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. Using a small paring knife or melon baller, carve out a small piece of strawberry flesh on the flat side to create a bowl.
In 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 and set aside in a medium bowl.
Add cream cheese, confectioners' sugar, and vanilla to the stand mixer. Beat on medium speed until fluffy, about 1 minute. Fold in the whipped cream until no streaks remain.
Fill a piping bag with the cheesecake mixture and pipe it into the strawberry bowls. Sprinkle with graham cracker crumbs. Refrigerate or serve immediately.