In a medium saucepan, whisk together the sugar, cocoa powder, cornstarch, cinnamon, espresso powder, chili powder, egg, and chocolate chips.
Place pan over medium heat and whisk in the milk. Continue whisking until the mixture comes to a boil. Allow it to boil for 1-2 minutes, whisking constantly, until mixture thickens significantly.
Remove from heat and whisk in butter and vanilla. Continue whisking until the butter is completely melted.
Spoon the pudding evenly into 6 ramekins or dessert glasses and smooth the tops. Place waxed paper directly on the surface of each pudding to prevent skin from forming. Refrigerate until well chilled, at least 2 hours.
Top with homemade whipped cream and then a light sprinkle of additional cinnamon, espresso powder, and chili powder, for garnish.