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First, place 22 Jello Shot cups on a baking sheet.
Pour the vanilla vodka, coffee liqueur, espresso powder, and simple syrup into a spouted mixing bowl and mix well.
Slowly sprinkle the gelatin on top of the vodka mixture making sure to sprinkle it evenly across the top of the liquid.
Let the gelatin mixture sit for 7 minutes.
In the meantime, boil the water.
Add the boiling water to the gelatin mixture and stir until the gelatin is dissolved, at least 3 minutes.
Slowly pour the mixture into your Jello Shot cups until they are ⅔ full.
Refrigerate for 1 hour before starting the top layer.
Pour the Whipped Cream Vodka and water into the spouted mixing bowl and slowly sprinkle the gelatin on top.
Let the gelatin absorb the liquid for 5 minutes.
In the meantime, boil the water.
Add the boiling water to the gelatin mixture and stir until the gelatin is dissolved, at least 3 minutes.
Now add the sweetened condensed milk and stir well.
Let the cream Jello Shot mixture cool for 10 minutes.
Carefully pour a small amount of the cream Jello Shot mixture on the top of each espresso Jello Shot base.
Refrigerate at least 2 hours before placing the caps on the Jello Shot cups.
Serve Chilled. Can be made 2 days in advance.