Using a stand mixer or electric mixer, combine heavy cream and powdered sugar. Beat until stiff. Set aside.
Beat the cream cheese and vanilla extract until creamy and blended. Fold half of the whipped cream into the cream cheese gently until combined. Set aside.
Mix together the milk and pudding mix. Beat on high for 2 minutes.
In an 8x8 baking dish, line with 4 graham crackers in a single layer, breaking/slicing as needed to fit. I found that using a serrated steak knife cut cleanly without breaking into pieces. Next, spread the cream cheese mixture evenly. Add cherries cut side down in rows on the cream cheese mixture.
Layer more graham crackers on top. Now, add pudding and spread evenly. Place one more layer of graham crackers on the pudding.
Top with whipped cream and spread evenly.
Cover and refrigerate overnight (or at least 4-6 hours).