Preheat oven to 300 degrees.

Prepare the popcorn according to the instructions on the bag. Pour popcorn into a large bowl, making sure to pick out any kernels that didn't pop before adding it to the bowl. Spray two spatulas with cooking spray and set aside.

Add sugar, water and corn syrup to a large saucepan and heat over medium-low until the sugar dissolves, stirring occasionally. Increase heat to high and boil without stirring until the mixture becomes a deep amber color, approximately 10-13 minutes. Remove from heat immediately and add cream (note the mixture will bubble up on you!). Stir until blended. Quickly stir in the peanuts and salt. Drizzle the caramel right away over the popcorn mixture and toss with the prepped spatulas until evenly combined.

Line a rimmed baking sheet with foil and coat with nonstick cooking spray (or use a Silpat).

Carefully transfer the caramel corn to the sheet and spread out in an even layer, being very careful not to touch the caramel with your bare hands.

Place caramel corn in oven and bake until caramel is shiny and coats popcorn, tossing mixture occasionally, approximately 20 minutes. Cool completely, tossing every so often to break up large clumps. While the caramel corn is cooling, heat the chocolate in a microwave-safe bowl in the microwave for 30-second increments, stirring in between, until it is all melted. Drizzle over the caramel corn and let the chocolate set in the refrigerator, approximately 20 minutes.