1. Heat oil in a deep pot over medium heat until it registers 370 to 375 degrees on a deep-fat fry thermometer.
2. Mix cornmeal, 1/3 cup of the flour, the pepper, cayenne and salt in a large resealable plastic bag.
3. Whisk milk and egg together in a medium bowl.
4. Cut pickles into spears (about 8 per pickle). Blot dry on paper towels and toss in a bowl with remaining 1/2 cup flour.
5. Dip 8 to 10 spears in egg mixture, then add to bag with cornmeal mixture. Shake to coat pickles. Spread spears onto a rack and continue with all spears (in batches of 8 to 10).
6. Fry one batch of pickles for 3 minutes until golden. Transfer to a paper towel and repeat with all batches, returning oil to 375 degrees before adding each batch. Serve with ranch dressing.