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Preheat oven to 425 degrees. Lightly grease a large baking sheet pan.
Wash and dry potatoes, then slice into THIN wedges. (You should have 8-10 wedges per potato - if you cut them too thick they won't get crispy and might not cook through completely) Place potato wedges in a bowl. Drizzle with 1 1/2 tablespoons of oil and toss to coat.
In a small bowl stir together garlic powder, Italian seasoning, salt, pepper, and parmesan cheese. Pour half of the mixture into the bowl with the potatoes and toss to combine. Set aside remaining seasoning.
Arrange potatoes on prepared pan so that none of the potatoes are overlapping and they are all laying on their side (not standing up so that the skin-side is touching the pan). Bake in preheated oven for 15 minutes. Meanwhile prepare the chicken...
Brush chicken with remaining oil, then sprinkle on both sides with remaining seasoning mixture.
After the potatoes have cooked for 15 minutes, remove them from the oven and reduce oven temperature to 400 degrees. Use a fork to flip each potato wedge over to the other side. Scoot all of the potatoes towards the edges of the pan to make room for arranging the chicken on the pan.
Return to oven for 15-20 minutes until chicken is cooked through and potatoes are fork-tender and crispy on the outside.
Top chicken and potatoes with additional parmesan cheese if desired and serve with ketchup or ranch dressing.