Take a strawberry and split it down the center lengthwise, keeping the stems attached. Take a small piece off of the fat rounded side so when you set it down, it rests flat as opposed to rolling around. Using a small paring knife or melon baller, carve out a very small piece of strawberry flesh on the flat side of the strawberry to create a small bowl. This is where you'll pipe your filling. Repeat with remaining strawberries.

In the bowl of a stand mixer with the whisk attachment, whip the heavy whipping cream on high speed until stiff peaks form, about 5-7 minutes. Scrape out of the bowl and place in a medium bowl; set aside. Back in the stand mixer bowl, add in the cream cheese, confectioners' sugar and vanilla. Beat on medium speed until fluffy and creamy, about 1 minute. Fold in the whipped cream until no streaks remain and everything is incorporated.

Fill a piping bag with the cheesecake mixture. Pipe the cheesecake mixture into the 'bowl' of the strawberry you created. Immediately sprinkle with graham cracker crumbs. Cover and refrigerate or serve immediately.