I start by stirring the Oreo crumbs and melted butter together in a bowl until every crumb looks moistened. Then I press the mixture firmly into the bottom and up the sides of my greased tart pan using the back of a spoon. Popping it in the fridge for a few minutes while I prep the filling helps it firm up nicely.
In a large bowl, I beat the softened cream cheese with sugar, cocoa powder, vanilla, and milk until it's completely smooth with no lumps. I gently fold in the Cool Whip by hand rather than the mixer, which keeps the mixture light and airy. This step is really what gives the tart its mousse-like texture.
Once the filling is ready, I spread it evenly over the chilled crust using an offset spatula, smoothing the top so it's level. A flat surface here makes the ganache layer look much neater later on, so I try not to rush this part.
I combine the heavy cream and semi-sweet chocolate chips in a bowl, then microwave in 15-second bursts, stirring between each one, until it's fully melted and glossy. I pour this over the chilled filling and spread it out evenly, right to the edges of the crust.
For the web itself, I melt the white chocolate chips with a splash of heavy cream the same way, then transfer it into a piping bag. Starting at the very center of the tart, I pipe a spiral of white ganache all the way out to the edge, keeping the lines fairly close together.
This part looks fancy but is honestly the easiest step. I take a toothpick and drag it from the center of the tart straight out to the edge, repeating this about eight times around the spiral. Each drag pulls the white ganache into the classic cobweb pattern.
I melt orange candy melts and pipe six "L" shaped legs per spider onto parchment paper, letting them set for a few minutes. Then I attach three legs to each side of a round candy melt body with a small dot of melted candy, holding each leg for about 30 seconds until it sticks.
Once the spiders have set, I melt a few mini chocolate chips and pipe tiny dots on for eyes. I place the finished spiders on top of the web, then refrigerate the whole tart until I'm ready to slice and serve it.