In a mixing bowl, combine 1 cup of heavy whipping cream, 2 tablespoons of powdered sugar, and 1 teaspoon of vanilla extract. Beat on medium-high speed until soft peaks form, about 3-5 minutes. Set aside.

In another bowl, let 8 ounces of softened cream cheese sit at room temperature for about 10 minutes. Beat until smooth and creamy, about 2-3 minutes.

Gently fold the whipped cream into the cream cheese mixture, adding the whipped cream in thirds, ensuring to maintain the volume.

Stir in ½ cup of mini chocolate chips into the fluffy filling, ensuring they are well distributed without overmixing.

Spoon the mixture into the prepared graham cracker crust, spreading it evenly. Cover and refrigerate for at least 4 hours or overnight.

Once set, slice the pie into wedges and garnish each slice with fresh cherries and optionally a dollop of whipped cream or a drizzle of chocolate sauce.