Start off by making your jack Daniels glaze. In a medium sized mixing bowl add the ketchup, Jack Daniels, brown sugar, Worcestershire sauce, honey and red pepper flakes. Whisk it until it all becomes one consistent mixture and set in the fridge, seal it if possible.
Now set your smoker at 225 degrees for smoking with apple wood chunks.If you do not have a smoker, see the bottom notes for alternatives! In a large mixing bowl combine these ingredients for your meatloaf. The ground chuck (80/20), milk, red onion (use your cheese grater to grate the red onion), Jack Daniels, Worcestershire sauce, crumbled saltine crackers (I place them in a zip lock bag and roll with a rolling pin), cayenne pepper, garlic powder, beaten eggs and the homemade Jack Daniels sauce. Now mix until it is combined nicely but do not over work the meat.
On a medium sized grill pan (make sure it has holes on the bottom for dripping) place half of your meatloaf and form a solid base. Create a little dent along the meatloaf and add the cheese, if you are using slices make sure you fold them in halves. Once the cheese is placed add the remainder of the meatloaf and form it with your hands. Also, make sure there are not any holes, the cheese will melt through.
Add 2/3 of your Jack Daniels glaze and brush for a good coating.
Add to the smoker and forget about it for 4 hours, or an internal temp of 165 degrees. I like to set another coat of the glaze 2 hours in.
Once the meatloaf is finished let it rest under aluminum foil for 8-10 mins at room temp and then slice 1/2-1” thick slices for serving.
Enjoy with family and friends!