Preheat oven to 425 F. Grease 4 ramekins.
In a large, microwave-safe bowl, microwave chocolate and butter on high for 1 minute, or until butter has melted. Whisk together butter and chocolate until chocolate has melted and is incorporated.
Add the powdered sugar, and whisk until combined. Whisk in the eggs, yolks, and vanilla until well-combined. Add flour, and whisk until just combined
Pour batter into prepared ramekins and add 2 tablespoons pie filling over batter.
Set ramekins on a rimmed baking sheet. Bake for 12-14 minutes, or until the edges are firm but the center is still soft
Remove from oven and let the cakes stand for 1 minute. Run a thin knife around the edge to loosen cakes, and invert onto plate.
Top each cake with an additional 2 tablespoons pie filling and whipped cream. Serve warm.
To make ahead, prepare as directed through step 7. Cover ramekin with plastic wrap, and refrigerate for up to 1 day. To bake, set out ramekins while you preheat the oven then bake as directed.