Stir the crushed cookies, melted butter, and 1 tablespoon sugar until the crumbs look evenly moistened. Divide the mixture among 6 clear cups or dessert glasses (about 8-ounce size). Press gently with the back of a spoon to form an even layer. Set aside.
Toss the sliced strawberries with 2 tablespoons sugar and the lemon juice in a bowl. Let them sit 10–15 minutes until they release a light syrup and look glossy. Stir once halfway through.
Beat the softened cream cheese, powdered sugar, and vanilla with a hand mixer until smooth and free of lumps. In a separate bowl, whip the cold heavy cream to soft peaks. Gently fold the whipped cream into the cream cheese mixture until the filling looks uniform and fluffy. Avoid overmixing so it stays light.
Spoon a layer of the cream filling over each cookie base. Add a generous spoonful of macerated strawberries and a little of their syrup. Repeat with another layer of cream and finish with strawberries on top. If desired, sprinkle a few extra cookie crumbs.
Cover the cups loosely and refrigerate at least 1 hour. The flavors meld and the base softens into a cake-like texture. Serve cold.