Preheat oven to 450˚F with a nonstick popover pan on the rack in the lowest position.
First, make the caramel. In a large skillet over medium-high heat, combine sugar and corn syrup, stirring occasionally, until the sugar is dissolved, approximately 8-10 minutes. The mixture will be a dark amber.
Reduce heat to medium. Slowly add the heavy cream, bourbon and butter to the skillet (be careful, it will splatter a bit!). Cook, stirring constantly, until combined, approximately 3-4 minutes.
Remove from heat and set aside.
In a large bowl. whisk together eggs, milk and vanilla until frothy, approximately 1 minutes.
Add flour, salt, sugar, and ground cinnamon to the egg mixture. Whisk until the batter comes together with some small lumps still remaining. Gently fold in chopped apple.
Remove popover pan from the oven and coat with cooking spray. Fill popover cups approximately 3/4 full with batter.
Bake 20 minutes, then reduce heat to 350 degrees and bake an additional 20 minutes until golden brown.
In the last 5 minutes of baking, reheat the caramel over low heat until smooth and creamy again.
Remove popover pan from the oven and carefully remove the popovers from the pan onto a wire rack.
Serve immediately with bourbon caramel.