Add heavy whipping cream to a mixer bowl and beat until stiff peaks form, refrigerate immediately.
Next, add softened cream cheese, powdered sugar and vanilla to a mixer bowl and beat until smooth.
Wash strawberries and dry with paper towels. Set 6 whole berries aside for garnish.
Dice 1 cup of strawberries and slice remaining strawberries.
Fold 1 cup diced strawberries and whipped cream into cream cheese mixture until well combined.
Add cheesecake mixture to a piping bag without the tip or a zip top bag with one corner snipped.
Add 1/2 tablespoon graham cracker crumbs to each glass.
Top each with a bit of cheesecake mixture, filling about 1/3 full.
Layer a few sliced strawberries over filling.
Add 1/2 tablespoon graham cracker crumbs.
Repeat with filling, sliced strawberries and finish with cheesecake filling.
Garnish each with a whole strawberry.
Refrigerate 2 hours before serving.