Line a 9×5 inch loaf pan with plastic wrap and set it aside.
In a small saucepan, combine cherries, 2 tablespoons of sugar, and bourbon. Bring to a boil, then simmer for about 2 minutes. In a small bowl, whisk together lemon juice and cornstarch; add to cherry mixture and cook until thickened. Remove from heat, mash cherries, and chill in the fridge.
In a stand mixer, whip 1 pint of heavy cream with ½ cup sugar and vanilla extract until soft peaks form. Transfer to a bowl.
Add mascarpone and cooled cherries to the stand mixer; beat until combined. Fold this mixture into the whipped cream.
Spread ⅓ of the whipped cream mixture on the bottom of the loaf pan. Stand a layer of cookies along the pan’s outside, forming three rows. Create 15 sandwiches with the remaining cookies and cream, then place them in the pan.
Fill any gaps with extra cookies and spread the remaining cream on top. Wrap tightly with plastic wrap and chill in the fridge for at least 4 hours, or overnight. For easier slicing, freeze for 1-2 hours after the initial chill.
When ready to serve, whip the remaining cream with sugar and vanilla until medium peaks form.
Unwrap and invert the cake onto a platter, then pipe or frost with whipped cream. Garnish with shaved chocolate and fresh cherries before serving. Enjoy!