Set up dredging station: Whisk together the egg, Italian seasoning, Parmesan, salt, and pepper in one shallow bowl. Combine plain breadcrumbs, Panko, Parmesan, Italian seasoning, oregano, parsley, salt, and pepper in a second bowl.

Bread the chicken: Dip each cutlet in the egg wash, letting excess drip off, then press into the breadcrumb mixture to coat fully on both sides. Place on a plate and rest for 10 minutes.

Fry the chicken: Heat 2 tablespoons oil in a large skillet over medium-high heat. Fry chicken in batches without overcrowding for 3 to 5 minutes per side until deeply golden and cooked through to 165 degrees F. Transfer to a rack or paper towels.

Cook the pasta: Bring a large pot of salted water to a boil. Cook pasta until al dente. Reserve 1/2 cup pasta water before draining. Set aside.

Make the creamy pesto sauce: In a deep skillet over medium heat, melt the butter. Add garlic and cook for 1 minute until fragrant. Stir in pesto and warm for 1 minute. Pour in heavy cream, stir in cream cheese and freshly grated Parmesan. Simmer on low, stirring, for 3 to 4 minutes until sauce thickens. Season with salt, pepper, and red pepper flakes.

Combine pasta and sauce: Add drained pasta to the pesto sauce and toss to coat. Add reserved pasta water a splash at a time to loosen if needed.

Serve: Slice the crispy chicken and lay over plated pasta. Garnish with extra Parmesan and dried parsley. Serve immediately.