In a small bowl, mix the cookie crumbs with the melted butter. Set aside.
Pit and slice the cherries in half.
To a blender, add pitted cherries, water, and 2 tbsp sugar. Blend until puréed. Remove and place in a large bowl.
To the blender, add cream cheese, milk, and the remaining 6 tbsp of sugar. Blend until smooth.
In a bowl, mix cream cheese mix with the cherry mix.
Pour the mixture into the popsicle molds, filling up the molds only 2/3rds of the way.
Top with cookie mixture and gently press into the mold. Leave about 1/2 inch of space at the top for the popsicles to expand. Close top and insert popsicle sticks.
Freeze for at least 8 hours (preferably overnight).
To serve, run the popsicle mold under warm water for 5-10 seconds to easily remove the popsicles.