Put graham crackers in a large resealable plastic bag, and crush them with a rolling pin until very fine crumbs form.
Pour crumbs into a medium bowl; stir in sugar. Add butter, and stir until well combined.
Press the crumb mixture into shot glasses, spreading it up the side; press flat. Chill crust in freezer at least 10 minutes.
Meanwhile, make the filling: Using an electric mixer set at medium-high speed, beat the cream cheese in a large bowl until smooth. Beat in the condensed milk a little at a time, scraping the sides of the bowl as necessary. Beat in the lemon juice and vanilla.
Pour the filling into the crust; freeze for 10 minutes and then decorate with cherry pie filling and whipped cream.
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