For the pudding: Preheat the oven to 425 degrees F. Line a baking sheet with parchment and spray the parchment with cooking spray.
Thinly slice the bananas crosswise, about 1/8 inch thick. Toss the bananas in a bowl with the cinnamon and a pinch of salt. Place in a single layer on the prepared baking sheet. Bake until the bananas start to brown on the edges, about 10 minutes.
In a saucepan, whisk together the granulated sugar, flour and 1/2 teaspoon salt. Stir in the whole eggs and yolks, and then stir in the milk. Cook uncovered, stirring often, until the mixture thickens, about 10 minutes. Remove from the heat and stir in the vanilla.
Spread a thin layer of the pudding in a 1 1/2-quart casserole dish. Arrange a layer of sandwich cookies on top of the pudding, and arrange a third of the roasted banana slices over the cookies. Spread a third of the remaining pudding over the bananas and continue layering cookies, bananas and pudding, ending with pudding, so you have 3 layers total. Cover and refrigerate for at least 1 hour and up to overnight.
Whip together the heavy cream and confectioners' sugar in a medium bowl with an electric mixer to stiff peaks. Spread over the banana pudding.
For the ganache: Place the chocolate in a heatproof bowl. Heat the cream until hot but not simmering. Pour over top of the chocolate and let sit for a minute before stirring to melt and combine. Drizzle the ganache over the pudding. Spoon the pudding into bowls and serve chilled or at room temperature.