinnamon. Cut butter into cubes, then add to mixture using a pastry cutter or two forks until pea size balls form. Add whiskey, one whole egg and mix again to incorporate.
Knead the dough until it comes together. Flatten into a circular shape, then wrap tightly with plastic and refrigerate for at least 2 hours.
Lightly flour a large, clean surface. Roll out the dough until it's about 1/4" thick. Use a large round cookie cutter and press out circles until all dough is used.
In a large pot over medium heat, add 2-3 inches of cooking oil and heat to 360 degrees F. A deep fryer can also be used.
Wrap a circle of dough around a cannoli tube, bringing together the sides so they overlap. Brush with egg whites to seal. Carefully, using tongs, add one to the hot oil and let cook until golden brown, turning occasionally so it cooks evenly, about 3-4 minutes. Remove and let drain/cool on a paper towel lined baking sheet.
When cool enough to handle, carefully remove the shell from the tube. Repeat this process until all shells are cooked. Allow all shells to cool completely, about 2 hours.
Shave pieces of chocolate into a small bowl and set aside.
Place parchment into a large plastic container.
Take one pint ice cream out of the freezer and let set on counter for about 10 minutes to soften. On a large cutting board, scoop out ice cream and cut into smaller pieces that can be smooshed by hand.
Working quickly, gently press ice cream into the ready shells until filled. Dip each end into bowl of chocolate shavings. Place each frozen cannoli into the lined plastic container, cover and freeze immediately to set. Repeat steps using the second pint of ice cream. Allow all cannoli to refreeze for 2-3 hours.
When ready to serve, remove from freezer and place on a plate, dusting the top with powdered sugar, some whip cream, or more chocolate shavings and enjoy immediately!