Preheat and prep: Heat your oven to 400°F (200°C).
Line a baking sheet with parchment or lightly grease a baking dish. Pat the chicken breasts dry with paper towels.
Make the seasoning butter: In a small bowl, combine melted butter, olive oil, minced garlic, smoked paprika, onion powder, garlic powder, thyme, salt, and pepper. Stir until smooth.
Cut a pocket: Place a chicken breast flat on a cutting board.
Using a sharp knife, slice a deep pocket along the thickest side, keeping the knife parallel to the board. Don’t cut all the way through. Repeat with the remaining breasts.
Stuff the filling: If using cream cheese, mix it with the cheddar to help it bind.
Stuff about 1.5 oz of cheddar (and a portion of cream cheese, if using) into each pocket. Press the edges together and secure with toothpicks. Don’t overfill or it will leak.
Season well: Brush or spoon the seasoning butter all over the chicken, including a little inside the pocket. Make sure each piece is evenly coated.
Quick sear (optional but recommended): Heat a large oven-safe skillet over medium-high heat.
Add a drizzle of oil and sear the chicken 1–2 minutes per side until lightly golden. This step boosts flavor and helps seal edges. If skipping, go straight to baking.
Bake to juicy perfection: Transfer chicken to the prepared baking sheet or keep in the skillet.
Bake for 18–22 minutes, depending on thickness, until the internal temperature reaches 165°F (74°C) at the thickest part.
Rest and garnish: Let the chicken rest 5 minutes. Remove toothpicks carefully. Garnish with chopped parsley or chives.
Slice and serve.