Preheat the oven to 450°F (230°C) and prepare a baking sheet or use an oven-safe skillet.

In a mixing bowl, beat the cream cheese until smooth. Stir in the Monterey Jack, sharp cheddar, Worcestershire sauce, garlic powder, onion powder, dried parsley, and paprika until well combined.

Pat the chicken breasts dry with paper towels. Cut a deep pocket into each breast, being careful not to slice through completely. Season the outside of the chicken with salt and pepper.

Spoon half of the cheese filling into each chicken pocket, pressing the edges together to seal. Secure with toothpicks if needed.

Heat the olive oil and butter in an oven-safe skillet over medium-high heat. Sear the stuffed chicken breasts, skin-side down, for 3-4 minutes until the skin is golden brown.

Flip the chicken over and transfer the skillet to the preheated oven. Bake for 15-18 minutes, or until the internal temperature reaches 165°F (74°C) and the cheese is bubbly.

Remove the chicken from the oven and let it rest for 5 minutes. Remove any toothpicks, garnish with chopped fresh parsley if desired, and serve hot.