Combine the crushed cookies, sugar, and melted butter in a bowl until moistened and well-blended. Divide the mixture evenly among the glasses. Gently press the crumbs to the bottom of the glass.

In the bowl of a stand mixer, beat the softened cream cheese until fluffy and smooth (no more lumps). Adjust the speed to low then add the pumpkin puree, sugar, pumpkin spice, and vanilla extract. Beat until everything is smooth and well-blended.

In a heat-proof bowl over barely simmering water, melt the chocolate and butter. Stir often. Let it cool for a couple of minutes afterward.  To the pumpkin mixture add the cooled chocolate. Beat together until well-blended and creamy.

Whip the cream and sugar until stiff peaks form. I am using freshly whipped cream with sugar to ensure that the cream holds up and doesn't flop.

To assemble, spoon enough pumpkin cheesecake onto the cookie crust. Layer with some freshly whipped cream and then top with another spoon or two of the pumpkin cheesecake. Refrigerate for at least an hour or two to firm up more. This can be made a day ahead. Serve on top with a little broken spiced cookie as garnish. Enjoy!