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In the bowl of a stand mixer, whip chilled cream, sugar and vanilla together until soft peaks form. Measure out 3 cups of whipped cream and refrigerate remaining whipped cream to serve as topping.
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In a small bowl, whisk together pudding mix and two cups of milk.
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Rinse the bowl of the stand mixer and using paddle attachment, beat together softened cream cheese and sweetened condensed milk until smooth.
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Add pudding to stand mixer and continue to stir until combined.
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Then, gently fold in 3 cups of homemade whipped cream.
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To assemble banana pudding:
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Line bottom of 9x13 casserole dish with 20 Chessmen cookie.
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Slice bananas and arrange over cookies.
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Spread pudding mixture over bananas.
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Finally arrange another layer of 20 Chessmen cookies on top of pudding mixture.
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Cover and refrigerate for 2-3 hours or until chilled through.
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Serve with additional whipped cream if desired.